Tobacco Documents Online

Authors: G. D. Byrd Date: September 11, 1989 J. N. Schumacher M. F. Borgerding ----- >K. W. Fowler M. E. Lovette Department: New Products Technology Notebook Pages: None Project No. and Title: 0218, Alpha R&DM, 1989, No. 251 Previous Reports: R&DM, 1987, No. 30 No. of Pages: 51 EBPANSION OF T8E TOBACCO/SMOKE MASS SPECTRAL LIBRARY (TOBACCO.L) OBJECTIVES: • To expand the number of compounds in the existing TOBACCO.L mass spectral library. • To create a spreadsheet for retention times of compounds in TOBACCO.L using standard conditions for both polar and nonpolar GC columns. i SUMMARY: The TOBACCO.L mass spectral library has been expanded to over 2,200 entries and a retention time spreadsheet has been created for many of the compounds. The spreadsheet includes retention times using standard polar and nonpolar GC conditions. The additional compounds were selected based on their occurrence in tobacco, tobacco smoke, and related samples. STATUS: As of September 5, 1989, there were 2,209 entries in the library and spreadsheet. Addition of new compounds and retention times will occur as time permits. Copies of the mass spectral library can be made available on CS80 tape, 3.5" floppy disk, or 20 megabyte Bernoulli cartridge.. Copies of the retention time spreadsheet can be made available on 3.5" or 5.25" floppy disks. NS KEYWORDS: Mass spectral library, mass spectrometry, gas chromatography, retention time spreadsheet, tobacco, smoke 1

This system has proven extremely useful in identifying chemical components in smoke and flavors from new products. We believe that this system could also be useful to others here at R. J. Reynolds R & D. EXPERIMENTAL Gas chromatography. Two columns, one polar and one nonpolar, were used to generate retention times. Both columns were commercial fused silica columns and each was operated under its own specific temperature programming parameters. The polar column was a 30 m x 0.25 mm fused silica capillary column with a 0.25 µm polyethylene glycol bonded film (DBWAX-30N, J&W Scientific, Folsom, CA). The GC oven was temperature programmed as follows: initial temperature initial time program rate final temperature = 37'C = 2 min = 2.5'C/min = 230'C The usual total run time was 95 min. The carrier gas was helium and the column head pressure was approximately 60 kPa using a direct interface to the mass spectrometer. Column back pressure was adjusted such that the retention times of pyrazine, nicotine, and glycerol were 13.2 ± 0.1 min, 44.3 ± 0.1 min, and 62.2 ± 0.1 min, respectively. The nonpolar column was a 60 m x 0.32 mm fused silica capillary column with a 5.0 µm methylsilicone bonded film (DB1- 60W, J&W Scientific, Folsom, CA). The GC oven was temperature programmed as follows: initial temperature = 35•C initial time = 10 min program.rate = 2.5•C/min final temperature = 275°C The usual total run time was 110 min. The carrier gas was helium and the column head pressure was approximately 90 kPa using a direct interface to the mass spectrometer. Column back pressure was adjusted such that the retention times of 2-propanol, toluene, octanal, and nicotine were 12.5 ± 0.1 min, 40.8 ± 0.1 min, 60.0 ± 0.1 min, and 86.8,t 0.2 min, respectively. Mass spectrometrv. The mass spectrometer used in these studies was a Hewlett-Packard HP 5970B "Mass Selective Detector"(Hewlett-Packard Company, Palo Alto, CA). This instrument is a quadrupole mass spectrometer with a scanning range of 10-800 u. Scanning range and rate were selected based on the sample or. standard analyzed.

Data system. The GC/MS system was controlled by a Hewlett- Packard HP 59970C ChemStation using revision 3.1.1 of the Pascal operating system. The mass spectral library editor (2] was used to enter spectra into the mass spectral library which was named "TOBACCO.L". For each spectrum entered the editor records the ten most significant peaks. The significance of a peak is its mass multiplied by its abundance. The library editor can also be used to search unknown compounds against the library. This editor uses a forward search algorithm based on the ten most significant peaks in the spectrum as defined above. Because entries cannot be deleted from the library once they are entered, multiple entries are included in the library for some compounds. However, these do not create problems during the search algorithm. Retention spreadsheet. A spreadsheet of retention times for comounds in the mass spectral library was maintained on an IBM PCt compatible computer using the Lotus i-2-3t'" spreadsheet program, Release 2 (Lotus Development Corporation, Cambridge, MA). Each entry included the compound number (which is the same as in TOBACCO.L), compound name, Chemical Abstract (CAS) Registry Number, molecular weight, and retention times on the DBWAX and DB1 columns. The spreadsheet file is named "TOBACCO.WK1". RESULTS AND DISCUSSION The compounds included in this library are generally tobacco and smoke related. Common solvents and impurities which might be expected in samples were also added. Table 1 summarizes the information in the spreadsheet as of September 5, 1989. The library contains over 2,200 entries but this includes duplicates and some compounds with only a partial identity. Duplicates account for 11% of the total entries and CAS registry numbers are given for 90% of the unique compounds. DBWAX retention times are available for 49% of the entries and DB1 retention times for 19% of the entries. A complete listing of TOBACCO.WK1 is given in Appendix 1 sorted alphabetically by compound name. Listing of compounds. Each entry has a unique compound number that is the same in TOBACCO.L and TOBACCO.WK1. Because of duplicate entries, multiple entry numbers exist for some compounds. It is possible that a compound may be entered twice and named in a different manner each time. In these cases the CAS number should be checked to verify the structure. Most compounds in TOBACCO.WK1 are named using a modified form of the IUPAC name. The modification was necessary to allow for logical alphabetizing of the names. For example, the IUPAC name for acetone is "2-PROPANONE" but is entered as "PROPANONE- 2". Substituents are listed by the primary root first followed by the position and name of substituents. An example of this is "PYRIDINE, 2,6-DIMETHYL-". When multiple functionalities occur 4

in a compound, their position is indicated by inserting the number just before the functionality as in "HEPTANE-2,6-DIONE". Some compounds are listed only by their common name such as "MYOSMINE", "MARIOLIDE", etc. When possible, both names are entered with the common name in parentheses following the IUPAC name. Most of the entries for which no CAS number is listed are only partially identified. In some cases the precise isomer (cis or trans) of the compound is not known. Certain codes that have been used historically at the R. J. Reynolds Tobacco Company have carried over into this library. These codes are listed in parentheses after the compound name. In some cases, only the code is listed for the compound and the exact structure is unknown. The most prevalent codes used are the "S-series" and refer to isolation work done on tobacco and smoke. These codes can be generally explained as follows for the example of entry #60, "SR43C". The "S" designates the division where the work was done. "R" is the code for the person who did the work and "43" is the compound number. "C" indicates that the compound is an isolate from tobacco. A "D" would have indicated that the compound was isolated from smoke. Use of mass spectral searches. The-results from a mass spectral library search should be used with basic skills in interpreting mass spectra to identify a compound. Each component must be reviewed individually to see if the spectrum is logical and consistent with the chromatography of the particular system. Practice has shown that the TOBACCO.L library is faster and usually more accurate in our work than the 10 peak NBS reference library (NBS REVE.L) offered by Hewlett-Packard. Consequently, we tend to search TOBACCO.L first. However, the use of other libraries and other searching algorithms can assist in solving identities when TOBACCO.L cannot. A macro for searching three different libraries and displaying the results was written and is listed in Appendix 2. In addition to the 10 peak searches for TOBACCO.L and NBS REVE.L, this macro offers access to a probability-based matching algorithm [3] that can be used with Hewlett-Packard's NBS REVF.L library. Use of retention times. The retention times listed in TOBACCO.WK1 were produced on systems that were calibrated as described in the experimental section. Practice has shown that retention times will shift in actual samples by as much as a minute. Factors affecting this are solvent, manner of injection (split or splitless), and instrumental variability. This should be kept in mind when matching retention times for unknowns. The primary purpose of the retention times here is to provide more confidence in the assignment of a particular structure. Homogolous series. In cases where a good mass spectral match is obtained but no retention time is available, it is useful to guess what type of retention behavior might be 5

expected. Several homologous series of selected compounds have been extracted from TOBACCO.WK1 and are plotted as retention time versus carbon number. Table 2 lists these compounds and the corresponding plots are shown in Figures 1-8. G. D. rd F. B M"v Submitted: September 11, 1989 Approved: ac.. q/IZ~SS Accepted : ~ O~j DISTRIBUTION Dr. M. F. Borgerding Dr. G. D. Byrd Dr. H. L. Chung Dr. E. L. White Dr. B. M. Lawrence Dr. M. W. Ogden Mr. R. W. Williams a. °Yt . S tm"& J. . Schumacher K ler • n; •; • Dr. G. R. DiMarco Dr. W. M. Hildebolt Dr. R. A. Lloyd Dr. M. E. Stowe Dr. A. W. Hayes Mr. L. A. Lyerly Ms. B. T. Hodge Mr. K. L. Rush Dr. B. M. Gordon Dr. C. R. Ashcraft 6

REFERENCES 1. Schumacher, J. N. and Murphy, J. J., "Tobacco/Smoke Mass Spectral Library", RDM, 1987, No. 30. 2. HP 59970C ChemStation Operator's Manual, Hewlett-Packard Company, Palo Alto, CA, Publication No. 59970-90016, March 1986. 3. MacLafferty, F. W., InterRretation of Mass Svectra, 3rd Edition, University Science Books, Mill Valley, CA, pp.. 232- 233 (1980). 7

TABLE 1: Information Available in TOBACCO.WK1 Spreadsheet as of September 5, 1989. Total Number of Entries = 2,209 Number of Unique Entries = 1,975 Number of Compounds with CAS No. = 1,772 Number of Compounds with DBWAX R. T. = 975 Number of Compounds with DB1 R. T. = 377 8

TABL E 2: Homogolous Series from TOBACCO.WK1 Retention Times°. ALKA NES ALCOHOLS C# COMPOUND DBWAX DB1 C# --- COMPOUND ------------- DBWAX ------ DB1 ------ 1 Methane 1 Methanol-1 3.2 6.3 2 Ethane 2 Ethanol-1 3.9 11.4 3 Propane 3 Propanol-1 6.8 17.6 4 Butane 4 Butanol-1 10.9 -28.3 5 Pentane 5 Pentanol-1 15.5 38.8 6 Hexane 1.5 23.7 6 Hexanol-1 20.4 48.4 7 Heptane 1.7 34.3 7 Heptanol-1 25.8 57.2 8 Octane 2.2 44.3 8 Octanol-1 30.8 65.8 9 Nonane 3.4 53.3 9 Nonanol-1 35.5 73.2 10 Decane 5.6 61.6 10 Decanol-1 41.0 80.0 11 Undecane 9.4 69.3 il Undecanol-1 45.4 86.5 12 Dodecane 13.8 76.6 12 Dodecanol-1 49.6 13 Tridecane 18.9 83.1 13 Tridecanol-1 53.7 14 Tetradecane 22.5 89.2 14 Tetradecanol-1 57.7 15 Pentadecane 29.5 15 Pentadecanol-1 61.4 16 Hexadecane 33.1 100.3 16 Hexadecanol-1 65.2 17 Heptadecane 39.1 17 Heptadecanol-1 18 Octadecane 42.9 18 Octadecanol-1 71.5 19 Nonadecane 47.4 19 Nonadecanol-1 20 Eicosane 51.6 20 Eicosanol-l 78.4 21 Heneicosane 55.3 21 Heneicosanol-1 22 Docosane 59.3 22 Docosanol-1 85.4 23 Tricosane 62.7 24 Tetracosane 66.2 25 Pentacosane 69.7 26 Hexacosane 72.3 27 Heptacosane 28 Octacosane 78.5 29 Nonacosane 30 Tricontane 86.2 31 Hentriacontane 32 Docotricontane 96.2 °Plots of Carbon Number versus Retention Time are shown in Figures 1-8. 9

TABLE 2, continued ALDEHYDES KETONES-2 C# COMPOUND DBWAX DB1 C# COMPOUND DBWAX DB1 --- ------------- ------ ------ --- ------------- ------ ------ 1 Methanal 1 Propanone-2 2.4 11.4 2 Ethanal 1.8 6.2 2 Butanone-2 3.2 20.6 3 Propanal 2.1 11.7 3 Pentanone-2 4.8 30.4 4 Butanal 2.9 21.0 4 Hexanone-2 8.6 40.9 5 Pentanal 6.2 31.6 5 Heptanone-2 11.9 50.2 6 Hexanal 8.9 42.0 6 Octanone-2 17.1 59.1 7 Heptanal 12.0 51.5 7 Nonanone-2 22.3 67.1 8 Octanal 16.7 60.0 8 Decanone-2 27.4 74.4 9 Nonanal 22.0 67.9 10 Decanal 27.6 75.3 11 Undecanal 32.3 82.0 12 Dodecanal 37.6 88.3 13 Tridecanal 42.7 94.4 14 Tetradecanal 47.7 100.3 ACID S METHYL ESTERS C# COMPOUND DBWAX DB1 C# COMPOUND DBWAX DB1 ------ ------ --- ------------- ------ ------ 1 Formic 1 Formate 2 Acetic 24.6 21.0 2 Acetate 2.4 15.1 3 Propanoic 29.1 30.9 3 Propionate 4 Butanoic 4 Butanoate 5 Pentanoic 5 Pentanoate 6 Hexanoic 6 Hexanoate 7 Heptanoic 48.4 7 Heptanoate 8 Octanoic 8 Octanoate 9 Nonanoic 9 Nonanoate 27.4 10 Decanoic 60.1 83.0 10 Decanoate 33.1 11 Undecanoic 64.0 11 Undecanoate 12 Dodecanoic 67.5 12 Dodecanoate 42.7 13 Tridecanoate 14 Tetradecanoate 51.5 NITR ILES ALKENES-1 C# --- COMPOUND ------------- DBWAX ------ DB1 C# --- COMPOUND ------------- DBWAX ------ DB1 ------ 2 Ethane 5.1 10.3 2 Ethene 3 Propane 5.9 17.4 3 Propene 4 Butane 8.6 28.2 4 Butene 5 Pentane 5 Pentene-1 1.4 12.6 6 Hexane 6 Hexene-1 1..6 22.5 7 Heptane 7 Heptene-1 8 Octane 28.4 65.9 8 Octene-1 2.5 43.1 9 Nonane 9 Nonene-1 3.9 52.3 10 Decane 10 Decene-1 6.5 10

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FIGURE 4 KETONES-2 + + + 2 + Z O I 40-I 20 -a~ 10-W 0-1 0 + I + 0 I + 0 0 I 0 0 0 i 6 8 10 12 t 96L6 9t0ZS CARBON NUMBER O DBWAX + DBI

FIGURE 5 ACIDS 110 100 -r 90 -1 + 70 0 0 0 f L6L6 9L9TS 10 -r 0 + 2 6 0 8 10 12 14 . 16 CARBON NUMBER 13 DBWAX + 0131

FIGURE 6 METHYL ESTERS 100-I 80 ~ 70-I 60 -~ S0 - 40 30 -a~ 20 -I 10 - 1 0 O' 2 4 6 : © + 0 0 10 12 14 16 18 CARBON NlJM8E3t 86L6 9Z0Z5 13 DBWAX + DB1

FIGURE 7 NITRILES 110, 100 90 #~• 80 -~ 2 70 -~ + v ~ W 60 -~ ~ 3 F z S0-I 0 I 30 -~ + O 20-+' + 10 --+ + ~ 0 0 0 I I I I I 6 8 14 CARBON NUMBER 66L6 9T0TS ~ DBWAX + DBI

FIGURE 8 AL.tcaNes-, CARBON NUMBER a DewAx + DBI 0096 9ti0t5

APPENDIX 1: TOBACCO.WK1 Retention Time Database Sorted by Compound. RT (min) CNPD ----------- S DBYAX DB1 1390 1.8 6.2 1468 719 1391 1392 44 1316 1559 191 747 1315 748 1317 367 1519 1322 322 310 1704 345 1319 1320 746 283 1321 1318 1930 5 2113 643 721 1573 19.6 41.0 36.7 718 1731 1386 2137 2170 2150 93 2159 2116 1481 1480 1482 1483 1393 801 1699 1720 1688 440 1178 1175 1177 1179 960 1176 1465 1345 1344 1532 1533 1228 237 1227 498 964 749 1632 1718 750 23.3 23.3 35.1 38.5 38.5 62.0 53.3 24.6 24.6 3.2 62.2 41.9 14.4 14.5 7.9 46.2 2.4 38.5 4.8 19.0 5.1 5.1 14.4 46.4 73.2 40.1 33.8 2.6 47.1 48.3 44.1 49.4 56.6 57.5 COMFOUND NAME MW CAS NtMBER ----------------------------------------------------------------------- ---- -----...----- ACETALDEHYDE ACETALDEHYDE, 3-PYRIDYL- ACETALDEHYDE, ACETYLOD(Y- (ACETIC ACID, GLYCOLALDEHYDE ESTER) ACETALDEHYDE, ANINO- ACETALDEHYDE, HYDROXY- (GLYCOALDENYDE) ACETAMIDE ACETANIDE, ACETAHIDE, ACETAKIDE, ACETAMIDE, ACETAKIDE, ACETAKIDE, ACETAMIDE, ACETAKIDE, ACETAMIDE, ACETAKIDE, ACETAKIDE, ACETAMIDE, ACETANIDE, ACETAMIDE, ACETAMIDE, ACETAMIDE, ACETAMIDE, ACETAMIDE, ACETAMIDE, ACETAMIDE, 44 75-07-0 121 42545-63-1 102 5371-49-3 59 6542-88-7 . 60 141-46-8 59 60-35-5 N,N-DIETHYL- 115 685-91-6 N,N-DINETHYL- 87 127-19-5 N,N-DIMETHYL- 87 127-19-5 N-2-PROPENYL- 99 692-33-1 N-ACETYL-N-METHYL- (NETHYLANINE, N,N-DIACETYL-) 115 1113-68-4 N-BUTYL- 115 1119-49-9 N-ETHYL- 87 625-S0-3 N-METHYL- 73 79-16-3 N-PROPYL- (SWT3D) 101 5331-48-6 N-PROPYL- (SWT3D) 101 5331-48-6 N-(1-NETHYLPROPYL)- (SW17DD) 115 1189-05-5 N-(2-FURAIIYLNETHYL)- (SW156D) 139 5663-62-7 N-(2-HYDROXYPROPYL)- 117 4293-57-6 N-(2-NETHYLBUTYU- (S{ht 182D) 129 54824-90-7 . N-(2-METHYLPROPYL)- 115 1540-94-9 N-(2-O)(OPROPYL)- 115 7737-16-8 N-(2-OXOPROPYL)- 115 7737-16-8 N-(2-PHENYLETHYL)- (S1Wl8D) 163 877-95-2 N-(2-PROPENYL)- 99 692-33-1 N-(3-NETHYLBUTYU- 129 13434-12-3 60 6i-19-7 60 64-19-7 1-METHYLETHYL ESTER 102 108-21-4 2-ACETYLOXY- 118 13831-30-6 2-HYDROXY-, 2-HYDRODCYPROPYL ESTER 134 61892-60-2 2-PHENYLETHYL ESTER 164 103-45-7 2-(2-FURYL)-2-ONOETHYL ESTER (SNN6iD) 168 19859-79-1 ANHYDRIDE (ACETIC ANHYDRIDE) 102 108-24-7 ANHYDRIDE (ACETIC ANHYDRIDE) 102 108-24-7 BUTYL ESTER 116 123-86-4 DODECYL ESTER 228 112'66-3 METHYL ESTER (NETHYL ACETATE) 74 . 79-20-9 PHENYLNETHYL ESTER 150 140-11-4 PROPYL ESTER 102 109-60-4 21.0 ACETIC ACID 21.0 ACETIC ACID 28.6 ACETIC ACID, 58.0 ACETIC ACID, ACETIC ACID, ACETIC ACID, ACETIC ACID, ACETIC ACID, ACETIC ACID, 43.6 ACETIC ACID, ACETIC ACID, 15.1 ACETIC ACID, ACETIC ACID, ACETIC ACID, 31.7 ACETONE OXINE 10.3 ACETONITRILE 10.3 ACETONITRILE 35.4 ACETONITRILE, 2-(N,N-DIMETHYLAMINO)- ACETONITRILE, HYDROXY- ACETONITRILE, OXO- ACETOPHENONE, 21,50-DIHYDRONY- (SNN71D) ACETOPHENONE, 2-HYDRONY-4-lR:THYL- ACETOPHENONE, 4-HYDROHY-3-IN:THOD(Y- ACETOPHENONE, 4-METHYL- 65.7 ACETOPHENONE (ETHANONE, 1-PHENYL-) ACRIDINE, 2-ETHYL- ACRIDINE, 3-METHYL- ACRIDINE, 4-ETHYL- ACRIDINE, 9,10-DIHYDRO- ACRIDINE, (PYRIDINE[b,e]DIBEN20-) ACRIDINE, (PYRIDINE[b,e]DIBEN20-) 12.3 ACROLEIN, (2-PROPENAL) ACRYLAHIDE, 2-METHYL- (PROPENANIDE-2, 46.1 ACRYLANIDE (PROPENAMIDE-2) 73 127-06-0 41 75-05-8 41 75-05-8 84 926-64-7 57 107-16-4 55 li471-47-0 152 490-78-8 150 6p21-64-8 166 496-02-2 134 122-00-9 120 V8-86-2 207 55751-83-2 193 4740-12-9 207 65789-44-8 181 92-81-9 179 260-94-6 179 260-94-6 56 107-02-8 2-METHYL-) 85 79-39-0 ACRYLIC ACID, 3-(2-FURANYLNETHYL)-2-NETHYL-, ETHYL ACRYLIC ACID, 3-(2-FURYL)-2-NETHYL-, ETHYL ESTER ANABASINE, N-FORNYL- ANABASINE, N-METHYL- (SN1M) ANABASINE, N-(1-OXOPENTYL)- ANABASINE (PYRIDINE, 3-(2-PIPERIDINYL)-) ANATABINE, NITROSO- ANATABINE, N-ACETYL- ANATABINE, N-ACETYL- ANATABINE, N-ETHYL- ANATABINE, N-FORMYL- 71 79-06-1 ESTER (isomer) 180 180 82826-13-9 190 71635-28-4 176 24380-92-5 246 62783-95-3 162 13078-04-1 189 7'1608-13-4 202 61892-64-6 202 61892-64-6 188 61892-98-6 188 61892-65-7 19

TOBACCO.WK1 Retention Time Database - Septeaber S, 1989 RT (min) CNPD ----------- Sorted by Coapotxd Name B DBWAX DB1 COMPOUND NANE Nil CAS NUIBER ---- ----- ----- -------------------------------------------------------------------- --- .... ............. 1631 ANATABINE, N-FORNYL- 188 61892-65-7 872 ANATABINE, N-IETHYL- (SL30D) 174 S953-S1-5 499 ANATABINE (BIPYRiDINE-2,31, 1,2,3,6-TETRAHYDRO-,(S)) 160 581-49-7 1370 ANATABiNE (isomer) 160 1257 ANILiNE, 2,4-DINETNYL- 121 95-68-1 1834 51.4 ANILiNE, 2-NETHONY-5-METHYL- 137 S08b8-72-9 483 2-METHYL- (2-AMINOTOLUENE) ANILINE 107 §5-53-4 1258 , ANILINE, N,N-DINETHYL- 121 121-69-7 482 ANILINE, N-ETHYL- 121 103-69-5 1263 ANILINE, N-PHENYL- (BEN2ENEANINE, N-PHENYL-) 169 122-39-4 1256 ANILINE (BEN2ENAMINE) 93 62-53-3 1262 ANILINE, ?-BENZYL- 183 28059-64-5 1261 , ANILINE, ?-(?-NETHYLPHENYL)- 183 91 19.3 ANISOLE, (BENZENE METHONY-) 108 100-66-3 1799 75.1 ANTHRACENE 178 120-12-7 969 AZAFLUORENE-4 (SBB2170) 167 1128 AZETIDINE 57 503-29-7 57 28.1 56.8 BENZALDEHYDE 106 100-52-7 1395 BENZALDEHYDE, 2,3-DINETHOXY- 166 86-51-1 1394 BENZALDEHYDE, 2,4-DINETHORY- 166 613-45-6 1399 BENZALDEHYDE, 2-HYDRONY- 122 90-02-8 1405 31.9 66.0 BENZALDEHYDE, 2-NETHYL- (o-TOLUALDENYDE) 120 529-20-4 1860 63.8 BENZALDEHYDE, 3,4-DINETHONY- (VERATRALDENYDE) 166 120-14-9 1396 BENZALDEHYDE, 3,5-DINETNOD(Y- 166 7311-34-4 1401 BENZALDEHYDE, 3-NYDROD(Y- 122 100-83-4 1404 BEN2ALDEHYDE, 3-NETHONY- 136 591-31-1 1406 32.5 65.8 BENZALDEHYDE, 3-METHYL- (arTOLIIALDEHYDE) 120 620-23-5 2136 69.6 100.2 BENZALDEHYDE, 4,6-DIHETHODfY-2-HYDROD(Y- 182 1397 BENZALDEHYDE, 4-ETHYL- 134 4748-78-1 1400 89.8 BENZALDEHYDE, 4-HYDRONY- 122 123-08-0 1402 BENZALDEHYDE, 4-HYDRONY-3,5-DINETHONY- (SYRINGALDEHYDE) 182 134-96-3 1857 88.7 BENZALDEHYDE, 4-NYDRODQf-3,5-DINETNOIQf- (SYRINGALDENYDE) 182 134-96-3 2140 69.2 91.4 BENZALDEHYDE, 4-HYDRO7(Y-3-ETHOD(Y- (VANILLIN, ETHYL-) 166 121-32-4 1398 69.2 91.4 BENZALDEHYDE, 4-HYDRODfY-3-ETHOD(Y- (VANILLIN, ETHYL-) 166 121-32-4 51 70.4 BENZALDEHYDE, 4-HYDR00(Y-3-NETN00(Y- (VANILLIN) 152 121-33-5 1403 50.5 BENZALDEHYDE, 4-NETHOD(Y- (p-ANISALDEHYDE) 136 123-11-5 1780 33.1 66.9 BENZALDEHYDE, 4-METHYL- 120 104-87-0 1407 33.6 66.9 BENZALDEHYDE, 4-METHYL- (p-TOLWILDENYDE) 120 104-87-0 1408 BENZALDEHYDE, 4-(1-NETHYLETHYL) (C{R/IC ALDEHYDE) 148 122-03-2 1810 67.6 BENZALDEHYDE, 4-(DINETHYLANINO)- 149 100-10-7 1809 67.6 BENZALDEHYDE, 4-(DINETHYLANINO)- 149 100-10-7 181 75.2 BENZANIDE 121 55-21-0 1260 BEN2ENANINE, 3-METHYL- (ANILINE, 3-METHYL-) 107 108-44-1 2009 29.7 BENZENE 78 71-43-2 1206 49.5 BENZENE, 1,11-OXYBIS- (DIPHENYLETHER) 170 101-84-8 1204 50.0 BENZENE, 1,11-OXYBIS[4-METHYL-DI• (4-METHYLPHENYLETNER) 198 1579-40-4 1695 63.7 BENZENE, 1,11-[OD(YBIS(NETHYLENE))BIS (DIBENZYL ETHER) 198 103-50-4 1205 48.3 BENZENE, 1,2,3-TRIMETNOD(tt- 168 634-36-6 223 18.6 63.9 BENZENE, 1,2,3-TRIMETHYL- 94 S26-73-8 1986 16.0 60.9 BENZENE, 1,2,4-TRIMETHYL- 120 95-63-6 1193 BENZENE, 1,2-DIHETH00(Y- 138 91-16-7 122 BENZENE, 1,2-DINETHOJ(Y- (VERATROLE) 138 91-16-7 1196 BENZENE, 1,2-DINETHOI(Y-4-ETHENYL- 164 6380-23-0 1195 BENZENE, 1,2-DINETHONY-4-NETHYL- 152 494-99-S 166 BENZENE, 1,2-DINETHOXY-4-(2-PROPENYL)- (EU6ENOL, NETHYL-) 180 93-15-2 231 52.9 BENZENE, 1,2-DINETNYL- (0-XYLENE) 106 95•47-6 1062 BENZENE, 1,2-EPOXYETHYL- (STYRENE OXIDE; PHENYLOXIRANE) 120 96-09-3 2014 14.3 58.7 BENZENE, 1,3,5-TRINETHYL- 120 108-67-8 1970 50.7 BENZENE, 1,3-DINETHYL- 106 108-38-3 1194 BENZENE, 1,4-DINETHOD(Y- 138 1S0-78-7 1192 BENZENE, 1,4-DINETHOD(Y-2-(1-NETNYLETHYL)-5-METHYL- (NY194) 194 14753-08-3 1943 10.0 50.0 BENZENE, 1,4-DINETHYL- 106 106-42-3 2043 19.7 60.6 BENZENE, 1-ETHENYL-3-HETHYL- (STYRENE, 3-NETHYL-) 118 100-80-1 1979 15.1 59.7 BENZENE, 1-ETHYL-2-NETHYL- 120 611-14-3 2025 13.6 58.0 BENZENE, 1-ETHYL-3-NETHYL- 120 620-14-4 1990 13.5 59.2 BENZENE, 1-ETHYL-4-NETHYL- 120 622-96-8 1198 BENZENE, 1-METH00(1f-2-NETBYL- (ANISOLE, 2-METHYL-) 122 578-58-5 1203 BENZENE, 1-NETHOXY-4(2-PROPENYL)- 148 140-67-0 ' 1202 BENZENE, 1-NETHOXY-4(2-PROPENYU- 148 140-67-0 ' 1197 BENZENE, 1-NETHOXY-4-ETHENYL- 134 637-69-4 1199 BENZENE, 1-NETHORY-4-NETHYL- (ANISOLE, 4-NETHYL-) 122 104-93-8 20

TOBACCO.WKI Retention Time Database - Septeaber S, 1989 RT (min) CMPD ----------- A DBWAX DB1 Sorted by Caffpoud Name CONPOUIiD NAME ----------------------------------------------------------------------- MY CAS NUlBER 168 43.0 81.6 BENZENE, 1-METHOXY-4-(1-PROPENYL)- (ANETHOL) 148 104-46-1 2093 11.4 54.8 BENZENE, 1-METHYLETHYL- 120 98-82-8 1201 BENZENE, 1-(1-METHYLETHYL)-3-METHONY-4-NETHYL- 164 6379-73-3 226 15.6 BENZENE, 1-(i-METHYLETHYL)-4-METNYL- (CYMENE-p) 134 99-87-6 1200 BENZENE, 2-METHOXY-1-IETHYL-4-PROPENYL- 162 40793-85-9 2047 15.3 56.5 BENZENE, 2-PROPENYL- 118 300-57-2 2024 15.3 56.5 BENZENE, 2-PROPENYL- 118 300-57-2 1099 BENZENE, 5-(2-PROPENYL)-1,2,3-TRIMETHOXY- 208 487-11-6 2003 28.9 69.3 BENZENE, DIMETHOXYNETHYL- 152 1125-88-8 172 14.9 51.7 BENZENE, ETHENYL- (STYRE NE) 104 100-42-5 2061 24.7 69.1 BENZENE, ETHENYL-2,4-DIIE THYL- (STYRENE, 2,4-D1IETHYL-) 132 2234-20-0 2060 24.3 68.8 BENZENE. ETHENYL-2,5-DINE THYL- (STYRENE, 2,5,-DIMETHYL-) 132 2039-89-6 2051 19.8 61.0 BENZENE, ETHENYL-4-METHYL- (STYRENE, 4-METHYL-) 118 622-97-9 232 9.8 49.2 BENZENE, ETHYL- 106 100-41-4 2030 20.6 50.4 BENZENE, ETHYNYL- 102 536-74-3 220 6.4 40.8 BENZENE, METHYL- (TOLUEN E) 92 108-88-3 222 BENZENE, PROPYL- 120 103-65-1 1929 BENZENEACETONITRILE 117 140-29-4 385 46.0 69.7 BENZENEACETONITRILE 117 140-29-4 1484 BENZENEACETONITRILE, 4-HY DROXY- 133 14191-95-8 1259 BENZENEAMINE, 4-METHYL- (ANILINE, 4-METHYL-) 107 106-49-0 485 BENZENEANINE, N-PHENYL- (ANILINE, N-PHENYL-) 169 122-39-4 1924 71.5 BEN2ENEDIAMINE-1,3, 2-METHYL- 122 823-40-5 1923 71.5 BENZENEDIAMINE-1,3, 2-METNYL- 122 823-40-5 1920 66.7 BENZENEDIAMINE-1,4 (PHENYLENEDIANINE-1,4) 108 106-50-3 1485 65.0 81.6 BENZENEDICARBONITRILE-1,2 128 91-15-6 1486 60.3 76.9 BENZENEDICARBONITRILE-1,3 128 626-17-5 1487 76.1 BENZENEDICARBONiTRILE-1,4 128 623-26-7 1823 80.4 BENZENEMETHANOL, 4-HYDR00(Y-3-METHOHY- (VANILLYL ALCOHOL) 154 498-00-0 725 BENZENEMETHANOL, 4-NETH00(Y-, ACETATE (ANISYL ACETATE) 180 104-21-2 1667 60.5 BENZENEMETHANOL, 4-METHONY- (BENZYL ALCOHOL 4-METN00(Y-) 138 105-13-5 1501 43.3 BENZENEMETHANOL, a,a,4-TRIMETNYL- (CYMENOL-6) 1S0 1197-01-9 1839 42.0 BENZENEMETHANOL, a-METHYL- 122 98-85-1 1563 42.1 BENZENEMETHANOL, a-METHYL- 122 98-85-1 56 44.8 BENZENEMETHANOL (BENZYL ALCOHOL) 108 100-51-6 1835 78.0 BENZENE-1,2-DIOL, 4-METHYL- (CATECHOL, 4-METHYL-) 124 452-86-8 97 74.9 BENZENE-1,2-DIOL (CATECHOL) 110 120-80-9 2160 74.9 BENZENE-1,2-DIOL (CATECHOL) 110 120-80-9 949 BENZENE-1,4-D10L, METHYL- (METHYLHYDROOUINOME) 124 95-71-6 739 BENZENE-1,4-DIOL, mono-ACETATE (HYDROOUINONE, mono-ACETATE) (PHENOL , 4-ACETO 152 -3233-32-7 948 86.6 78.3 BENZENE-1,4-DIOL (HYDROQUINONE) 110 123-31-9 1579 63.0 BENZIDANE-1,3-DIONE, 2,2-DIETHYL-4,7-DIMETHYL- 230 614 68.5 BENZiMIDAZOLE-1H 118 51-17-2 95 68.5 BENZiMIDAZOLE-1H 118 51-17-2 307 69.8 BENZINIDAZOLE-IH, 1,2-DINETHYL- (SW160D) 146 2876-08-6 1181 BENZIMIDAZOLE-1H, 1-ETNYL- 146 7035-68-9 1871 132.5 BENZINIDAZOLE-IH, 2,5,6,-TRIMETNYL- 160 3363-56-2 311 BENZINIDAZOLE-IH, 2-BUTYL- (SW146D) 174 5851-44-5 1180 BENZIM1DA20LE-1H, 2-ETHYL- 146 1848-84-6 1183 99.6 BENZINIDAZOLE-IH, 2-METHYL- 132 615-15-6 312 BENZINIDAZOLE-IH, 2-PENTYL-, (SYN) 188 5851-46-7 615 BENZIMIDAZOLE-1H, 2-(2-ETHYLPHENYLMETHYL)- (SW163D) 236 313 BENZIMIDAZOLE-1H, 2-(2-NAPHTNALENYLNETHYU- (SW149D) 258 82326-40-7 308 BENZINIDAZOLE-IH, 2-(3-METHYLBUTYL)- (SWWIS4D) 188 946-18-9 1232 BENZIMIDAZOLE-1H, 2-(4-THIAZOLYL)- 201 148-79-8 1182 BENZIMIDAZOLE-1H, 5,6-DIMETHYL- 146 S82-60-5 909 BENZINIDAZOLE-IH, C2-ALKYL- (SW59D) 146 908 BENZINIDAZOLE-IH, C2-ALKYL- (SSIW61D) 146 1884 57.0 BENZINEAMINE, 3-METHOD(Y- (ANILINE, wetha-METHOXY; m-ANISIDINE) 123 536-90-3 1188 BENZODIAZINE-1,2 (CINNOLINE, 4-METNYL-) 144 14722-38-4 619 BENZODIAZINE-1,2 (CINNOLINE, 4-METNYL-) 144 14722-38-4 1187 BENZODIAZINE-1,2 (CINNOLINE) 130 253-66-7 1843 43.9 BENZODIOXIDE-1,3, 5-PROPYL- (SAFROLE) 162 94-59-7 1157 43.9 BENZODIOXOLE-1,3, 5-(2-PROPENYL)- (SAFROLE) 162 94-59-7 1160 BENZOFURAN, 2,3-DIHYDRO- 120 496-16-2 1209 BENZOFURAN, 2,3-DIHYDR0-2-METHYL- 134 1746-11-8 1210 BEN20FURAN, 2,3-DIMETHYL- 146 3782-00-1 1211 BENZOFINtAN, 2-ETHYL- 146 3131-63-3 2048 31.1 69.9 BENZOFURAN, 2-METHYL- 132 4265-25-2 1213 BENZOFURAN, 2-METHYL- 132 4265-25-2 1215 BENZOFURAN, 3,6-DINETHYL-4,5,6,7-TETRANYDRO- 1S0 494-90-6 21

TOBACCO.WK1 Retention Time Database - September 5, 1989 CMPD RT (min) # DBWAX DB1 441 1212 1214 1502 77.0 1505 54.3 1490 55.5 1707 52.3 691 628 26.8 61.0 29 65.5 72.2 1537 39.8 1844 78.5 113 645 90.5 646 92.0 647 1543 35.1 1544 33.0 233 31.5 58.3 2096 38.2 73.6 1488 2095 33.6 65.6 2094 35.4 67.1 1596 384 37.2 68.1 1592 1593 1594 1595 25 1489 43.2 1233 92 34.3 1185 1184 1186 35.6 616 617 618 1411 58.4 688 60.1 500 1859 72.3 2142 83.9 47 1510 28.1 197 1805 31.3 1831 35.3 1540 12.8 1897 42.8 1747 57.8 1678 66.7 1804 37.1 1807 10.7 1803 48.7 11 66.9 962 58.2 501 963 318 270 636 638 637 642 299 502 271 639 641 Sorted by Cawpotnd Name COMP0lN1D NAME MW CAS NUNBER ----------------------------------------------------- --- -- ---------- - - BENZOFURAN, 3-ACETYL- 160 66611-15-2 BENZOFURAN, 3-ETHYL- 146 36724-24-0 BENZOFURAN, 3-METHYL- 132 21535-97-7 BENZOFURAN, 6,7-DIMETHYL-5-HYDROXY- 162 60026-12-2 BENZOFURAN, 6,7-DIMETHYL-5-METHOHY- 176 35355-35-2 BENZOFURANCARBOXALDEHYDE-2 146 4265-16-1 BENZOFURANONE-2(3H), NEXANYDRO- 140 6051-03-2 BENZOFURANONE-2(3H), NEl(ANYDR0-4-8YDROD(Y- BENZOFURAN-2,3 BENZOIC ACID BENZOIC ACID, BENZOIC ACID, BENZOIC ACID, BENZOIC ACID, BENZOIC ACID, BENZOIC ACID, BENZOIC ACID, BENZOIC ACID, BENZONITRILE BENZONITRILE, BENZONITRILE, BENZONITRILE, BENZONITRILE, BENZONITRILE, BENZONITRILE, BENZONITRILE, BENZONITRILE, BENZONITRILE, (3-CYCLOHEXANEACETIC ACID, 1,2-DIH 156 54911-63-6 2-HYDROHY-, METNYL ESTER (SALICYLIC ACID,METHYL ESTER) 2-HYDROXY- (SALICYLIC ACID) 2-METHYL- (TOLUIC ACID) 3-HYDROD(Y- 4-HYDRONY- 4-HYDROXY-3-METNOXY- ETHYL ESTER METHYL ESTER (VANILLIC ACID) 2,5-DINETHYL- 2-AMINO- 2-METHYL- 3-METNYL- 4-HYDROD(Y- 4-METNYL- C2-ALKYL-, (1) C2-ALKYL-, (2) C2-ALKYL-, (3) BENZONITRILE, C2-ALKYL-, (4) BENZOPYRAN-1(5H), 2,3,6,7,8,8a-HEXIIHYDR0-7-OXO-2,5,5,8a-TETRAMETHYL- BENZOGUINONE, TETRAMETHYL- BENZOTHIAZOLE-1H BENZOXAZOLE BENZOXAZOLE, 2,4-DINETHYL- BENZOHAZOLE, 2,5-DINETHYL- (SNN84D) BENZOHAZOLE, 2-METHYL- BENZOxAZOLE, 4,6(or5,7)-DIMETHYL- (SB8164D) BENZOHAZOLE, 7-ETHYL- (SBBISBD) BENZOXAZOLE, C3-ALKYL- (SBB1530) BENZO-1,3-DIOXOLE-5-CARBOOfALDENYDE (HELIOTROPIN) BENZO-2H-I-PYRAN-2-ONE, 3,4-DINYDRO- (COUMARIN, 3,4-DINYDRO-) BENZO[F]GUINOLINE BENZYL ALCOHOL, 3,4-DIMETHOXY- BENZYL ALCOHOL, 4-HYDROXY- BENZYL BENZOATE BENZYL PROPYL ETHER BICYCLO(2.2.1.)HEPTEN-2-ONE, 1,7,7-TRIMETNYL- (D-CAMPHOR) 118 122 152 138 136 138 138 168 150 136 103 131 118 117 117 119 117 131 131 131 131 208 271-89-6 65-85-0 119-36-8 69-72-7 118-90-1 99-06-9 99-96-7 121-34-6 93-89-0 93-58-3 100-47-0 13730-09-1 1885-29-6 529-19-1 620-22-4 767-00-0 104-85-8 164 527-17-3 135 95-14-7 119 273-53-0 147 72692-90-1 147 5676-S8-4 133 95-21-6 147 72692-91-2 147 78210-57-8 147 150 148 179 168 124 212 1S0 152 BICYCLO[2.2.1]HEPAN-2-OL, 1,7,7-TRIMETHYL-,IS-ENDO, ACETATE (BORNEOL ACETATE 196 BICYCLO[2.2.1]HEPTAN-2-0L, 1,7,7-TRIMETNYL-, EXO- (BORNEOL-iso) 154 BICYCLO[2.2.2]OCTANE, 1,3,3-TRIMETHYL-2-ONA- (CINEOLE-1,8) BICYCLO[321]OCTAN, 7,8-DIOXA-1-ME-4-(1-METNYLETHYL)-6-OH0- (SR113C) BICYCLO[440]DECANE, 9-HYDROXY-10-ODOD-1,5,5,9-TETRAMETNYL- BICYCLO[440]DECA-1,9-DIENE-3-ONE, 5,5,9-TRIMETHYL- BICYO[2.2.1]HEPTAN-2-OL, 1,7,7-TRIMETNYL-,IS-ENDO (BORNEOL) BICYO(4.1.0.]HEPT-3-ENE, 3,7,7-TRIIETHYL- (CARENE, delta-3) BIPHENYL BIPYRIDINE BIPYRIDINE-2,2' BIPYRIDINE-2,21, 4-METHYL- (SBB185D) BIPYRIDINE-2,31, 1-METNYL-1,2,3,4-TETRAHYDRO- BIPYRIDINE-2,3', 3-ETHYL- (SWW133D) BIPYRIDINE-2,31, 3-METHYL-OR 6-METHYL- (SYU108D) BIPYRIDINE-2,31, 4-PROPYL- (SIIU135D) BIPYRIDINE-2,31, 4-(2-BUTENYL)- B1PYR1DINE-2,31, 4-(2-PROPENYL)- (S{N136D) BIPYRIDINE-2,31, 5-ETHENYL- (SW168D) BIPYRIDINE-2,31, S-ETHYL- (SWU109D) BIPYRIDINE-2,31, 5-METHYL- (SR107D) BIPYRIDINE-2,31, S-METHYL- (SR107D) BIPYRIDINE-2,31, 5-(1-PROPENYL)- (SW11150D) BIPYRIDINE-2,31, 6-ETHYL- (SW159D) 154 184 120-57-0 119-84-6 85-02-9 93-03-8 623-05-2 120-51-4 937-61-1 76-22-2 5655-61-8 124-76-5 470-82-6 224 190 583S-19-8 154 464-45-9 136 13466-78-9 154 92-52-4 156 37275-48-2 156 366-18-7 170 56100-19-7 174 5953-51-5 184 78210-76-1 170 26636-59-9 or 198 210 78210-75-0 196 78210-74-9 182 78210-81-8 184 34671-89-1 170 26844-80-4 170 26844-80-4 196 78210-79-4 184 78210-77-2 78210 Ln N m N m W 0D 22 m ~

. TOBACCO.WIC1 Retention Time Database - September 5, 1989 Sorted by Ccmpousd Name RT (min) CNPD * DBWAX DB1 COMPOl1ND NANE MW CAS NUMBER ---- 966 ----- ----- --------------------------------------------------- ----- ---------- BIPYRIDINE-2,3', 6-HYDROD(Y-3,4,5,6-TETRAHYDRO- 176 ............. 354 BIPYRIDINE-2 3 6-METHYL- (OR 3-NETHYL- CAS#26636-59-9) (SYW201D) 170 78210-78-3 640 BIPYRIDINE-2,3', 6-PROPIONYL-(?) (SW151D) 212 415 BIPYRIDINE-2,3', 7-ETHYL- (SiN232D) 184 1763 67.7 BIPYRIDINE-2,4' 156 581-47-5 876 68.3 BIPYRIDINE-3,3' 156 581-46-4 350 BIPYRIDINE-3,3', 5-METHYL- (SW197D) 170 78210-82-9 503 BIPYRIDINE-3,3', 6-NETHYL- (SBB191D) 170 78210-83-0 965 68.7 96.8 BIPYRIDINE-4,4' 170 553-26-4 325 BIYPRIDINE-2,2', 4,5-DINETHYL- (SW 173D) 184 78210-73-8 65 73.0 BOVOLIDE, SPIRO- (ISOMER R.T76.30) (SR56C) 196 41059-94-3 1412 2.9 21.0 BUTANAL 72 123-72-8 1414 BUTANAL, 3-HYDRODfY- (ALDOL) 88 107-89-1 1416 3.4 27.6 BUTANAL, 3-METHYL- (ISOVALERALDEHYDE) 86 590-86-3 371 BUTANANIDE, 3-METHYL- (ISOVALERANIDE) 101 541-46-8 1264 BUTANANINE, N-METHYL- 87 110-68-9 1271 6.1 26.3 BUTANANINE-1 73 109-73-9 1265 BUTANANINE-1, 3-METHYL- 87 107-85-7 1267 BUTANAMINE-1, N-BUTYL- 129 111-92-2 1266 BUTANANINE-1, N-METNYL-N-NITROSO- 116 7068-83-9 1273 BUTANANINE-1, N-PROPYL- 115 20193-21-9 1268 21.0 BUTANAMINE-2 73 13952-86-6 1269 BUTANANINE-2, N-(1-NETHYLPROPYL)- 129 626-23-3 733 BUTANDIOIC ACID, HYDROXY-, DIMETHYL ESTER 162 1587-15-1 1234 BUTANE, 1-NETHYLTNIO- 104 628-29-5 1235 BUTANE, 1-PROPYLTHIO- 132 1613-46-3 1326 BUTANEDIAMIDE (SUCCINAMIDE) 116 110-14-5 947 BUTANEDINITRILE (SUCCINONITRILE) 80 110-61-2 666 BUTANEDIOIC ACID, MONO METHYL ESTER (SUCCINIC ACID, Mono-METHYL ESTER) 132 3878-SS-S 1712 63.5 BUTANEDIOIC ACID, MONO METHYL ESTER (SUCCINIC ACID, mon-METHYL ESTER) 132 3878-55-5 1988 8.6 28.2 BUTANENITRILE 69 109-74-0 2168 7.7 33.8 BUTANENITRILE, 2-METHYL- 83 2SS70-03-0 393 9.4 BUTANENITRILE, 3-METHYL- 83 625-28-5 1236 BUTANETHIOL-1 (BUTYL MERCAPTIN) 90 109-79-5 1237 BUTANETHIOL-2 90 513-53-1 2008 24.9 BUTANE-1,3-DIENE, 2,3-DIlNETHYL- 82 513-81-5 1991 BUTANE-2,3-DIONE 86 431-03-8 34 BUTANOIC ACID 88 107-92-6 1535 BUTANOIC ACID 88 107-92-6 1882 43.8 BUTANOIC ACID, PNENYLNETHYL ESTER 178 103-37-7 1607 22.6 BUTANOIC ACID, 2,2-DINETHYL-3-OXO-, ETHYL ESTER 158 597-04-6 153 BUTANOIC ACID, 2-ETHYL- 116 88-09-5 652 BUTANOIC ACID, 2-HYDROXY- 104 565-70-8 2037 36.0 46.2 BUTANOIC ACID, 2-METHYL- 102 600-07-7 35 36.0 46.2 BUTANOIC ACID, 2-METHYL- 102 600-07-7 1864 43.6 BUTANOIC ACID, 3-METHYL-, 4-OXOPENTYL ESTER 186 112 BUTANOIC ACID, 3-METHYL- (ISOVALERIC ACID) 102 503-74-2 2066 22.6 47.1 BlJTANOIC ACID, 3-OXO-, METHYL ESTER (ACETOACETIC ACID, NETHYL ESTER) 116 105-45-3 2197 18.7 BUTANOIC ACID, ANYL ESTER (AMYL BUTYRATE) 158 2198 16.0 BUTANOIC ACID, ISOANYL ESTER (1SOAMYL BUTYRATE) 158 1597 10.9 28.3 BUTANOL-1 74 71-36-3 2072 12.9 36.4 BUTANOI-1, 2 METHYL- 88 137-32-6 1940 18.4 46.1 BUTANOL-1, 2-ETHYL- 102 97-95-0 1500 13.4 BUTANOL-1, 3-NETHYL- (ISOANYL ALCOHOL) 88 123-51-3 2082 26.4 BUTANOL-2, 2-METHYL- 88 75-85-4 2071 30.7 BUTANOL-2, 3-METHYL- 88 598-75-4 2070 22.2 BUTANOL-2(+/-) 74 1S892-23-6 803 BUTANONE-1, 1-PYRA2INYL- (SR236D) 150 61892-81-7 306 BUTANONE-1, 1-(3-PYRIDINYL)- (SWN106D) 149 1701-70-8 333 BUTANONE-1, 2-NETHYL-1-(3-PYRIDINYL)- (SW 170D) 163 78210-70-5 1469 BUTANONE-1, 4-(NETHYLNITROSOANINO)-1-(3-PYRIDINYL)- 207 64091-91-4 1967 3.2 20.6 BUTANONE-2 72 78-93-3 2187 21.0 BUTANONE-2, 1-HYDROXY- 88 5077-67-8 1721 32.1 BUTANONE-2, 3,3-DINETHYL-4-HYDROXY- 116 38895-88-4 1743 16.3 31.7 BUTANONE-2, 3-HYDROXY- 88 513-86-0 1963 27.6 BUTANONE-2, 3-METHYL- 86 563-80-4 2154 32.4 BUTANONE-2, 4-ACETOXY- 130 10150-87-5 1638 31.8 56.6 BUTANONE-2, 4-ACETYLOXY- (BUTAN-2-ONE 4-HYDROXY-, ACETATE) 130 10150-87-5 726 BUTANONE-2, 4-HYDROXY-, ACETATE (BUTAN-2-ONE, 4-ACETYLOXY-) 130 10150-87-5 804 17 4 BUTANONE-2 4-HYDROXY- (SR2350) 88 590-90-9 1840 . 92.8 , BUTANONE-2, 4-(4-HYDROXYPHENYL)- (OXANONE) 164 5471-51-2 23

TOBACCO.WK1 Retention Time Database - September 5, 1989 Sorted by Compound Name RT (min) CNPD ----------- * DBWAX DB1 COMPOUND NANE NW CAS NUIBER ---- ----- ----- ----------------------------------------------------------------------- ---- ------------- 838 BUTAN-1,2,3-TR10L 106 4435-50-1 1609 43.9 BUTAN-1,2-DIONE, 1-(2-FURYU - (SR183C) 152 1438-90-0 1752 40.1 47.2 BUTAN-1,3-DIOL 90 107-88-0 1270 BUTAN-1,4-DIAMINE 88 110-60-1 837 30.5 39.6 BUTAN-2,3-DIOL 90 513-85-9 442 4.7 19.9 BUTAN-2,3-D10NE (DIACETYL) 86 431-03-8 2108 1.7 18.1 BUTA-1,3-DIENE, 2-METHYL- (ISOPRENE) 68 78-79-5 1418 BUTENAL-2, 2-METHYL- (CROTOHALDEHYDE, 2-NETHYL-) 84 1115-11-3 1419 BUTENAL-2, 3-METHYL- (CROTONALDEHYDE, 3-METHYL-) 84 107-86-8 1417 26.4 BUTENAL-2 (CROTONALDEHYDE) 70 4170-30 3 2028 7.8 25.2 BUTENENITRILE-2 (CROTONONITRILE cis & trans) 67 4786-20-3 2029 10.2 28.3 BUTENENITRILE-2 (CROTONONITRILE trans or cis) 67 1190-76-7 2039 1.5 19.7 BUTENE-1, 2,3-DINETHYL- 84 563-78-0 2056 1.5 14.4 BUTENE-1, 3,3-DIMETHYL- 84 558-37-2 1976 26.5 BUTENE-2, 2,3-DINETHYL- 84 563-79-1 215 BUTENOIC ACID-2, 2-METHYL- 100 13201-46-2 649 BUTENOIC ACID-2, 3-METHYL- (SENECIOIC ACID) 100 541-47-9 648 40.2 BUTENOIC ACID-2 (CROTONIC ACID) 86 107-93-7 650 BUTENOIC ACID-3 86 625-38-7 651 BUTENOIC ACID-3, 3-METHYL- 100 1617-31-8 1683 64.3 BUTEN-3-ONE-2, 4-(1-HYDROI(Y-2,2-DINETHYL-6-METHYLENECYCLOHEXYL)- 208 15356-75-9 840 BUTYL ALCOHOL, 2-METHYL-4-PYRA2INYL- (SR207D) 166 61892-91-9 1413 5.6 BUTYRALDEHYDE, 2-ETHYL- 100 97-96-1 1415 3.4 28.2 BUTYRALDEHYDE, 2-METHYL- 86 96-17-3 368 46.4 54.2 BUTYRAMIDE 87 541-35-5 1325 BUTYRAMIDE, 2,3-DINETHYL- 115 66309-91-9 369 46.5 BUTYRAMIDE, 2-NETHYL- 101 1113-57-1 1565 46.2 BUTYRAMIDE, 2-METHYL- 101 1113-57-1 1324 BUTYRAMIDE, 3-CYANO-3-METHYL- (SR183D) 126 61892-66-8 754 BUTYRANIDE, 4-CYANO- (SWW64D) 112 53897-27-1 178 46.8 BUT-2-ENAL, 2-PHENYL- (CROTOMALDEHYDE, 2-PHENYL-) (SWW98D) 146 5S088-52-3 274 46.8 BUT-2-ENAL, 2-PHENYL- (CROTOMALDEHYDE, 2-PHENYL-) (SWW98D) 146 5S088-52-3 752 BUT-2-ENANiDE 85 23350-58-5 751 47.6 BUT-2-ENANIDE, 2-METHYL- 99 32793-37-6 1327 51.6 BUT-2-ENANIDE, 3-METHYL- 99 4479-75-8 1642 46.2 BUT-2-ENAMIDE, N,2-DINETHYL- 113 1187-41-3 158 42.1 BUT-2-EN-I-ONE, 1-(2,6,6-TRINETHYL-1,3-CYCLOHEXADIEN-1-YL)- (DAMASCENONE) 190 23696-85-7 157 42.1 BUT-2-EN-I-ONE, 1-(2,6,6-TRIMETHYL-1,3-CYCLOHEXADIEN-1-YL- (DAMASCENONE) 190 23696-85-7 1555 42.2 BUT-2-EN-l-ONE, 1-(2,6,6-TRINETHYL-I-CYCLOHEXEN-1-YL)- (DANASnONE-bete) 192 35044-68-9 49 BUT-2-EN-I-ONE, 1-(2,6,6-TRIMETHYL-I-CYCLOHEXEN-1-YL)- (DAMASCONE-beta) 192 35044-68-9 1620 69.6 BUT-2-EN-l-ONE, 1-(3-HYDROXY-2,6,6,-TRINETHYL-1-CYCLOHEXEN-1-YL)- (DAMASCONE 208 102488-09-5 19 69.0 BUT-2-EN-I-ONE, 1-(4-ON-2,6,6-TRINe-1-CYCLOHEXEN-I-YU- (DAMASCONE-b,4-OH-) 208 56915-02-7 753 BUT-3-ENAMIDE 85 28446-58-4 2053 11.7 25.9 BUT-3-ENENITRILE (ALLYL CYANIDE) 67 109-75-1 1982 25.7 BUT-3-ENENITRILE (ALLYL CYANIDE) 67 109-75-1 839 BUT-3-EN-1,2-DIOL (S'i1W8D) 88 497-06-3 1272 BUT-3-EN-1-MINE, N-NETHYL-4-(3-PYRIDINYL)- 162 538-79-4 1692 12.0 BUT-3-EN-1-OL 72 627-27-0 2063 20.0 BUT-3-EN-2-ONE 70 78-94-4 1574 54.2 BUT-3-EN-2-ONE, 4-PHENYL- 146 122-57-6 277 45.9 BUT-3-EN-2-ONE, 4-(2-FURYL)- (SWWD40) 136 625-15-4 334 BUT-3-EN-2-ONE, 4-(2-FtIRYL)-3-NETHYL- (SWW92D) 136 81540-27-4 805 BUT-3-EN-2-ONE, 4-(4-HYDROXY-1-CYCLOHE)(EN-I-YL)- (SR129D) 166 61892-82-8 279 BUT-3-EN-2-ONE, 4-(5-METHYL-2-FLMtYL)- (SWN96D) 1S0 23120-57-2 925 91.2 CAFFEINE 194 58-08-2 1547 27.7 CAMPHOR-D 152 464-49-3 1050 CARBAZOLE-9H, 1-METHYL- 181 6510-65-2 1049 CARBAZOLE-9H, 2-METHYL- 181 3652-91-3 1048 3-METHYL- 181 CARBA20LE-9H 4630-20-0 1047 , CARBAZOLE-9H, 4-METHYL- 181 3770-48-7 1046 CARBA20LE-9H, (H.W.167) 167 86-74-8 2149 1.4 3.3 CARBON DIOXIDE 44 124-38-9 1815 48.7 CARYOPHYLLENE OXIDE 220 1139-30-6 1534 54.3 CEDRYL PROPYL ETHER 236 19870-75-8 185 54.3 CEDRYL PROPYL ETHER 264 19870-75-8 2145 5.8 24.8 CHLOROFORM 120 67-66-3 67 CHROMANONE-7, OCTAHYDRO-2,5,5,8a-TETRAMETHYL- (SR26C) 210 S835-18-7 320 CHROMONE, 2-ETHYL- (SW1290) 174 828-82-0 1605 59.1 CINNANYL-para-NETHOXY METHYL ETHER 178 12 84.0 COTININE 176 486-56-6 689 69.6 COLPlIARIN, 6-METHYL- 160 92-48-8 24

TOBACCO.WK1 Retention Time Databsse - September 5, 1989 Sorted by Ccspound Name RT (min) CMPD ----------- S DBWAX DB1 COMPOUND NAME N.W CAS NINIBER ---- ----- ----- ----------------------------------------------------------------------- .... ............. 690 1861 65.4 COIJlIARIN, 7-HYDROHY-6-NETH00(Y- (SCOPOLETIN) 192 92-61-5 146 91-64.-5 COLOIARiN (BEN20PYRAN-2-ONE-2H-1) 210 CROTONAMIDE, 2-METNYL- 99 32793-37-6 1702 47.8 CROTONAMIDE, N-ETNYL- 113 233S0-60-9 2183 3.3 CYCLOHEXADIENE,1-4- 80 628-41-1 2195 2.7 30.7 CYCLONEXADIENE-1,3 80 S92-S7-4 2010 61.9 CYCLOHEXANE, 1,1-DIHETH00(Y- 144 933-40-4 2011 65.6 CYCLOHEXANE, 1,1-DINETHONY-3-NETHYL- 158 18349-16-1 2002 16.0 66.4 CYCLOHEXANE, 1,1-DINETNODQf-4-NETNYL- 158 18349-20-7 2035 17.3 CYCLOHEXANE, 1,1-DINETNOHY-4-IETHYL- 158 18349-20-7 2033 66.4 CYCLOHEXANE, 1,1-DIMETHOD(Y-4-NETNYL- 60 18349-20-7 1932 2.9 47.3 CYCLOHEXANE, 1,2-DINETHYL-cis, (for trans see 1931) 112 Z207-01-4 1931 2.5 44.3 CYCLOHEXANE, 1,2-DIMETHYL-trans, (for cis see 1932) 112 6876-23-9 1936 2.2 42.4 CYCLOHEXANE, 1,4-DINETHYL-cis, (for trans see 1937) 112 624-29-3 1937 2.3 44.9 CYCLOHEXANE, 1,4-DIMETHYL-trans, (for cis sea 1936) 112 Z207-04-7 1933 2.1 36.6 CYCLOHEXANE, METHYL- 98 108-87-2 692 CYCLOHEXANECARBOD(YLIC ACID, 2,3-DINYDRONY-3-NETNYL-, LACTONE (SR180D) 156 1589 54.1 CYCLOHEXANEIR_TNANOL, 4-NYDROD(Y-a,a,4-TRIMETNYL- (TERPIN HYDRATE) 172 80-53-5 429 4-HYDRODfY-a,a,4-TRIlETNYL- (TERPINHYDRATE) 172 'D0-S3-S CYCLOHEXANENETHANOL 1629 48.5 , CYCLOHEXANE-1,2-DIOL, 1,3,3-TRIMETNYL- 1S8 38713-11-0 1716 47.3 CYCLOHEXANE-1,2-DIOL, 1-NETNYL- 130 6296-84-0 1630 53.7 CYCLOHEXANE-1,2-DIOL, 1-METHYL- (ismr of #1716) 130 • 1660 53.8 CYCLOHEXANE-1,2-DIOL, 4-METHYL- 130 23832-27-1 1814 55.3 CYCLOHEXANE-1,2-DIOL (trans) 116 931-17-9 1996 30.2 CYCLOHEXANE-1,3-DIENE 80 S92-57-4 140 126-81-8 1808 54.8 CYCLOHEXANE-1,3-DIONE, 5,5-DINETHYL- 2000 34.1 CYCLOHEXANE-1,4-DIENE 80 ' 628-41-1 1941 5.5 43.7 CYCLOHEXANE-1,4-DIENE, 1-METNYL- 94 4313-57-9 1710 55.5 CYCLOHEXANE-1,4-DIOL, 2,2,6-TRINETHYL- 1S8 S4993-31-6 1813 55.7 68.4 CYCLOHEXANE-1,4-DIOL (CUINTOL) 116 SS6-48-9 184 47.3 CYCLOHEXANE-1,4-D10NE 112 637-88-7 1566 47.3 CYCLOHEXANE-1,4-DIONE 112 63T-88-7 132 33.7 CYCLOHEXANOL, 5-METHYL-2-(1-METNYLETHYL)- (MENTHOL) 156 89-78-1 1959 51.0 CYCLOHEXANONE 98 108-94-1 1526 29.5 CYCLOHEXANONE, 2,3-EPOHY-3,S,S-TRINETHYL- 154 1944 17.0 56.0 CYCLOHEXANONE, 2-METHYL- 112 583-60-8 1673 29.7 CYCLOHEXANONE, 2-HETHYL-5-(1-NETHYLETHYL)- (CARVOMENTNONE) 1S4 59471-80-6 1512 51.8 CYCLOHEXANONE, 2-(1-CYCLOHE)CEN-1-YL)- 178 1502-22-3 1962 18.1 56.2 CYCLOHEXANONE, 3-HETHYL- 112 591-24-2 1717 52.8 CYCLOHEXANONE, 4-NYDROHY-2,2,6-TRIMETHYL- 156 20S48-02-1 1968 18.5 57.1 CYCLOHEXANONE, 4-METHYL- 112 589-92-4 1769 26.7 CYCLOHEXANONE, S-NETHYL-2-(1-IETHYLETNYL)- (NENTHONE, RT-iso25.0) 1S4 104S8-14-7 443 40.4 CYCLOHEXAN-1,4-D10NE, 2,6,6-TRIHETHYL- 154 20S47-99-3 1420 CYCLOHEXA-1,3-DIENE-1-CARBOXALDEHYDE, 2,6,6-TRIMETHYL- 1S0 116-26-7 1934 2.2 31.7 CYCLOHEXENE 82 110-83-8 1993 46.7 CYCLOHEXENE, 1,3-DIHETHYL- 110 2808476-6 1997 46.7 CYCLOHEXENE, 1,4-DINETHYL- 110 70688-47-0 2059 3.2 41.1 CYCLOHEXENE, 1-NETNYL- 96 591-49-1 2005 12.6 68.5 CYCLOHEXENE, 1-NETNYL-4-(1-NETNYETHENYL)- 136 138-86-3 161 12.7 63.1 CYCLOHEXENE, 1-NETHYL-4-(1-NETNYLETHENYL)- (LIMONENE-t) 136 5989-54-8 2006 12.7 64.1 CYCLOHEXENE, 1-METHYL-4-(1-NETHYLETHENYL)- (LINONENE-S-(-)) 136 5989-94-8 2055 2.6 38.1 CYCLOHEXENE-1, 3-METHYL- 96 591-48-0 2049 2.6 38.2 CYCLOHEXENE-1, 4-NETHYL- 96 591-67-9 . 48 37.3 CYCLOHEXENE-I-HETHANOL, atpha,atpha,4-TRINETHYL-3- (TERPINEOL, alpha-) 1S4 10482-56-1 195 37.3 CYCLOHEXENE-I-HETHANOL, atpha,alpha,4-TRINETNYL-S- (TERPINEOL, etpha-) 154 10482-56-1 1524 61.5 CYCLOHEXENONE-2, 4-HYDROHY-3,S,S-TRiNETNYL- 154 14203-59-9 1562 38.1 CYCLOHEXEN-I-ONE, 2-METHYL-S-(1-NETNYLETHYL)- (CARVONE-d) 150 99-49-0 1422 CYCLOHEX-I-EN-1-CARBOXALDEHYDE, 2,6,6-TRINETHYL- 1S2 432-25-7 806 23.5 53.9 CYCLOHEX-2-EN-I-ONE 96 930-68-7 444 23.5 53.8 CYCLOHEX-2-EN-1-ONE 96 930-68-7 1639 21.7 CYCLOHEX-2-EN-1-ONE, 2,6,6-TRIMETNYL- 138 20013-73-4 1863 31.9 CYCLOHEX-2-EN-I-ONE, 2-NETHYL-S-(1-IN:THYLETHYL)- (CARVONE, DIHYDRO-) 1S2 43205-82-9 1887 31.2 CYCLOHEX-2-EN-1-ONE, 3,5,5-TRINETHYL- 138 78-59-1 1557 38.0 CYCLOHEX-2-EN-I-ONE, 3-METHYL-6-/ETNYLETHYL-TETRAHYDRO- (PIPERITONE) 1S2 89-81-6 194 55.0 CYCLOHEX-2-EN-1-ONE, 3-METHYL-6-(1-METNYLETNYL)- (PIPERITONE) 152 675-20-7 1714 71.4 CYCLOHEX-2-EN-I-ONE, 4-HYDR01<YiIETNYL-3,S,5-TRINETHYL- 168 23069-00-3 1690 71.2 CYCLOHEX-2-EN-1-ONE, 4-HYDRONY-3 S,S-TRINETNYL-4-(3-/ETNYL-1,3-DIBUTENE)- 220 1679 69.6 CYCLOHEX-2-EN-1-ONE, 4-(1-BUTEN-i-ON-1-YL)-3,S,9-TRIIETNYL- 206 20194-68-7 1657 37.6 CYCLOHEX-2-EN-1-ONE 6-NETHYL-3-(1-NETHYLETNYL)- (CARVENONE) 1S2 499-74=1 8 1622 78.3 4-(3-HYDROHY-1-BUTYNYL)-3,S,S-TR1lETHYL- (CAS/58023-72-6) 208 31162-43-5 CYCLOHEX-3-EN-1-OL, 1355 CYCLOHEX-3-EN-I-ONE 96.6M-34-8 25

TOBACCO.WK1 Retention Time Databese - Septeetier 5, 1989 Sorted by Ca.pand Name RT (min) CMPD ----------- 0 DBWAX DB1 COMPOUND NAME ---• ----- ----- ----------------------------------------------------------------------- 1677 57.3 CYCLOHEX-S-EN-1-ONE, 2-ACETYL-3,3,5-TRiMETHYL- 2196 69.7 CYCLOPENTADIONE-1,3 2050 1.6 26.4 CYCLOPENTANE, METHYL- 1423 CYCLOPENTANECARBODULDEHYDE, 2-HYDRONY-1-NETHYL- 808 CYCLOPENTANE-1,2-DIONE, 3,3-DINETHYL- - 807 43.4 CYCLOPENTANE-1,2-DIONE, 3,4-DINETHYL- (SR82D) 810 41.6 CYCLOPENTANE-1,2-OIONE, 3,5-DINETHYL- 809 CYCLOPENTANE-1,2-DIONE, 3-ETHYL- 1625 43.0 61.6 CYCLOPENTANE-1,2-DIONE, 3-NETHYL- (CYCLOTENE) 90 CYCLOPENTANE-1,2-DIONE, 3-METHYL- (CYCLOTENE) 1715 86.5 CYCLOPENTANE-1,2-DIONE, 3-PHENYL- 1662 46.4 CYCLOPENTANE-1,2-D10NE, 3-(1-NETHYLETHYL)- (SR840) 282 73.5 CYCIOPENTANE-1,3-DIONE, 2-ETHYL-, (SWW72D) 811 CYCLOPENTANE-1,3-DIONE, 2-METNYL- (SR208D) 1681 50.3 CYCLOPENTANE-1,4-D1ONE, 2-HYDRONY-3,5,S-TRIMETHYL- 448 11.5 40.6 CYCLOPENTANONE 1640 24.7 CYCLOPENTANONE, 2,3-EPOXIDE-3-METHYL- 2031 13.2 51.2 CYCLOPENTANONE, 2,4-DINETHYL- 2019 13.2 51.2 CYCLOPENTANONE, 2,4-DIHETHYL- 2020 13.6 51.8 CYCLOPENTANONE, 2,4-DIMETHYL-, (isomer of 82019) 2032 13.6 CYCLOPENTANONE, 2,4-DINETHYL-, (isomer of 82031) 1509 12.1 CYCLOPENTANONE, 2,5-DINETHYL- 1978 12.9 46.2 CYCLOPENTANONE, 3-METHYL- 1104 CYCLOPENTAPYRAZINE-SH, 2,3-DINETHYL- 1103 CYCLOPENTAPYRA2INE-SH, 2-ETHYL- 1105 CYCLOPENTAPYRAZINE-5N, 6,7-DINYDRO- 591 CYCLOPENTAPYRAZINE-5H, 6,7-DINYDRO-2,3-DINETHYL- 590 CYCLOPENTAPYRAZINE-5H, 6,7-DIHYDR0-2-ETHYL- 588 37.7 CYCLOPENTAPYRAZINE-5H, 6,7-DINYDR0-2-METHYL- (SB6148D) 592 CYCLOPENTAPYRA2INE-5H, 6,7-DIHYDRO-5-ETHYL- 589 33.4 CYCLOPENTAPYRAZINE-SH, 6,7-DIHYDRO-S-METHYL- (SB6216D) 2112 1.6 18.7 CYCLOPENTENE 1992 1.9 29.0 CYCLOPENTENE, 1-METHYL- 1927 19.4 44.1 CYCLOPENTEN-2-ONE 461 CYCLOPENTEN-2-ONE, 2,3,5-TRINETHYL- 449 28.4 CYCLOPENTEN-2-ONE, 2,3-DINETHYL- 450 19.6 CYCLOPENTEN-2-ONE, 2,4-DIMETHYL- 1511 19.1 CYCLOPENTEN-2-ONE, 2,5-DINETNYL- 451 CYCLOPENTEN-2-ONE, 2,5-DINETHYL- 452 CYCLOPENTEN-2-ONE, 2-ETHYL- 456 CYCLOPENTEN-2-ONE, 2-ETHYL-3-METHYL- (SR18D) 352 CYCLOPENTEN-2-ONE, 2-ETHYL-S-NETHYL- (SWW199D) 336 CYCLOPENTEN-2-ONE, 2-HYDROXY-4-PROPYL- (SW11166D) 458 20.1 51.6 CYCLOPENTEN-2-ONE, 2-METHYL- (NAME WRONG IN TOBACCO.Lt) 1697 28.9 CYCIOPENTEN-2-ONE, 2-NETHYL-4-(1-METNYLETHYL)- 814 CYCLOPENTEN-2-ONE, 2-METNYL-4-(1-NETHYLETNYL)- (SNN129D) 813 CYCLOPENTEN-2-ONE, 2-(2-OXOPROPYL)- (SR38D) 453 CYCLOPENTEN-2-ONE, 3,4-DIMETHYL- 454 26.2 CYCLOPENTEN-2-ONE, 3,5-DIMETHYL- 398 CYCLOPENTEN-2-ONE, 3(4)-NETHYL-4(3)-ETNYL- (SW1R52D) 455 CYCLOPENTEN-2-ONE, 3-ETHYL- 457 CYCLOPENTEN-2-ONE, 3-ETHYL-2-METHYL- 427 CYCLOPENTEN-2-ONE, 3-ETHYL-4-NYDROD(Y- (SiN219D) 402 CYCLOPENTEN-2-ONE, 3-ISOPROPYL• (SW2SOD). 460 27.3 56.8 CYCLOPENTEN-2-ONE, 3-METHYL- 812 54.2 CYCLOPENTEN-2-ONE, 3-METHYL-2-(2-00(OPROPYL)- (SR42D) 459 CYCLOPENTEN-2-ONE, 3-PROPYL- (SWY24bD) 405 CYCLOPENTEN-2-ONE, 3-PROPYL- (SW11246D) 332 CYCLOPENTEN-2-ONE, 3-(2-FURYL)- (SWW1690) 1663 48.0 CYCLOPENTEN-2-ONE, 4-ACETOXY-3-METHYL- 1680 46.0 CYCLOPENTEN-2-ONE, 4-ACETYL-3 5,5-TRINETHYL- 1665 60.8 CYCLOPENTEN-2-ONE, 4-HYDROXY-J-NETNYL- 1879 33.3 CYCLOPENT-4-EN-1,3-D10NE 2182 38.5 CYCLOPENT-4-EN-1,3-DIONE, 2,4-DINETHYL- 1812 13.5 CYCLOPROPYL CARBINOL 1561 27.6 75.3 DECANAL 189 27.6 75.3 DECANAL 1954 5.6 61.6 DECANE 1428 42.4 83.3 DECANE-2,4-DIENAL, TRANS,TRANS 1883 60.1 83.0 DECANOIC ACID 2151 33.1 DECANOIC ACID, METHYL ESTER MY CAS Nl31BER 180 69874-67-S-- - 98 3859-41-4 84 96-37-7 128 20497-93-2 126 72692-92-3 126 13494-06-9 126 13494-07-0 126 13494-08-1 112 765-70-8 112 765-70-8 174 69745-71-7 140 60386-55-2 126 823-36-9 112 765-69-5 170 84 120-92-3 112 17024=44-1 112 1121-33-1 112 1121-33-1 112 112 112 4041-09-2 98 1757-42-2 146 61929-05-3 146 65129-00-2 120 23747-47-9 148 38917-63-4 148 38917-60-1 134 23747-46-8 148 52517-53-0 134 23747-48-0 68 142-29-0 82 693-89-0 82 930-30-3 124 54562-24-2 110 1121-05-7 110 23048-13-7 110 4041-11-6 110 4041-11-6 110 2931-10-4 124 S682-72-4 124 78210-64-7 140 82147-26-0 96 1120-73-6 138 61892-83-9 138 61892-83-9 138 61892-84-0 110 30434-64-1 110 931-22-6 124 30434-68-5 (30434-6 110 5682-69-9 124 41496-77-9 126 78210-63-6 124 1619-28-9 96 2758-1&1 152 3727-35-3 124 3S9S3-18-S 124 3S9S3-18-S 148 78210-65-8 154 180 112. 10288-24-1 96 930-60-9 124 72 2516-33-8 156 112-31-2 1S8 112-31-2 ~ 142 ' 124-18-5, m 1S2 25152-84-S ~ 172 334-48-5 m 186 110-42-9 Oo G) Do 26

TOBACCO.WK1 Retention Tiwe Database - Septeaiber 5, 1989 RT (min) CMPD ----------- Sorted by Cqmpound Nase S DBWAX DB1 CONPOUND NANE MW CAS NtllBER ---- 323 ----- ----- ----------------------------------------------------------------------- FORNANIDE, N-PENTYL- (SW180D) 11S .2591-7!9-9 -- 340 FORMANIDE, N-(2-FURANYLNETHYU- (SW192D) 12S 72693-10-8 324 FORMAMIDE, N-(3-METNYLBUTYL)- (SW181D) 11S 10285-87-7 417 FORNAMIDE, N-(3-PYRIDINYLMETHYU- (SY1234D) 136 56625-04-8 419 FORNAMIDE, N-(5-METHYLPYRROLYL-2-ETHYL)- (SIAQ30D) 152 1545 40.5 FORMIC ACID, 2-PHENYLETHYL ESTER (BENZENEETHANOL FORMATE) 150 104-62-1 1572 36.0 FORMIC ACID, PHENYLNETHYL ESTER 136 104-57-4 1216 2.1 12.3 FURAN 68 110-00-9 1352 FtJRAII, 2,3-DIHYDRO-2-NETHYL- 84 1708-25-4 1219 FIAtAN, 2,4-DINETHYL- 96 3710-43-8 1902 6.5 FURAN, 2,5-DIETHYL-TETRAHYDRO- 128 41234-48-9 1351 FURAN, 2,5-DIHYDRO- 70 1708-29-8 2135 21.2 52.2 FURAN, 2,5-DIHYDRO-2,5-DINETNOXY- 130 332-77-4 1977 4.3 33.4 FURAN, 2,5-DINETHYL- 96 625-86-5 1218 4.3 33.4 FURAN, 2,5-DIMETNYL- 96 625-86-5 1522 32.7 FURAN, 2-ACETIC ACID, ETHYL ESTER 154 4915-21-3 89 27.8 52.0 FURAN, 2-ACETYL- (ETHANONE,1-(2-FURAIIYL)-) 110 1192-62-7 1217 FURAN, 2-BUTYL- 124 4466-24-4 1220 FURAN, 2-ETHENYL- 94 1487-18-9 2023 4.0 32.9 FURAN, 2-ETHYL- 96 3208-16-0 629 FURAN, 2-ETHYL- 96 3208-16-0 630 FURAN, 2-ETHYL-S-METHYL- 110 1703-52-2 1353 2.8 FURAN, 2-NETHYL- 82 534-22-5 631 2.8 FURAN, 2-METHYL- 82 S34-22-5 1221 FURAN, 2-NETHYL-5-ETHENYL- 108 10504-13-9 880 FURAN, 2-METHYL-TETRAHYDRO- 86 96-47-9 1224 FURAN, 2-PHENYL- 144 17113-33-6 1703 53.1 FURAN, 2-(1-OXO-2-HYDROD(YETHYL)-S-HETHYL- 140 1222 77.3 FURAN, 2-(2-FURAIIYLNETHYL)-5-NETHYL- 162 13678-51-8 632 FURAN, 2-(2-METHYL-1-PROPENYL)- 124 10504-11-7 1223 FURAN, 3-NETHYL- 82 930-27-8 1969 3.4 32.1 Fl1RAN, 3-NETHYL-TETRAHYDRO- 86 108-03-2 1225 . Fl1RAN, 3-PHENYL- 144 13679-41-9 875 . FURAN, TETRAHYDRO- 72 109-99-9 653 flIRANACETIC ACID-2 126 2745-26-8 2036 21.3 41.1 FURANCARBONITRILE-2 93 617-90-3 64 30.3 FURANCARBOXALDEHYDE-2, 5-METHYL- (SR54C) 110 620-02-0 163 30.7 56.3 FURANCARBOXALDEHYDE-2, 5-METHYL-; (SR54D) 110 620-02-0 1560 25.0 FURANCARBOXALDEHYDE-2, (FURFURAL) 96 98-01-1 162 25.2 44.4 FURANCARBOXALDEHYDE-2, (FURFURAL) 96 98-01-1 1354 FURANCARBOXALDEHYDE-3 96 498-60-2 201 63.0 FURANCARBOXAMIDE-2 111 609-38-1 1575 63.0 FINtAIiCARBOXANIDE-2 111 609-38-1 344 FURAIICARBOXAMIDE-2, N-(2-FURANYLNETHYL)- (SW192D) 125 61190-74-7 655 67.0 FURANCARB00(YLIC ACID-2, 5-METHYL- 126 1917-15-3 1770 31.2 FURANCARBOXYLIC ACID-2, METHYL ESTER 126 611-13-2 675 FURANCARBOXYLIC ACID-2, TETRANYDRO-5-OXO-, METHYL ESTER 144 3885-29-8 1668 58.8 FURANCARBOXYLIC ACID-2, TETRANYDRO-S-OXO-, METHYL ESTER 144 3885-29-8 695 FURANCARBOXYLIC ACID-2, TETRAHYDR0-S-00(0-, METHYL ESTER 144 3885-29-8 694 FURANCARBONYLIC ACID-2, TETRARYDRO-S-OXO-, METHYL ESTER 144 3885-29-8 654 66.0 63.2 FURANCARBOXYLIC ACID-2, (FUROIC ACID-2) 112 88-14-2 179 58.4 58.4 FURANCARBOI(YLIC ACID-3 117 488-93-7 1891 59.8 FURANCARBOXYLIC ACID-3, 5-METHYL- 126 21984-93-0 1711 58.6 FURANCARBOHYLIC ACID-3, TETRAHYDRO-5-OXO-, NETHYL ESTER 144 4694-67-1 795 49.0 FURANDICARBOXIILDEHYDE-2,5 124 823-82-5 1388 FURANDIONE-2,5, 3,4-DIETHYL-, (NALEIC ANHYDRIDE, 3,4-DIETHYL-) 1S6 28843-39-2 951 38.4 FURANDIONE-2,5, 3,4-DINETHYL-, (NALEIC ANHYDRIDE, 3,4-DINETHYL-) 126 766-39-2 1387 FURANDIONE-2,5, 3-METHYL-4-PHENYLMETHYL- (3-MALEIC ANHYDRIDE, 4-BENZYL-3-NETH 202 72693-16-4 206 41.4 FURANDIONE-2,5, 3-HETHYL-4-PROPYL-, (NALEIC ANHYDRIDE, 3-METHYL-4-PROPYL-) 154 16493-20-2 164 34.9 46.5 FURANNETHANOL 98 98-00-0 1623 34.9 46.5 FURANNETHANOL 98 98-00-0 1789 29.9 58.9 FURANlETHANOL-2, ACETATE 140 623-17-6 1531 27.2 FURANIN:THANOL-2, FORNATE 126 13493-97-5 716 FtJRANONE-2(3H), 3-HYDROD(YMETHYL-5-METHYL- 128 61892-58-8 1750 35.5 FURANONE-2(3H), 5-ETHENYLDINYD.RO-S-lNETHYL- (SR66C) 126 1073-11-6 702 FIAtANONE-2(3H), 5-GLYCOL ACETATE (SNN780) 188 175 24.2 FURAHONE-2(3H), 5-METHYL- (a-ANGELICALACTONE) 98 591-12-8 1806 32.6 50.0 FtXtANONE-2(3H), DINYDRO- . 86- 96-48-0 107 32.6 50.0 FURANONE-2(3H), DIHYDRO- 86 96-48-0 683 32.6 50.0 FURANONE-2(3H), DINYDRO- 86 96-48-0 1647 66.2 FURANONE-2(3H), DIHYDRO-3,3-DIMETHYL-4-NYDROD(Y- 130 72902-81-9 28

TOBACCO.WK1 Retention Time Databese - Septeaber 5, 1989 RT (min) CNPD ----------- Sorted by Campound Nama # DBWAX DB1 CONPOUND NAME HY CAS NUNBER ---- ----- ----- ----------------------------------------------------------------------- 1898 57.6 FURANONE-2(3H), DIHYDRO-3,3-DINETNYL-S-(2-ONOPROPYL)- (SR106C) 170 38273-97-1 1578 37.1 FURANONE-2(3H), DIHYDRO-3,4,S-TRINETNYL- 128 85564•78-9 687 FURANONE-2(3H), DIHYDRO-3,4-OIHYDROXY-3-NETHYL- (SNN117D) 132 63700-30-1 712 FURANONE-2(3H), DIHYDRO-3,4-DIHYDROOfY-S-METHYL- 132 710 FURANONE-2(3H), DINYDRO-3,4-Oi0N-5-HYDRONYMETHYL- 148 674 FURANONE-2(3H), DIHYDRO-3-11CETOf(Y- (SR1090) 144 672 FURANONE-2(3H), DIHYDRO-3-IlCETOi(Y-4-NYDROXY- (SR1540) 160 676 48.6 66.6 FURANONE-2(3N), DIHYDRO-3-IICETYL- (SR2300) 128 517-23-7 1648 63.3 FURANONE-2(3H), DINYDR0-3-NYDRONYMETNYL- 116 18132-98-4 684 FURANONE-2(3H), DIHYDRO-3-NYDRO~YIETHYL- 116 18132-98-4 1525 56.6 FURANONE-2(3H), DIHYDRO-3-HYDRO~fY- 102 19444-84-9 686 58.2 FURANONE-2(3H), DIHYDR0-3-NYDRONY-, PR0P10NATE 158 25600-22-0 677 FURANONE-2(3H), DIHYDRO-3-NYDROXY- (SR43DY 102 19444-86-9 1659 50.2 FURANONE-2(3N), DINYDR0-3-NYDROXY-3,4,4-TRIHETHYL- 144 2127 51.6 62.3 FURANONE-2(3H), DINYDR0-3-NYOROD(Y-4,4-DINETHYL- 130 707 56.8 FURANONE-2(3H), DIHYDR0-3-NYDR00(Y-S-NETHYL- 116 S3S61-62-9 1646 54.8 FURANONE-2(3H), OINYDRO-3-NYDROxY-5-NETIIYL- (ISOMER OF 707) 116 700 FURANONE-2(3H), DINYDRO-3-IIYDROHY-S-(1-NYDROD(YETHYL)- 146 699 FURANONE-2(3H), DINYDRO-3-HYDROHY-S-(1-NYDRODfYETHYL)- (isomer) 146 698 FURANONE-2(3H), OIHYDRO-3-HYDROHY-S-(1-NYDR00(YETHYU- (ISOMER) 146 701 FURANONE-2(3H), DINYDRO-3-HYDRONY-S-(2-NYDROXYETNYL) 146 61892-52-2 697 FURANONE-2(3H), DIHYDR0-3-HYDRODfY-5-(2-HYDROxYETNYL)-S-NETHYL- 160 61892-50-0 1947 31.1 54.0 FURANONE-2(3H), DINYDRO-3-METHYL- 100 1679-47-6 1786 37.0 FURANONE-2(3H), DINYDR0-3-(1-NETNYLETHYL)- (SR42C) 128 1608-63-5 1759 37.9 FURANONE-2(3H), DINYDRO-3-(1-HETHYLETNYL)- (SR42C) 128 1608-63-5 1499 59.9 FURANONE-2(3H), DIHYDRO-3-(2-00(OPROPYL)- 142 71385-84-7 685 FURANONE-2(3H), DIHYDR0-3-(2-00(YPROPYU- 142 71385-84-7 679 FURANONE-2(3H), DIHYDRO-4,4-DINETNYL-3-HYDROXY- 130 S2126-90-6 2129 67.8 79.5 FURANONE-2(3H), DiNYDRO-4,4-DINETHYL-5-NYDROD(YMETHYL- 14i 1796 35.1 FURANONE-2(3H), DINYDRO-4,5,S-TRIMETHYL- 128 2981-96-6 1760 35.1 FURANONE-2(3H), DINYDRO-4,5,5-TRINETNYL- 128 2981-96-6 68 31.9 FURANONE-2(3H), DIHYDRO-4,5-OINETNYL- (SR67C) 114 6971-63-7 70 32.4 FURANONE-2(3H), DIHYDRO-4,5-DIHETNYL- (SR73C) 114 6971-63-7 673 FURANONE-2(3H), DINYDR0-4-ACETOD(Y-5-HYDRO)(Y- 160 1523 62.6 FURANONE-2(3H), D I HYDRO-4-11CETYl- 128 7400-67-1 71 FURANONE-2(3H), DIHYDRO-4-ET8YL- (SR74C) 114 16i96-51-8 1785 37.8 FURANONE-2(3H), DIHYDRO-4-ETNYL- (SR74C) 114 1"96-51-8 678 FURANONE-2(3H), DINYDR0-4-NYDR00(Y- (SR52D) 102 5469-16-9 1538 71.5 FURANONE-2(3H), DINYDRO-4-HYDROXY- (SR54D) 102 5469-16-9 680 FURANONE-2(3H), DINYDRO-4-NYORONY-3-NYDROD(YIN:THYL- 132 61892-45-3 681 FURANONE-2(3H), DIHYDR0-4-HYDRONY-4-IETNYL- 116 34945-05-6 1643 33.0 FURANONE-2(3H), DIHYDRO-4-METHYL- 100 1679-49-8 1661 32.9 FURANONE-2(3H), DIHYDRO-4-METHYL- (SR76C) 100 1679-49-8 1787 40.3 FtlRANONE-2(3H), DINYDRO-4-(1-11ETHYLETHYL) (SR71C) 128 10547-88-3 69 FURANONE-2(3H), DiNYDR0-4-(1-IETHYLETHYL) (SR71C) 128 10547-88-3 1761 31.6 FURANONE-2(3H), DIHYDRO-S,5-DINETHYL- 114 3123-97-5 696 FURANONE-2(3H), DIHYDRO-5-ACETYL- (SR75D) 128 29393-32-6 1782 46.4 78.6 FURANONE-2(3H), DIHYDRO-5-BUTYL- 142 104-S0-7 1772 37.0 63.3 FURANONE-2(311), DIHYDRO-5-ETHYL- 114 695-06-7 1797 59.7 98.0 FURANONE-2(3H), DINYDR0-5-HEPTYL- 184 96 55.4 FURANONE-2(3H), DINYDRO-5-NEXYL- (p-DECALACTONE) 170 706-14-9 708 FURANONE-2(3H), DIHYDRO-S-NYDROOfYMETHYI- 116 10374-S1-3 150 32.1 54.2 FURANONE-2(3H), DINYDRO-S-METNYL- (0-PENTYLLACTONE) 100 108-29-2 1896 53.8 FURANONE-2(3H), DIHYDR0-5-NETHYL-S-(3-NE-1-BUTENYL)- 168 20 50.9 85.5 FURANONE-2(3H), DINYDRO-5-PENTYL- 156 104-61-0 108 41.5 FURANONE-2(3H), DINYDRO-S-PkOPYI- (0-HEPTALACTONE) 114 10S-21-5 242 FURANONE-2(3H), DIHYDRO-S-(1-NYDROXYETHYL)- 130 54621-96-4 682 FURANONE-2(3H), DIHYDR0-5-(1-NYDRONYETNYL)- 130 27610-27-1 1588 64.3 FURANONE-2(3N), DINYDRO-S-(1-HYDRONYETHYL)- 130 S4621-96-4 1207 FURANONE-2(3H), DINYDRO-5-(1-ONOPROPYL)- 142 61892-49-7 246 85.5 FURANONE-2(3H), DIHYDR0-5-(3-PYRIDYL)- 163 20971-79-3 668 38.4 49.9 FURANONE-2(5H) 84 2082S-71-2 363 FURANONE-2(5H), 3,4,5-TRIMETNYL- 126 33488-51-6 713 FURANONE-2(5H), 3,4,5-TRINETHYL- 126 33488-51-6 1644 42.8 FURANONE-2(5H), 3,4,5-TRIMETHYL- 128.33488-51-6 359 FURANONE-2(5H), 3,4-DIMETHYL- 112 1575-46-8 1527 43.3 FURANONE-2(5H), 3,4-DIHETHYL- 112 1575-46-8 66 FURANONE-2(5H), 3,4-DINETNYL-S-PENTYL- (DINYDROBONOLIDE, SR57C) 182 10547-84-9 1757 31.5 FURANONE-2(5H), 3,5,5-TRINETHYL- 128 50598-50-0 714 FURANONE-2(5H), 3,5-DINETHYL- 112 3S84-69-0 365 FURANONE-2(5H), 3,5-DIMETHYL- (SNN88D) 112 5S84-69-0 29

TOBACCO.WK1 Retention Time Database - Septmaber S, 1989 Sorted by Cowpotsd Nam RT (min) CMPO ----------- * DBWAX DB1 COMPOUND NAME MW CAS NUMBER -------------------------------------------------------------------- --- 667 FURANONE-2(5H), 3-ACETYL-4-IETHYL- 140 61892-42-0 670 37.4 FURANONE-2(SH), 3-METHYL- 98 22122-36-7 360 FURANONE-2(SH), 3-METHYL- 98 22122-36-7 706 FURANONE-2(SH), 3-METHYL-S-METHYLENE- 110 61892-54-4 669 FURANONE-2(5H), 3-(1-METNYLETHYL)- 126 7754-93-0 366 43.3 FURANONE-2(SH), 4,5-DIMETHYL- (SR100C) 112 10547-85-0 1624 45.4 FURANONE-2(SH), 4-METHYL- 98 6124-79-4 1645 45.3 FURANONE-2(5H), 4-METHYL- 98 6124-79-4 671 FURANONE-2(5H), 4-METHYL- 98 6124-79-4 704 FURANONE-2(5H), S-ACETYL- (SNN128D) 126 73 39.3 FURANONE-2(SH), 5-ETHYL- (SR79C) 112 2407-43-4 362 FURANONE-2(5H), 5-ETHYL-3-METHYL- (SR80D) 126 26329-68-0 703 FURANONE-2(SH), 5-ETHYL-3-METHYL- (SR80D) 126 26329-68-0 156 31.3 FURANONE-2(SH), 5-METHYLENE- (PROTOANEMONIN) 96 '108-28-1 715 24.2 FURANONE-2(5H), S-METHYL- (b-ANGELICA LACTONE) 98 S91-11-7 364 35.8 FURANONE-2(5H), 5-METHYL- (b-ANGELICA LACTONE) 98 591-11-7 1888 51.6 FURANONE-3(2H), 4-HYDR01(Y-2,S-DIMETHYL- (FiNiANEOI) 128 3658-77-3 1600 25.0 FURANONE-3(2H), DIHYDRO-S-METNYL-S-PROPYL- 142 3284-93-3 950 FURAN-2,5-DIONE (MALEIC ANHYDRIDE) 98 108-31-6 952 FURAN-2,5-DIONE, 3-ETHYL-4-METHYL- 140 3552-33-8 1389 FURAN-2,5-DIONE, 3-PROPYL- (SUCCINIC ANHYDRIDE, 3-PROPYL-) 140 83174-26-9 954 FURAN-2,5-DIONE, DIHYDRO- (SUCCINIC ANHYDRIDE) 100 108-30-5 955 FURAN-2,5-DIONE, DIHYDRO-3,4-DINETHYL- 128 7425-92-5 956 FURAN-2,5-DIONE, DIHYDRO-3-METHYL- (SUCCINIC ANHYDRIDE, 3-METHYL-) 114 4100-80-5 1430 FURFURALDEHYDE, 3-METHYL- 110 33342-48-2 1429 FURFURALDEHYDE, 5-ACETYL- 138 32529-53-6* 794 68.3 FURFURALDEHYDE, 5-HYDROXYMETHYL- 126 67-47-0 1910 77.1 FURFURALDEHYDE-2, 5-(2-PHENYLETHENYL)- 198 1431 23.4 42.3 FURFLJRALDEHYDE-3 96 498-60-2 1687 27.8 FURFURYL ALCOHOL, TERAHYDRO- 102 97-99-4 339 FUROAMiDE,N-ETHYL- (S11H191) 139 836 GLUCOPYRANOSE-B-D, 1,6-ANHYDRO- (LEVOGLUCOSAM) 162 498-07-7 284 HARMANE, (1-ME-9H-PYRIDO[3,4-BI-1ND0LE)- (SWN63D) 182 486-84-0 2202 55.3 HENEICOSANE (C21 n-ALKANE) 296 629-94-7 1948 39.1 HEPTADECANE 240 629-78-7 1433 12.0 51.5 HEPTANAL 114 111-71-7 1775 12.0 51.5 HEPTANAL 114 111-71-7 1274 HEPTANAMINE 115 71412-05-0 2166 1.7 34.3 HEPTANE 100 142-82-S 1635 35.7 HEPTANE-1,2-DIONE 128 2363-85-1 1530 31.2 HEPTANE-2,5-DIONE 128 1506 31.1 HEPTANE-2,5-DIONE 128 1904 31.3 HEPTANE-2,5-DIONE, 6-METHYL- 142 13901-85-4 205 35.4 HEPTANE-2,6-DIONE 128 13505-34-5 127 48.4 HEPTANOIC ACID 130 111-14-8 1548 25.8 57.2 HEPTANOL-1 116 111-70-6 2084 21.6 57.1 HEPTANOL-2, 6-METHYL- 130 4730-22-7 2083 18.6 51.6 HEPTANOL-2(+/-) 116 S43-49-7 1550 11.9 50.2 HEPTANONE-2 114 110-43-0 1965 55.2 HEPTANONE-3, 5-METHYL- 128 541-85-5 1784 9.2 48.9 HEPTANONE-4 114 123-19-3 1966 57 8 H N NE -4 2 6- Y - 142 108-83-8 1779 30.8 EPTA ONE . , , DI TH L HEPTANONE-4, 5-HYDROXY- 132 39 31.5 HEPTAN-3,5-DIENE-2-ONE, 6-METHYL- 124 1604-2s-0 1432 HEPTA-2,4-DIENAL 110 S910-85-0 1838 27.1 HEPTA-2,5-DIEN-4-ONE, 2,6-DINETNYL- (PNORONE) 138 S04-20-1 1603 33.6 HEPTA-4,6-DIENOIC ACID, 6-METHYL-3-(1-METBYLETHYL)-, METHYL ESTER 196 80114-59-6 1974 1.8 33.1 HEPTENE-1 98 S92-76-7 1436 HEPT-2-ENAL, 2-tB:THYL- 126 56161-68-3 n HEPT-3-EN-2,5-DIONE, 6-METHYL- (SR41C) 140 21504-51-8 1746 35.9 HEPT-3-EN-2,5-DIONE, 6-METHYL- (SR41C) 140 21S04-51-8 1528 23.7 HEPT-3-EN-2-ONE; 5-(1-METHYLETNYL)- (SR131C) 1S4 S0767-76-5 1836 19.3 . HEPT-5-EN-2-ONE, 6-METHYL- 126 110-93-0 or 52522 1654 53.1 HEPT-6-EN-2-ONE, 5-(1-METHYLETHYL)-7-(TETRAHYDRO-2-METHYL-2-FURANYL) - 238 ST782-60-2 2130 73.0 HEXACOSANE 366 630-01-3 1889 33.1 100.3 HEXADECANE 226 544-76-3 1742 59.6 HEXADECANOIC ACID, METHYL ESTER (PALMITIC ACID, METHYL ESTER) 270 112-39-0 31 HEXADECANOIC ACID (PALMiTiC ACID) 256 57-10-3 1845 86.8 HEXADECANOIC ACID (PALMITIC ACID) 256 57-10-3 Ln 2178 65.1 113.9 HEXADECANOL-1 242 36653-82-4 f+ 9 46.9 HEXADECENE-1, 3-METHYLENE-7,11,15-TRIMETHYL-3-METHYLENE- (NEOPHYTAD IENE) 278 504-96-1 m 30

TOBACCO.WK1 Retention Time Database - Septewiber 5, 1989 RT (min) CMPD ----------- Sorted by Ccmpound Naoe S DBWAX DB1 COMPOUND NAME MII CAS NtAIBER ---- 8 ----- 46.9 ----- --------------------------------------- - - --- - - HEXADECENE-1, 3-METHYLENE-7,11,15-TRIMETHYL-3-METHYLENE- (NEOPHYTADIENE) 278 S04-96-1 1601 46.9 HEXADECENE-1, 3-METHYLENE-7 11,15-TRIMETHYL-3-METHYLENE- (NEOPHYTADIENE) 278 S04-96-1 55 70.1 HEXADEC-2-EN-1-OL, 3,7,11,1i-TETRAMETHYL- (PHYTOL) 296 1S0-86-7 2191 2.2 29.1 HEXADIENE-2,4 (CIS OR TRANS) 82 S92-46-1 2192 2.3 30.3 HEXADIENE-2,4 (TRANS OR CIS) 82 592-46-1 24 46.6 HEXAMETNYLENETETRAMINE 140 100-97-0 757 54.0 69.8 HEXAMIDE 115 628-02-4 1767 8.9 42.0 HEXANAL 100 66-25-1 1438 8.9 42.0 HEXANAL 100 66-25-1 1439 HEXANAL, 2-(1-METHYLETNYL)-5-OX0- 156 15303-46-5 1957 1.5 23.7 HEXANE 86 110-54-3 2171 17.4 48.7 NEXANENITRILE 97 628-73-9 2054 25.5 NEXANE-1,3-DIENE 82 S92-48-3 2038 22.7 HEXANE-1,4-D1ENE 82 592-45-0 2040 20.8 HEXANE-I,S-D1ENE 82 S92-42-7 1570 49.0 HEXANE-1,5-DIOL, 5-METHYL- 132 1900 9.2 40.2 HEXANE-2,3-DIONE 114 3848-24-6 2013 51.6 HEXANE-2,4-DIENAL 96 142-83-6 1437 51.6 HEXANE-2,4-DIENAL 96 142-83-6 2057 28.6 HEXANE-2,4-OIENE 82 592-46-1 2058 29.9 HEXANE-2,4-DIENE, ISOMER OF 82 848 43.8 58.9 NEXANE-2,5-DIOL 118 2935-44-6 818 28.0 52.1 HEXANE-2,5-DIONE 114 110-13-4 819 44.3 HE,fANE-2,5-DIONE, 3-HYDROXY- (SNN96D) 130 61892-85-1 126 HEXANOIC ACID 116 142-62-1 1821 48.1 HEXANOIC ACID, 2-ETHYL- 144 301-10-0 1606 17.1 HEXANOIC ACID, 2-ETHYL-, ETHYL ESTER 172 2983-37-1 204 NEXANOIC ACID, 2-METHYL- 130 4536-23-6 1832 70.6 HEXANOIC ACID, 2-(1-METHYLETHYL)-5-0X0- 172 16825-90-4 1542 34.5 HEXANOIC ACID, 3-HEXENYL ESTER 198 31501-11-8 1529 67.4 HEXANOIC ACID, 4-METHYL-S-OJ(0- 144 6818-07-1 656 HEXANOIC ACID, 4-OXO- 130 1117-74-4 1906 47.5 HEXANOIC ACID, 5-METHYL- 130 628-46-6 1905 16.1 NEXAlIOIC ACID, 5-METHYL-, METHYL ESTER 144 2177-83-S 258 HEXANOIC ACID, 5-OXO- (SiN40D) 130 3128-06-1 1549 14.2 HEXANOIC ACID, ETHYL ESTER 144 123-66-0 1551 52.5 HEXANOIC ACID, PHENYLNETHYL- 206 6938-45-0 1866 20.4 48.4 HEXANOL-1 102 111-27-3 2080 13.9 42.4 HEXANOL-2 102 626-93-7 849 HEXANOL-2, 2-METHYL- 116 625-23-0 2081 17.1 48.6 HEXANOL-2, 5-METHYL- 116 627-59-8 1685 13.1 HEXANOL-3 102 623-37-0 463 8.6 40.9 NEXANONE-2 100 591-.78-6 1964 47.3 HEXANONE-2, 5-METHYL- 114 110-12-3 469 HEXANONE-3 100 S89-38-8 1935 49.5 HEXA-2,4-DIENE, 2,5-DIMETNYL- 110 764-13-6 2169 6.0 HEXA-2,4-DIENE, 2,5-DIMETHYL- 110 764-13-6 2173 1.6 22.5 HEXENE-1 84 592-41-6 2042 1.6 24.8 HEXENE-2, (cis or trans) 84 4050-45-7 2041 1.6 23.7 HEXENE-2, (trans or cis) 84 4050-45-7 2052 23.4 HEXENE-3, trans- 84 13269-52-8 1440 HEXEN-2-AL, cis 98 50S-S7-7 1441 13.7 HEXEN-2-AL, trans 98 6728-26-3 1280 11.8 HEXYL AMINE 101 111-26-2 1709 51.2 HEX-2-ENOIC ACID, 5-METHYL-, (trans) 140 S1424-01-2 154 22.1 HEX-3-EN-1-OL, (eis)(trens R.T.22.6)(LEAF ALCOHOL) 100 928-96-1 1788 22.1 HEX-3-EN-1-OL, (cis)(trans R.T.22.6)(LEAF ALCONOL) 100 928-96-1 464 HEX-3-EN-2-ONE 98 763-93-9 1504 14.3 HEX-3-EN-2-ONE, 5-METHYL- 112 1821-29-0 1876 35.8 HEX-4-EN-1-OL, 5-METHYL-2-(1-METHYLETHYL) (LAMANDULOU 1S4 58461-27-1 1909 12.5 HEX-4-EN-3-ONE 98 25659-22-7 1907 23.8 HEX-5-EN-1-OL 100 $21-41-0 1356 23.8 HEX-S-EN-1-0L 100 821-41-0 1281 HYDRA2INE, 1,1-DIMETHYL- 60 57-14-7 929 IMIDAXOLIDINE-2,4-DIONE, 1-ETHYL- (HYDANTOIN, 1-ETHYL-) (SR241D) 128 61893-09-2 931 IMIDAXOLIDINE-2,4-DIONE, (1-METHYLETHYL)- (HYDANTOIN, 3-.(1-METHYLETHYL)- 142 63637-90-1 2128 63.5 1MIDA20LECARBOXALDEHYDE-2 96 10111-08-7 910 58.9 IMIDA20LE-1H 68 288-32-4 106 39.6 IMIDAZOLE-1H, 1,2-DIMETHYL- 96 1739-84-0 1615 37.5 IMIDAZOLE-IH, 1,4-DIMETHYL- 96 6338-45-0 1616 43.8 IMIDAZOLE-IH, 1,5-OIMETNYL- 96 10447-93-S 31

TOBACCO.WK1 Retention Time Database - Septeaber 5, 1989 Sorted by Cawpotrd Nawe RT (min) CNPD ----------- # DBWAX DB1 COMPOUND NAME MN CAS NUiBER ---- ----- ----- --------*--------------------------.....------------------------------- . - - 1330 IMIDAZOLE-1H, 1-ACETYL- 110 2466-76-4 1159 IMIDAZOLE-1H, 1-ETNYL- 96 7096-07-9 1614 35.8 51.8 1MIDAZOLE-1H, 1-METNYL- 82 616-47-7 101 35.8 51.8 IMIDA20LE-111, 1-METNYL- 82 616-47-7 1000 IMIDAZOLE-1N, 1-METNYL-2-(1-NETHYLETRYL)-5-(3-PYRIDYL)- (SEE #967) 201 78210-84-1 916 IMIDA20LE-1N, 2,4,5-TRIMETNYL- (SR228D) 110 822-90-2 86 58.4 INIDAZOLE-111, 2,4-DIMETNYL- 96 930-62-1 911 INIDAZOLE-111, 2,5-DINETNYL-4-(1-METHYLETHYL)- (SR215D) 138 40688-28-6 216 60.4 INIDAZOLE-1H, 2-ACETYL-4-MET8YL- 124 2524-90-5 1163 INIDAZOLE-111, 2-BUTYL- 124 '50790-93-7 912 56.5 63.3 INIDAZOLE-111, 2-ETNYL- 96 1072-62-4 915 68.3 IMIDAZOLE-111, 2-ETNYL-4-iETNYL- 110 931-36-2 914 IMIDAZOLE-111, 2-ETHYL-4-(1-NETHYLETNYI)- (SR221D) 138 1161 57.2 IMIDA20LE-1N, 2-METHYL- 82 693-98-1 917 55.1 IMIDA20LE-1N, 2-(1-METNYLETNYL)- (SR2110) 110 36947-68-9 209 57.5 IMIDAZOLE-1H, 2-(1-METNYLPROPYL)- 124 61093-06-9 213 61.3 INIDAZOLE-111, 4,5-DIlETNYL- 96 2302-39-8 304 INIDAZOLE-111, 4-ACETYL-2-IETNYL- (StiA1157D) 124 78210-66-9 1514 80.4 IMIDAZOLE-1H, 4-ACETYL-5-IETNYL- 124 23328-91-8 328 IMIDAZOLE-1H, 4-ACETYL•5-PROPYL- (SW172D) 152 78210-67-0 913 INIDAZOLE-111, 4-ETHYL- (SR2130) 96 19141-85-6 920 INIDAZOLE-111, 4-ETHYL-2-(1-METHYLETHYL)- (SR232D) 138 37455-59-7 217 59.6 IMIDAZOLE-1H, 4-METHYL- 82 822-36-6 919 55.5 IMIDAZOLE-1N, 4-METNYL-2-(1-METNYLETHYL)- (SR212D) 124 37455-58-6 1162 iMIDAZOLE-1H, 4-METNYL-2-(2-METHYLPROPYL)- (SR218D) 138 61893-07-0 918 1MIDAZOLE-1H, 4-(1-METBYLETNYL)- (SR2170) 110 S86S0-48-9 1282 INIDAZOLE-IH, 4-(2-ETHANEAMINE)- (NISTAMINE) 111 51-45-6 465 1MIDAZOLE-1N, 5-ACETYL-1-METNYL- 124 20970-50-7 922 1MIDAZOLE-1H, C5-ALKYL- (SR214D) 138 921 INIDAZOLE-111, CS-ALKYL- (SR2150) 138 923 IMIDAZOLE-1H, C5-ALKYL- (SR222D) 138 1239 IMIDA20LIDINETHIONE 102 96-+K-7 927 IMIDAZOLIDINE-2,4-DIONE, 1,S-DIMETNYL (HYDANTOIN,1,5-DINETHYL-) (SR1590) 128 17374-27-5 933 77.9 IMIDAZOLIDINE-2,4-DIONE, i-METHYL• (NYDANTOIN,1-METIIYL-) 114 616-04-6 934 IMIDA20LIDINE-2,4-DIONE, 3-METHYL- (NYDANTOIN, 3-METNYL-) 114 928 iMIDAZOLIDINE-2,4-DIONE, 5-ETNYL- (NYDANTOIN, S-ETBYL-) (SR157D) 128 15414-82-1 932 IMIDA20LIDINE-2,4-D10NE, 5-METBYL- (NYDANTOIN, 5-METNYL-) 114 616-03-5 930 IMIDAZOLIDINE-2,4-D10NE, 5-(1-METBYLETNYL)- (HYDANTOIN, S-(1-METHYLETNYL-)) 142 1693544-5 926 INIDAZOLIDINE-2,4-DIONE (NYDANTOIN) (SR1860) 100 461-72-3 780 IMIDAZOLIN-2-ONE-3, S-METBYL- (SR171D) 98 61892-75-9 1030 IMIDAZO-1H[2,1-a]ISOGUINOLINE 168 2126 58.9 80.1 IMIDA20[1,2-a]PYRIDINE 118 274•~6-0 968 58.8 IMIDAZO[1,2-a]PYRIDINE 118 274- 6-0 924 IMIDAZO[1,2-a]PYRIDINE, 2,3-DINETHYL- OR 2190) 146 875-80-9 620 IMIDAZO[4,5-b]PYRiDINE-1N, 2-METNYL- 133 68175-07-5 621 1MIDAZO[4,5-b]PYRIDINE-1N, 7-METNYL- (SB8194D) 133 275a2-20-3 1830 20.5 64.8 INDANE 118 496-11-7 466 50.3 81.5 INDANONE-1 132 83-33-0 1820 49.4 INDANONE-1, 3-METNYL- 146 6072-57-7 118 56.4 INDANONE-1, 4,7-DIMETNYL- 160 i037-60-5 1726 46.5 INDANONE-2 132 615-13-4 1913 70.2 INDAZOLE 118 271-44-3 2119 25.7 65.1 INDENE 116 95-13-6 1442 INDENE-5-CARBOXALDEHYDE, 2,3•DINYDRO- 146 30084-91-4 53 65.8 INDOLE 117 120-72-9 82 55.2 INDOLE, 1,2-DiMETNYL- 14S a75-79-6 83 INDOLE, 1,3-DIMETNYL- 145 a75-30-9 1052 INDOLE, 1,4-DIMETHYL- 145 27816-52-0 1053 INDOLE, 1,7-DINETHYL- 145 5621-16-9 79 48.1 INDOLE, 1-METHYL- 131 603-76-9 1078 INDOLE, 1-PNENYL- 193 1068 1NDOLE, 1.2,3-TRIMETNYL- 159 "1971-46-6 80 69.8 INDOLE, 2,3-DIMETHYL- 14S 91-55-4 1051 70.1 INDOLE, 2,5-DINETHYL- 145 1196-79-8 1060 INDOLE, 2,6-DINETHYL- 145 81 67.7 INDOLE, 2-METHYL- 131 95-20-5 1076 INDOLE, 2-PHENYL- 193 948-65-2 1054 INDOLE, 3,5-DINETHYL• 1056 INDOLE, 3,7,DIMETNYI- 145 145 3189-12-6 S621-14-7 1070 INDOLE, 3-ACETYL- 159 703-80-0 1055 INDOLE, 3-ETHYL- 145 1484-19-1 32

TOBACCO.YK1 Retention Time Database - Septaiber 5, 1989 Sorted by Campoutd Name RT (min) CNPD -------.... 0 DB11AX DB1 COMPOUND NAME Nw CAS NUMBER ---- ----- ----- ----------------------------------------------------------------------- ---- ------------- 85 67.5 INDOLE, 3-METHYL- (SKATOLE) 131 83-34-1 1077 INDOLE, 3-PHENYL- 193 1504-16-1 1069 INDOLE, 4,5,6-TRINETHYL- 159 1064 INDOLE, 4-METHYL- 131 16096-32-5 1061 INDOLE, 5,7-DINETHYL- 145 54020-53-0 1065 68.7 INDOLE, 5-NETHYL- 131 614-96-0 1067 INDOLE, 6-NETHYL- 131 3420-02-8 1066 65.7 INDOLE, 7-METHYL- 131 933-67-5 1079 INDOLE, C3-ALKYL-*1 159 1080 INDOLE, C3-ALKYL-*2 159 1081 INDOLE, C3-ALKYL-#3 159 1082 INDOLE, C3-ALKYL-84 159 578 INDOLE, N-METHYL- (SBB240D) 131 603-76-9 1443 INDOLECARBOXALDEHYDE-3 145 487-89-8 1063 INDOLE-1H, 1-ETHYL- 145 10604-59-8 342 1NDOLE-1H, 3-(3-PYRIDYLNETHYL)-2,3-DIHYDRO- 210 78210-52-3 1332 INDOLE-2-ONE, 2,3-DIRYDRO- (OXINDOLE) 133 59-48-3 1331 INDOLINONE-2, 3-ETHYL- 161 15379-45-0 970 INDOLIZINE, 6-METHYL- 131 1761-11-1 321 66.0 INDOLIZIN-8-ONE, 5,6,7,8-TETRANYDRO- (SW1300) 135 54906-44-4 447 IONOL, ALPHA-1-HYDROXY-4-OXO- 226 65017-80-3 (69699-4 445 73.3 IONOL, ALPHA-4-OXO- (SR30D) 208 34318-21-3 446 IONOL ALPHA-DIHYDRO-4-OXO- (SR31D) 210 36151-02-7 1621 76.0 , IONOL, ALPHA-DIHYDRO-4-OXO- (SR31D) 210 36151.-02-7- 58 48.2 IONOL, BETA- 194 27008-60-2 120 43.4 IONONE, ALPHA- 192 6901-97-9 37 47.0 IONONE, BETA- 192 14901-07-6 46 IONONE, BETA-4-OXO- 224 98910-85-1 1619 53.9 IONONE, BETA-DEHYDRO- 190 1203-08-3 159 IONONE, BETA-DEHYDRO- 190 1203-08-3 1583 65.6 IONONE, DERIVATIVE (SEE BOOK FOR STRUCTIIRE) 206 78830-89-4 1552 51.5 IONONE, PSEUDO 192 13927-47-4 1553 55.2 IONONE, PSEUDO (E,E-1SOMER) 192 3548-78-5 1503 41.0 IONONE, TETRAHYDRO- 196 6138-85-8 54 62.5 1SOBENZOFLMUNONE-1(3H) (PHTHALIDE) 134 87-41-2 1240 ISOBUTANETHIOL 90 513-44-0 1299 2.8 ISOBUTYL ANINE 73 78-81-9 2156 2.3 ISOBUTYRALDEHYDE 72 78-84-2 1463 17.5 ISOBUTYRALDEHYDE (PROPANAI, 2-METHYL-) 72 78-84-2 1229 ISOBUTYRAMIDE, N-METHYL- (PROPANANIDE,N,2-DINETHYL-) 101 2675-88-9 2158 5.3 ISOBUTYRONITRILE 69 78-82-0 657 ISOCAPROIC ACID (NETHYLVALERIC-4 ACID) 116 646-07-1 1339 1SOINDOLIN-1-ONE-1H, 2,3-DIHYDRO- 133 480-91-1 358 ISOINDOLIN-1-ONE-iH, 2,3-DIHYDRO-3-METHYL- 147 NO 8 GIVEN 75 36.4 ISOPHORONE, 4-0X0- (SR55C) 152 1125-21-9 1656 36.4 ISOPHORONE, 4-OXO- (SR55C) 152 1125-21-9 504 iS00UINOLINE 129 119-65-3 971 ISOOUINOLINE, 1,2,3,4-TETRANYDRO- 133 91-21-4 1313 ISOQUINOLINE, 1-AMINO- 144 1532-84-9 505 ISOOUINOLINE, 1-METHYL- (SBB210D) 143 1721-93-3 973 ISOCUINOLINE, 1-METHYL-1,2,3,4-TETRAHYDRO- 147 4965-09-7 509 ISOQUINOLINE, 1-n-BUTYL- (SB8244D) 185 7661-38-3 506 ISOGUINOLINE, 3-METHYL- (SBB209D) 143 1125-80-0 972 ISOGUINOLINE, 5,6,7,8-TETRANYDRO- 133 36556-06-6 507 ISOCUINOLINE, ?-METHYL- (SBB2550) 143 508 ISOGUINOLINE, ?-NETHYL-, (SBB2560) 143. 1241 ISOTHIAZOLE 85 288-16-4 1899 6.0 ISOVALERIC ACID, NETHYL ESTER 116 556-24-1 1367 ISOXAZOLE, 3,4,5-TRIHETHYL- 111 10557-82-1 1164 ISOXAZOLE, 3,4,5-TRIMETHYL- 111 10557-82-1 907 16.2 43.5 1SOXAZOLE, 3,5-DINETHYL- 97 300-87-8 1911 12.7 ISOXAZOLE, 5-METHYL- 83 5765-44-6 14 57.5 Ka COMPOUND 190 15 Kb COMPOUND 190 16 Kc COMPOUND 190 17 61.1 Kd COMPOUND 190 Ln 155 K-4 (ISOMER OF SR48C) 198 N 732 LEVOGLUCOSAN mono-ACETATE 204 61891-55-2 m 199 24 9 , LINALOOL OXIDE 01 170 71635-17-1 N 198 . 26.3 LINALOOL OXIDE 92 170 a% 361 LOLIOLIDE (SM130C) 196 5989-02-6 U) Oo N Ob 33

TOBACCO.WK1 Retention Time Database - Septeiaber 5, 1989 Sorted by Coffpound Name RT (min) CMPD ----------- # DBWAX DB1 COMPOUND NAME -- -- --- - ----- ---- ----- --- ----- --- --- -- . .. 693 LOLIOLIDE (SM130C) 1874 29.7 LGNGiFOLINE 1816 50.7 MALTOL, ETHYL- 1749 96.2 MANOYL OXIDE, 12a-HYDROD(Y-13-EPI- (SR9C) 23 62.4 MARIOLIDE 1745 58.2 MARIOLIDE, DIHYDRO- (SR58C) 2067 36.0 75.7 MENTHOL, ISO- 2086 47.2 82.4 MENTH-I-ENE-9-OL, para- 2087 38.1 77.0 MENTH-B-EN-2-OL (DIHYDROCARVEOL) 1466 18.2 METHACROLEIN 659 METHACRYLIC ACID 2146 3.2 6.3 METHANOL 297 54.8 METHANONE, CYCLOPROPYL-3-PYRIDYL- (SNN1160) 1798 66.9 102.6 METHANONE, DIPHENYL- (BENZOPNENONE) 1284 METHYL AM1NE 1283 METHYL AMINE, N,N-DIMETHYL- 1285 METHYL ANINE, N-METHYL- 1811 31.3 METHYLAMINE, N,N-DIACETYL- (ACETAMIDE,N-ACETYL-N-METHYL-) 2147 3.6 15.9 METHYLENE CHLORIDE 1158 METHYLENEDIOXYBENZENE-1,2, 5-ALLYL-3-METHOD(Y- 41 M11-Va 42 MII-Vb 43 MII-Vc 10 57.4 90.8 MYOSNINE 974 MYOSMINE, 41-METHYL- 975 MYOSMINE, 58-NETHYL- 1873 59.0 MYRISTICIN, (from nutmeg) 1286 NAPHTHALENAMINE-1 1287 NAPHTHALENAMINE-1, N-PHENYL- 1288 NAPHTHALENAMINE-2, N-PHENYL- 230 38.2 NAPHTHALENE 1854 27.6 NAPHTHALENE, 1,2,3,4-TERANYDRO- (TETRALIN) 1877 36.7 NAPHTHALENE, 1,2,3,5,6,7,8,8a-OCTAHYDRO-7-(1-NETHYLETHENYU- (VALENCENE) 229 44.2 84.8 NAPHTHALENE, 1-METHYL- 1837 68.6 NAPHTHALENE, 2-ACETYL- 1684 68.4 NAPHTHALENE, 2-NYDR00(Y-1-00(0-4,4,7-TRIMETHYL-1,4-DIHYDRO- 1853 9.9 NAPHTHALENE, DECAHYDRO- (DECALIN) 33 66.0 NAPHTHALENOL-1, 1,2,3,4-TETRAHYDRO-4,5,8-TRIMETHYL- 1591 66.2 NAPHTHALENOL-1, 1,2,3,4-TETRAHYDRO-4,5,8-TRIMETHYL-, ISOMER (SR238C) 1847 89.3 NAPHTNALENOL-2 976 NAPHTHYRIDINE-1,5 550 NAPHTHYRIDINE-1,5, 3-METHYL- (566267D) 549 NAPHTHYRIDINE-1,6, 3-METHYL- (SBB168D) 314 NAPHTHYRIDINE-1,8, 3-BUTYRYL- (SW134D) 622 NAPHTHYRIDINE-1,8, 3-METHYL- (SBB266D) 2098 51.0 94.6 NAPTHALENE, 1,2-DIMETHYL- 2099 48.7 91.7 NAPTHALENE, 1,3-DiMETHYL- 2100 50.1 93.4 NAPTHALENE, 1,4-DIMETNYL- 2101 48.8 92.0 NAPTHALENE, 1,6-DIMETHYL- 2102 53.3 NAPTHALENE, 1,8-DIMETHYL- 2103 47.3 90.7 NAPTHALENE, 2,6-DIMETHYL- 2104 47.3 90.7 NAPTHALENE, 2,7-DIMETHYL- 2097 43.1 83.8 NAPTHALENE, 2-METHYL- 1756 52.2 NEROLIDOL ACETATE, (cis) 1755 50.0 NEROLIDOL ACETATE, (trans) 573 NICOTELLINE 759 NICOTINANIDE 372 NICOTINAMIDE, 2,4-DIMETHYL- 326 NICOTINAMIDE, 2,6-DIMETHYL- (SWW177D) 432 NICOTiNAMIDE, 2-METHYL- (SYN218D) 411 NICOTINAMIDE, 4-ETHYL- (S{Ar241D) 423 NICOTINAMIDE, 6-ETHYL- (516227D) 1340 NICDTINAMIDE, 6-METHYL- 250 88.4 NICOTINAMIDE, N-METHYL- (SWW270) 236 44.3 86.8 NICOTINE 7 44.3 86.8 NICOTINE 977 NICOTINE, 2',31-DENYDRO- (ISONICOTEINE) 873 NICOTINE, 2-HYDROXY- (SL29D) 1306 NICOTINE, ALPHA-AMINO- 874 NICOTINE, ISOMER (SL19D) 877 NICOTINE, ?-HYDROXY- MY CAS NUlBER . 196 5989-02-6 -- 204 475-20-7 140 4940-11-8 302 180 15356-74-8 182 10547-84-9 154 23283-97-8 154 13835-30-8 154 619-01-2 70 78-85-3 86 79-41-4 32 65-57-1 147 24966-13-0 182 119-61-9 31 74-89-5 59 75-50-3 45 124-40-3 115 1113-68-4 85 75-09-2 192 18312-21-5 306 306 306 146 532-12-7 160 78210-37-4 160 192 607-91-0 143 - 134-32-7 219 90-30-2 219 135-88-6 128 91-20-3 132 119-64-2 204 4630-07-3 142 90-12-0 170 93-08-3 202 S7601-69-1 138 91-17-8 190 190 144 135-19-3 130 254-79-5 144 18937-71-8 144 14757-43-8 200 144 14759-22-9 1W -573-98-8 156 575-41-7 156 571-58-4 156 575-43-9 156 569-41-5 156 581-42-0 156 582-16-1 142 91-57-6 264 264 233 494-04-2 122 98-92-0 150 72692-96-7 150 10131-48-3 136 S8539-65-4 150 78210-59-0 150 78210-60-3 136 6960-22-1 136 114-33-0 162 54-11-S 162 54-11-5 160 525-74-6 178 25110-79-6 177 204 178 34

TOBACCO.YK1 Retention Time Database - Septeaben S, 1989 Sorted by Conpoud Name RT (min) CMPD ----------- S DBWAX DB1 CONPOl1ND NAME ----- ----- -•--------------------------------- -------------------- --- ---• ----- 536 61.9 NICOTYRINE, BETA- 2162 47.4 NONADECANE 1434 22.0 67.9 NONANAL 1955 3.4 53.3 NONANE 1444 36.9 NONANE-2,4-OIENAL 1446 NONANE-2,4-DIENAL, 6-METHYI- (SR137C) 1445 NONANE-2,4-DIENAL, 6-METHYL- (SR154C) (ISOMER OF SR137C) 1447 NONANE-2,6-DIENAL 1773 39.8 NONANE-2,6-DIEN-1-OL 1903 63.5 NONANE-4,6-DIENOIC ACID 129 NONANOIC ACID 1833 75.3 NONANOIC ACID, 4-OXO- 131 27.4 NaNANOIC ACID, NETHYL ESTER 1771 35.8 73.2 NOHANOL-1 1867 35.8 73.2 NONANOL-1 2085 28.7 67.7 NONANOL-2 1875 27.8 NONANOL-3 1733 22.3 67.1 NONANONE-2 188 59.6 NONA-2,5,8-TRIONE 1617 45.4 NONA-6,8-DIEN-2-OL, [R-(E)]-B-NETHYL-S-(1-METHYLETHYL)- (SOLANOL) 6 38.3 NONA-6,8-D1EN-2-ONE, [R-(E)]-8-METHYl-S-(1-NETHYLEHTYL)- (SOLANONE) 1946 3.9 52.3 NONENE-1 1448 NON-2-ENAL 1878 67.7 NOOKATONE 1819 60.0 NORAMBRENOLIDE ETHER 1942 36.2 NORBORNYLENE 781 NORCOTININE-3 (SL260) 1016 NORNICOTINE 978 NORNICOTINE, 1-BUTYL- 1508 52.8 NORNICOTINE, 1-PENTYL- 979 NORNICOTINE, 1-PENTYL- 343 NORNICOTINE, NO-(5-NETHYL-2-FURANYNETHYL)- (SW1900) 18 NORNICOTINE, N-ACETYL- 760 NORNICOTINE, N-ACETYL- 878 46.9 NORNICOTINE, N-ETHYL- (SL39D) 761 NORNICOTINE, N-FORMYL- 13 NORNICOTINE, N-FORMYL- 300 NORNICOTINE, N-FURAIIYLMETHYL- (SW1170) 1013 NORNiCOTiNE, N-NITROSO- 337 NORNICOTINE, N-(1-OXOBUTYI)- (SW84D) 1598 98.4 NORNICOTINE, N-(1-OD(OBUTYL)- (SW84D) 273 NORNICOTINE, N-(1-OD(OOCTYL)- (SWH1O50) 346 NORNICOTINE, N-(FURAIIYLETHYU- (SW187D) 980 NORNICOTYRINE, 1-(5-PROPYL-2-FiXtANYL)- (SYY87D) (SEE /1015) 2132 79.0 OCTACOSANE 2161 42.9 OCTADECANE 2139 67.8 OCTADECANOIC ACID, ETHYL ESTER (STEARIC ACID, ETHYL ESTER) 1735 67.0 OCTADECANOIC ACID, METHYI ESTER (STEARIC ACID, METHYL ESTER) 1818 71.5 OCTADECANOL -1 2141 69.9 OCTADECA-9,12-DIENOIC AC1D, ETHYL ESTER (IINOLEIC ACID, ETHYL ESTER) 1736 66.4 OCTADEC-9-EN-OIC ACID (Z), METHYL ESTER (OLEIC ACID, I4ETHYL ESTER) 1870 113.6 OCTADEC-9-EN-OIC ACID (Z) (OLEIC ACID) 1435 16.7 60.0 OCTANAL 1451 OCTANAL, 2,7-DINETHYL-7-NYDROD(Y- 1450 OCTANAL, 3,7-DiNETHYL-7-HYDROXY- 1289 OCTANANINE 1956 2.2 44.3 OCTANE 2017 28.4 65.9 OCTANENITRiLE 1558 18.5 OCTANE-2,3-DIONE 183 OCTANE-2,3-DIONE 1449 OCTANE-2,6-DIENAL, 3,7-D UETHYL-, (NERAL OR Z-CITRAL) 128 OCTANOIC ACID 1539 24.1 OCTANOIC ACID, ETHYL ESTER 2 OCTANOIC ACID, IIETHYL ESTER 3 OCTANOIC ACID, METHYL ESTER 4 OCTANOIC ACID, METHYL ESTER 1 OCTANOIC ACID, METHYL ESTER 1546 30.8 65.8 OCTANOL-1 1781 35.9 OCTANOL-1, 3,7-DINETHYL- (TETRAHYDROGERANIOL) 1795 35.9 OCTANOL-1, 3,7-OIMETHYL- (TETRAHYDROGERANIOL) 1686 24.2 OCTANOL-2 MW 158 487-19-4 268 629-92-5 142 124-19-6 128 111-84-2 138 6750-03-4 137 152 138 26370-28-5 140 7M-44-9 154 1S8 112-05-0 172 6064-52-4 172 1731-84-6 144 143-08-8 144 143-08-8 144 628-99-9 144 624-51-1 142 821-5S-6 170 38284-28-5 196 40525-38-0 194 1937-54-8 126 124-11-8 140 2463-53-8 218 4674-50-4 236 6790-58-5 94 498•66-8 162 5980-06-3 148 494-97-3 204 218 218 242 78210-86-3 190 S979-94-2 190 5979-94-2 176 5979-92-0 176 38840-03-8 176 38840-03-8 228 78210-85-2 177 a6543-55-8 218 69730-91-2 218 69730-91-2 274 38854-10-3 242 78210-87-4 252 78210-89-6 394 630-02-4 254 593-45-3 312 298 112-61-8 234 112-92-5 308 544-35-4 296 112-62-9 282 112-80-1 128 124-13-0 172 172 107-75-5 129 111-86-4 114 111-65-9 125 124-12-9 142 585-25-1 142 585-25-1 152 106-26-3 144 124-07-2 172 106-32-1 158 111-11-5 158 111-11-5 158 111-11-5 158 111-11-5 130 111-87-5 158 - 106-21-8 158 106-21-8 130 123-96-6 CAS NtlFIBER 35

TOBACCO.WK1 Retention Time Database - Septeaber 5, 1989 Sorted by Compound Nam RT (min) CMPD ----------- * DBWAX DB1 COMPOUND NAME ---- ----- ----- ----------------------------------------------------------------------- 190 24.5 OCTANOL-3, 3,7-DIMETHYL-, (TETRAHYDROLINALOOL) 1822 23.1 OCTANOL-3 (DL) 1734 17.1 59.1 OCTANONE-2 1960 55.2 OCTANONE-3 169 30.1 OCTA-1,6-DIEN-3-OL, 3,7-DIMETHYL- (LINALOOL) 1556 30.1 OCTA-1,6-DIEN-3-0L, 3,7-DIMETHYL- (LINALOOL) 193 OCTA-2,6-DIEN-1-OL, 3,7-DIMETHYL- (GERANIOL, trans-) 1554 44.0 OCTA-2,6-DIEN-I-OL, 3,7-DIMETNYL- (trans-GERANIOL) 1774 40.5 OCTA-2,6-DIEN-I-OL, cis-3,7-DIMETNYL- (NEROL) 1728 39.7 OCTA-2,6-DIEN-1-OXYACETATE, 3,7-DINETHYL- (GERANYL ACETATE) 165 39.7 OCTA-2,6-DIEN-1-OXYACETATE, 3,7-DINETHYL- (GERANYL ACETATE) 182 OCTA-2,7-DIENE, 2-METHYL-6-METNYLENE- (NYRCENE) 1741 69.0 OCTA-9,10-DECENOIC ACID, METHYL ESTER (LINOLEIC ACID, METHYL ESTER) 1945 2.5 43.1 OCTENE-1 1881 25.0 OCT-I-EN-3-0L 1452 OCT-2-ENAL, 2-PROPYL- 1569 22.7 OCT-3-EN-2-ONE 1453 OCT-6-ENAL, 3,7-DINETHYL- (CITRONELLAL) 1901 40.2 OCT-6-EN-1-OL, 3,7-DIMETHYL- (CITRONELLOL) 317 56.5 OXAZINE-1,2, 2-METHYL-6-(3-PYRIDYL)-3,4,5,6-TETRAHYDRO- 1341 OXAZINE-1,2(2H), 3-(1-METHYLETHYL)-6-(3-PYRIDINYL)-TETRANYDRO-, (SR161D) 303 0XAZ1NE-1,2(2H), 3-(1-METHYLETHYL)-6-(3-PYRIDINYL)-TETRAHYDRO-, (SW161D) 1129 OXAZINE-1,4, TETRAHYDRO-2H- (NORPHOLINE) 1925 14.7 OXAZINE-1,4, TETRAHYDRO-2H- (MORPHOLINE) 1928 5.7 OXAZOLE 903 12.7 OXAZOLE, 2,4,5-TRIMETHYL- 905 OXAZOLE, 2,4-DIMETHYL- 895 OXAZOLE, 2,4-DIMETHYL-S-ETHYL- 623 OXAZOLE, 2,5-DIMETHYL- 899 OXAZOLE, 2-ETHYL-4-METHYL- 898 OXAZOLE, 2-ETHYL-S-METHYL- 906 OXAZOLE, 4,5-OIMETHYL- 896 OXAZOLE, 4,5-DIMETHYL-2-ETHYL- 904 OXAZOLE, 4-ETHYL-2-METHYL- 901 OXA20LE, 4-ETHYL-S-METHYL- 902 OXAZOLE, 5-ETHYL-2-METHYL- 900 OXAZOLE, 5-ETHYL-4-METHYL- 897 OXAZOLE, 5-METHYL-2-PROPYL- 1725 73.6 OXA20LIDINE-2,4-DIONE, 5-METHYL- 935 OXAZOLIDINE-2,4-DIONE, (SR119D) 1895 63.4 OXAZOLIDIN-2-ONE, 4,5-DIMETHYL- (ISOMER AT 66.5 KIN D8W1X) 1649 24.8 OXIRANEMETHANOL, ACETATE (GLYCIDOL, ACETATE) 1739 26.1 OXIRANEMETHANOL (GLYCIDOL) 234 55.8 OXYSOLANONE 2205 69.7 PENTACOSANE 1454 PENTADECANAL 1949 29.5 PENTADECANE 2089 61.4 PENTADECANOL-1 1828 62.4 PENTADECA-5,9,13-TR1EN-2-ONE, 6,10,14-TRIMETHYL- (FARNESOL ACETONE) 2193 2.1 28.3 PENTADIENE-1,3, 3-METHYL- 2194 2.2 28.9 PENTADIENE-1,3, 3-METHYL- (cis or trans) 1456 5.3 PENTANAL, 2-METHYL- (VALERALDEHYDE, 2-METHYL-) 1455 6.2 31.6 PENTANAL (VALERALDEHYDE) 1869 6.2 31.6 PENTANAL (VALERALDEHYDE) 758 PENTANAMIDE 377 PENTANAMIDE 378 PENTANAMIDE, 3-METHYL- (VALERANIDE, 3-METNYL-) 379 53.2 PENTANAMIDE, 4-METHYL- (VALERAMIDE,4-METHYL-) 356 PENTANAMiDE, N-ETHYL- (VALERAMIDE, N-ETHYL-) (SWAW194D) 1290 PENTANAMINE-1 1291 PENTANAMINE-2 1292 PENTANAMINE-3 2201 14.8 PENTANENITRILE, 4-METHYL- 2157 12.4 PENTANENITRILE (VALERONITRILE) 392 38.1 PENTANENITRILE (VALERONITRILE) 1983 38.1 PENTANENiTR1LE (VALERONITRILE) 1972 26.9 PENTANE-1,3-DIENE, 2-METHYL- 1999 28.3 PENTANE-1,3-DIENE, 3-METHYL- 1998 27.7 PENTANE-1,3-DIENE, 3-METHYL- (isaoer of *1999) 1637 43.4 PENTANE-1,3-DIOL 820 60.5 PENTANE-1,4-DIONE, 1-(2-FtNtANYLMETHYL)- (SR1370) NW CAS NIMBER -158 57106-88-4 130 20296-29-1 128 111-13-7 128 106-68-3 154 78-70-6 154 78-70-6 154 106-24-1 154 106-24-1 154 106-25-2 196 16409-44-2 196 16409-44-2 136 123-35-3 308 112-63-0 112 111-66-0 128 3391-86-4 168 7373T-28-5 126 1669-44-9 154 106-23-0 156 106-22-9 178 15769-88-7 206 71607-95-9 206 71607-95-9 87 110-91-8 87 110-91-8 69 288-42-6 111 20662-84-4 97 7208-05-1 125 33318-74-0 97 23012-11-5 111 24667-03-6 111 42463-54-7 97 20662-83-3 125 S3833-30-0 111 S3833-20-8 111 S3833-28-6 111 53833-29-7 111 29584-92-7 125 S3833-31-1 115 27770-23-6 101 2346-26-1 11S 58628-98-1 116 6387-89-9 74 S56-S2-S 196 3S953-21-0 352 629-99-2 226 2765-11-9 212 629-62-9 228 629-76-S 262 762-29-8 82 4549-74-0 82 4549-74-0 100 123-1S-9 86 110-62-3 86 110-62-3 101 626-97-1 101 626-97-1 115 61892-69-1 115 1119-29-5 129 S4007-33-9 87 110-58-7 87 625-30-9 87 616-24-0 97 542-54-1 83 110-59-8 83 110-59-8 83 110-59-8 82 1118-58-7 82 2787-43-1 82 2787-45-3 104 3174-67-2 166 52786-29-5 ; 36

TOBACCO.YK1 Retention Time Database - Septamber 5, 1989 Sorted by Ccapourd Name RT (min) CMPD ----------- # DBWAX DB1 COMPOUND NAME MY CAS NUMBER ---- ----- ----- -------------------------------------------------------------------- --- 1293 PENTANE-1,5-DIAMINE 102 462-94-2 1350 6.9 31.0 PENTANE-2,3-D10NE 100 600-14-6 850 PENTANE-2,4-DIOL, 2-METHYL- (SR28D) 118 107-41-5 125 PENTANOIC ACID 102 109-52-4 123 PENTANOIC ACID, 2-METHYL- 116 97-61-0 241 PENTANOIC ACID, 2-METHYL-4-OD(0- (SW9D) 130 6641-83-4 660 PENTANOIC ACID, 2-METHYL-4-OX0- (SW9D) 130 6641-83-4 36 41.9 54.4 PENTANOIC ACID, 3-METHYL- 116 105-43-1 1666 62.9 PENTANOIC ACID, 3-METHYL-4-OH0- 130 6628-79-1 109 61.8 PENTANOIC ACID, 4-0X0- (LEVULINIC ACID) 116 123-76-2 1865 15.5 38.8 PENTANOL-1 88 71-41-0 2073 17.9 45.5 PENTANOL-1, 2-METHYL- 102 105-30-6 2074 19.1 46.6 PENTANOL-1, 3-METHYL- 102 S89-35-5 2075 18.3 45.8 PENTANOL-1, 4-METHYL- 102 626-89-1 2044 10.0 32.1 PENTANOL-2 88 6032-29-7 2076 8 7 36 0 PENTANOI-2 2-METHYL- 102 S90-36-3 2077 . 12.5 . , 41.4 PENTANOL-2, 3-METHYL- 102 565-60-6 1939 12.0 38.3 PENTANOL-2, 4-METHYL- 102 108-11-2 2079 10.9 40.0 PENTANOL-3, 2-METHYL- 102 565-67-3 2120 31.5 50.6 PENTANONE, 2,5-HYDROXY- 102 1071-73-4 467 4.8 30.4 PENTANONE-2 86 107-87-9 471 PENTANONE-2, 4-HYDROXY-4-METHYL- (DIACETONE ALCOHOL) 116 123-42-2 468 6.2 36.0 PENTANONE-2, 4-METHYL- 100 108-10-1 1705 36.3 PENTANONE-2, 5-HYDROXY-, ACETATE 144 5185-97-7 1961 31.4 PENTANONE-3 86 96-22-0 2107 15.4 PENTA-1,3-DIENE (PIPERYLENE) 68 504-60-9 2111 20.4 PENTA-1 4-D1ENE, 2-METHYL- 82 763-30-4 1995 , 20.1 PENTA-1,4-DIENE, 2-METHYL- 82 763-30-4 2110 1.6 17.6 PENTA-I,4-DIENE, 3-METHYL- 84 1115-08-8 762 PENTENAMIDE-2 99 15856-96-9 1342 PENTENAMIDE-2, N-METHYL- 113 1343 PENTENAMIDE-3, 4-METHYL- 113 70265-05-3 2172 1.4 12.6 PENTENE-1 70 109-67-1 1768 11.9 PENTENE-1, 3-HYDROXY- 86 616-25-1 2106 19.0 PENTENE-1, 3-METHYL- 84 922-61-2 2105 18.8 PENTENE-1, 4-METHYL- 84 . 691-37-2 2109 1.6 24.2 PENTENE-2, 2-METHYL- 84 625-27-4 2121 25.1 PENTENE-2, 3-METHYL- (cis or trans) 84 922-61-2 2122 26.1 PENTENE-2, 3-METHYL- (trans or cis) 84 922-61-2 1459 10.9 46.0 PENT-2-ENAL, 2-METHYL- 98 623-36-9 1457 PENT-2-ENAL, trans 84 1576-87-0 214 PENT-2-ENOIC ACID, 2-METHYL- 114 3142-72-1 1658 47.2 PENT-2-ENOIC ACID, 2-METHYL- 114 3142-72-1 1458 PENT-3-ENAL, cis 84 53448-06-9 1713 46.8 PENT-3-ENAMIDE, N-METHYL- 113 661 43.5 PENT-3-ENOIC ACID 100 33698-87-2 470 10.0 30.4 PENT-3-EN-2-ONE 84 3102-33-8 1460 PENT-4-ENAL, 2-METHYL- 98 3973-43-1 1338 PHATHALIMIDE, 4,6-D11¢THYL- 175.17100-62-8 1880 10.4 PHELLANDRENE-a 136 4221-98-1 1189 PHENANTHRIDINE 179 229-87-8 481 49.7 PHENOL 94 108-95-2 146 57.7 80.5 PHENOL, 2,3,5-TRIMETHYL- 136 697-82-5 2021 52.1 78.5 PHENOL, 2,3,6-TRIMETHYL- 136 2416-94-6 1802 53.4 PHENOL, 2,3-DIMETHOXY- 154 5150-42-S 140 55.5 PHENOL, 2,3-DIMETHYL- 122 S26-75-0 2026 50.5 75.5 PHENOL, 2,4,6-TRIMETHYL- 136 S27-60-6 141 53.0 PHENOL, 2,4-DIHETHYL- 122 105-67-9 142 52.8 PHENOL, 2,5-DIMETHYI- 122 95-87-4 953 45.4 PHENOL, 2,6-BIS(1,1-DIMETHYLETHYU-4-METNYL- 220 128-37-0 2209 47.1 95.4 PHENOL, 2,6-bis(1,1-DIMETHYLETHYL)-4-METHYL- (BHT) 220 128-37-0 78 60.0 PHENOL, 2,6-DiNETHOHY- 154 91-10-1 143 45.9 PHENOL, 2,6-DIMETHYL- 122 576-26-1 2138 44.0 60.4 PHENOL, 2-CHLORO- 128 95-57-8 147 52.8 PHENOL, 2-ETHYL- 122 90-00-6 958 PHENOL, 2-ETHYL-6-METHYL- 136 1687-64-S 117 44.0 PHENOL, 2-METHOXY- (GUAIACOL) 124 90-05-1 957 PHENOL, 2-METHOXY-4-METHYL- (4-METHYLOU111ACOL) 138 93-51-6 1856 62.0 PHENOL, 2-METH00(Y-4-(1-PROPENYL)- (Et1GENOL, iso-) 164 97-54-1 1792 56.4 (EUGENOL) PHENOL, 2-METHOI(Y-4-(2-PROPENYL)- 164 97-53-0 130 49.6 . PHENOL, 2-METHYL- 108 95-48-7 37

TOBACCO.WK1 Retention Time Databaae - SepteaibeP 5, 1989 Sorted by Campo1I1d Name RT (min) CMPD ----------- ! DBWAX DB1 COMPOll11D NAME MW CAS NUMBER ---- ----- ----- ------------------------------------------------•------------------- --- •-•--------•- 1696 71.7 2-PHENYL- PHENOL 170 90-43-7 1842 54.8 , PHENOL, 2-PROPYL- 136 6i4-35-9 2208 69.7 92.6 PHENOL, 2-(1,1-DINETHYLETHYL)-4-METHOD(Y- (BNA) 180 25013-16-5 139 53.6 PHENOL, 2-(1-METBYLETNYL)- 136 88-69-7 1766 57.4 PBENOL, 2-(1-METHYLETNYL)-S-METHYL- (THYMOL) 150 09-83-8 94 56.0 PHENOL, 2-(2-PROPENYL)- 134 1745-81-9 1981 64.3 82.9 PHENOL, 3,4,5-TRIMETHYL- 136 527-54-8 2134 77.5 88.0 PHENOL, 3,4-Dl1ETNONY- 154 2033-89-8 1801 78.5 PHENOL, 3,4-DIMETNOD(Y- 154 2033-89-8 144 58.4 PHENOL, 3,4-DIMETBYL- 122 95-65-8 1800 84.3 PHENOL, 3,5-DIMETNOD(ri 154 500-99-2 145 56.7 PHENOL, 3,5-DIMETBYL- 122 108-68-9 137 52.6 PHENOL, 3-METNYL- 108 108-39-4 408 PHENOL, 3-PHENOD(Y- (SlIlR44D) 186 713-68-8 722 PHENOL, 4-ACETOXY- (HYDROGUINONE, MONACETATE) (SR1200) 152 3233-32-7 148 56.8 PHENOL, 4-ETHYL- 122 123-07-9 1719 51.0 PHENOL, 4-ETHYL-2-METHOXY- (GUTAICOL, 4-ETNYL-) 152 2785-89-9 138 52.4 PHENOL, 4-METHYL- 108 106-44•S 1826 59.6 PHENOL, S-ET8YL-2-NETHYL- 136 1687-65-6 1410 PHENYLACETALDEHYDE, alpha-(2-fURANMETHYLENE)- 198 1409 34.2 PHENYLACETALDEHYDE (SR52C) 120 122-78-1 763 PHENYLACETAMIDE (BEN2ENEACETAMIDE) 135 103-81-1 1541 40.3 PHENYLACETIC ACID, ETHYL ESTER (BENZENEACETIC ACiD, ETHYL ESTER) 164 101-97-3 1571 39.5 PHENYLACETIC ACID, METHYL ESTER (BEN2ENEACETIC, METHYL ESTER) 150 101-41-7 662 69.3 PHENYLACETIC ACID (BENZENEACETIC ACID) 136 103-82-2 1922 70.0 PHENYLENEOIAMINE-1,2, 4,5-DIMETHYL- 136 3171-45-7 1919 62.7 PHENYLENEDIAMINE-1,2 (BENZENEOIAMINE-1,2) 108 95-S4-S 1921 72.5 PHENYLENEDiAMINE-1,3, 4-METHYL- 122 95-80-7 26 46.3 69.2 PHENYLETHYL ALCOHOL (BEN2ENEETHANOL) 122 60-12-8 735 75.3 PHTHALIC ACID, DIBUTYL ESTER 278 84-74-2 734 PHTHALIC ACID, DIETHYL ESTER 222 84-66-2 736 PHTHALIC ACID, DIPROPYL ESTER 250 131-16-8 737 PHTHALIC ACID, DI-(2-ETHYL)-HEXYL ESTER 390 117-81-7 1841 62.5 PHTHALIDE (IS08EN20flNGNONE-1(3N)) 124 87-41-2 1580 73.9 PHTHALIMIDE, 4,6-OIMETHYL- (1SOINDOLE-1H, 4,6-DIMETNYL-) 175 1337 PHTHALIMIDE, 4,7-DIMETNYL- (1SOINDOLE-1N, 4,7-DINETHYL-) 17S 1SS40-88-2 1334 87.3 PHTHALIMIDE, 4-METBYL- (ISOINDOLE-1N, 4-METHYL-) 161 7251-82-3 1335 96.7 PHTHALIMIDE, 5-METHYL- (ISOINDOLE-1N, 5-METHYL-) 161 40314-06-S 1333 PHTHALIMIDE, N-METHYL- (1SOINDOLE-1N, N-METHYL-) 161 S50•44-7 1336 PHTHALIMIDE (ISOINDOLE-1N, 1,3-DlONE-2H) 147 85-41-6 782 94 0 PHTHALIMIDINE 133 480-91-1 1507 . 54.6 PHYTONE 268 S02-69-2 428 64.8 PICOLINAMIDE-2 (PYRIDINECARBOXAMIDE-2) (SlA2200) 122 14S2-77-3 1132 PIPERAZINE, 1,2-DIMETHYL- 114 2S0S7-77-6 1130 8.7 PIPERAZINE, 1,4-DIMETHYL- 114 106-58-1 1133 15.0 PIPERAZINE, 1-METIIYL- 100 109-01-3 1 31 20 8 5 THY 2 - 114 106-55-8 1 1134 . 21.1 -DIME PIPERAZINE, , L PIPERAZINE, 2-METBYL- 100 109-07-9 1135 21.1 PIPERAZINE, 2-METHYL- 100 109-07-9 1226 PIPERAZINE-2,5-DIONE 114 106-57-0 266 72.4 PIPERAZINE-2,5-DIONE, 1,4-DIMETHYL- (SW65) 142 S076-82-4 252 PIPERAZiNE-2,5-D10NE, 3,4-PYRROLO(1,2-A)- (SW34D) 168 19943-28-3 788 PIPERAZINE-2,5-DIONE, 3-ALLYL- (SL160) 154 61892-78-2 1208 7.3 39.5 PIPERIDINE 85 110-89-4 1136 PIPERIDINE, 1-ETHYL- 113 764-09-6 1143 3.6 40.0 PIPERIDINE, 1-METHYL- 99 626-67-5 1145 PIPERIDINE, 1-NITROSO- 114 100-75-4 1139 PIPERIDINE, 2,3-DIMETHYL- 113 5347-68-2 1138 6.5 47.1 PIPERIDINE, 2,6-DINETHYL- 113 504-03-0 1926 6.5 47.1 PIPERIDINE, 2,6-DIMETHYL- 113 504-03-0 1137 PIPERIDINE, 2-ETHYL- 113 1484-80-6 1908 6.9 43.0 PIPERIDINE, 2-METHYL- 98 109-05-7 1144 PIPERIDINE, 3,4-DEHYDRO- 83 694-05-3 1140 PIPERIDINE, 3,4-DEHYDRO-i-ETNYL- 111 6972-40-3 2045 11.1 51.4 PIPERIDINE, 3,5-DIMETNYL- 113 35794-11-7 1141 46.6 PIPERIDINE, 3-METHYL- 99 626-56-2 1142 8.7 45.4 PIPERIDINE, 4-METHYL- 99 626•58-4 767 PIPERIDINE-2,6-DIONE, 3-NETHOD(Y- (GLUTARiMIDE,3-METH00(Y-) 143 v' 768 PIPERIDINE-2,6-DIONE, 3-METHYL- (GLUTARINIDE,3-METHYL-) 127 295S3-S1•3 ' ~ 769 PIPERIDINE-2,6-DIONE, 4-METHYL- (GLUTARIMIDE, 4-METHYL-) 127 25077-26-3 , ~ 766 62.2 PIPERIDINE-2,6-DIONE (GLUTARINIDE) 113 1121-89-7 3 8 t°

I TOBACCO.WK1 Retention Time Database - September 5, 1989 Sorted by Caspand Name RT (min) CMPD ----------- S DBWAX DB1 COMPOUND NANE NIW CAS NIMBER ---- ----- ----- -------------------------------------------------------------------- --- ---- ------------- 786 42.6 PIPERIDONE-2, 1-METNYL- (S124C) 113 931-20-4 784 57.8 PIPERIDONE-2, 3,4-DENYDRO- (SR62D) 97 6052-73-9 785 58.7 PIPERIDONE-2, 4,5-DENYDRO- (SR198D) 97 61892-77-1 783 PIPERIDONE-2, 6-ACETYL-5,6-DENYDRO- (SNN113D) 139 61892-76-0 787 PIPERiDONE-2, 6-METHYL- 113 3279-76-3 1917 23.6 PIPERIDONE-4, 1-NETBYL- 113 1445-73-4 1892 PIPERIZINE-2,5-DIONE, 3,5-DINETHYL- 142 5625-46-7 1461 2.1 11.7 PROPANAL 58 123-38-6 1971 2.1 11.7 PROPANAL 58 123-38-6 1462 PROPANAL, 2,2-DINETNYL- 86 630-19-3 799 34.4 PROPANAL, 2-OXO- (PYRWALDEHYDE) 72 78-98-8 1464 PROPANAL, 3-METNYLTHIO- 104 3268-49-3 2090 2.3 17.5 PROPANAL,2-METHYL- (ISOBUTYRALDEHYDE) 72 78-84-2 370 PROPANANIDE, 2-NETHYL- (ISOBUTYRANIDE) 87 563-83-7 765 PROPANAMIDE, 2-OXO- (PYRWANIDE) 87 631-66-3 1641 35.2 PROPANANIDE, N,2-DINETNYL- (ISOBUTYRAMIDE, N-METNYL-) 101 2673-88-9 1296 PROPANANINE, N,2-DINETHYL- 87 625-43-4 1297 PROPANANINE, N,2-DINETHYL-N-NITROSO- 116 2504-18-9 1298 PROPANAMINE, N-ETNYL-N-NITROSO- 116 16339-04-1 1305 PROPANAIIINE, N-METHYL- 73 627-35-0 1294 PROPANANINE-1 59 107-10-8 1295 PROPANANINE-1, N-ETHYL- 87 20193-20-8 1300 PROPANANINE-1, N-PROPYL- 101 142-84-7 1303 PROPANANINE-2, N-(1-NETHYLETHYL)- 101 108-18-9 1243 PROPANE, 1,11-THIOBIS- (DIPROPYL SULFIDE) 118 111-47-7 2167 3.6 33.0 PROPANE, 1,2-DIMETHOXY- 104 7778-85-0 2114 2.4 28.4 PROPANE, 2,2-DIMETHOXY- 104 77-76-9 2012 34.5 PROPANE, 2-NITRO- 89 79-46-9 373 43.0 PROPANEAMIDE 73 79-05-0 286 PROPANEANIDE, 3-CYANO- (SiA169D) 98 61892-68-0 1323 86.2 PROPANEAMIDE, 3-PHENYL- (SR164D) 149 102-93-2 1230 PROPANEAMIDE, N-ETHYL- 101 5129-72-6 1520 36.6 PROPANEAMIDE, N-METHYL- 87 1187-58-2 239 36.6 PROPANEAMIDE, N-METHYL- (SSA16D) 87 1187-58-2 1231 PROPANEANIDE, N-(2-NETHYLPYRIDYL)- 164 257 PROPANEANIDE, N-(2-PICOLINYL)- (SW37D) 164 2027 5.9 17.4 PROPANENITRILE 55 107-12-0 945 PROPANENITRILE, 2-HYDROXY- (LACTONITRILE) 71 78-97-7 2064 37.4 PROPANENITRILE, 2-NYDROXY- (LACTONITRILE) 71 78-97-7 946 PROPANENITRILE, 2-HYDROXY-2-METHYL- 85 75-86-5 2015 23.1 PROPANENITRILE, 2-NETHYL- (ISOBUTYRONITRIIE) 69 78-82-0 2181 6.9 13.6 PROPANENITRILE, 2-OXO- 69 631-57-2 420 PROPANENITRILE, 3,31-THIOBIS- (SULFIDE,BIS-(2-CYANOETHYL)-) (SW23 1D) 140 111-97-7 294 PROPANENITRILE, 3-PHENYL- (SW1190) 131 269 PROPANENITRILE, 3-(2-PYRIDYL)- (SNW07D) 132 35549-47-4 717 PROPANE-1,2,3-TRIOL, 1-ACETATE-2-FORNATE- (SR175D) 162 61892-59-9 1497 71.5 PROPANE-1,2,3-TRIOL, 1-FURFURYL ESTER (GLYCEROL, 1-FURFURYL ESTER) {SNN121D 172 20390-21-0 728 50.3 PROPANE-1,2,3-TRIOL, mono-ACETATE (GLYCEROL, mono-ACETATE) 88 26446-35-5 235 53.4 PROPANE-1,2,3-TRIOL, TRIACETATE- (TRIACETIN) 218 102-76-1 228 62.2 56.2 PROPANE-1,2,3-TRIOL (GLYCEROL) 92 56-81-5 149 32.7 PROPANE-1,2-DIOL 76 57-55-6 723 PROPANE-1,2-DIOL, 1-ACETATE 118 . 627-69-0 724 PROPANE-1,2-DIOL, 2-ACETATE 118 6214-01-3 851 53.7 53.8 PROPANE-1,2-DIOL, 3-CHLORO- 110 96-24-2 1730 53.7 53.8 PROPANE-1,2-DIOL, 3-CHLORO- 110 96-24-2 852 PROPANE-1,2-DIOL, 3-0-FURFURYL- (SNN121D) 172 20390-21-0 1608 40.0 PROPANE-1,2-DIONE, 1-(2-FURYL)- (SR152C) 138 1438-92-2 1653 44.1 PROPANE-1,2-DIONE, 1-(S-NETHYL-2-Fl1RANYL)- 152 1197-20-2 1627 42.5 PROPANE-1,3-DIOL 76 S04-63-2 853 42.5 PROPANE-1,3-DIOL 76 504-63-2 1689 42.4 PROPANE-1,3-DIOL, 2,2-DINETNYL- 104 126-30-7 124 29.1 30.9 PROPANOIC ACID 74 79-09-4 740 PROPANOIC ACID, 1-HYDR01(Y-2-PROPYL ESTER (SNN110D) 132 S4541-18-3 738 PROPANOIC ACID, 2,3-EPODfY-4-NYDRO(YBUTYL ESTER 160 61892-62-4 731 PROPANOIC ACID, 2-HYDROXY, ETNYL ESTER (LACTIC ACID, ETHYL ESTER) 118 97-64-3 658 46.9 PROPANOIC ACID, 2-HYDROXY- (LACTIC ACID) 90 50-21-5 119 PROPANOIC ACID, 2-NETHYL- (ISOBUTYRIC ACID) 88 79-31-2 1740 15.0 PROPANOIC ACID, 2-OXO-, METHYL ESTER (PYRUVIC ACID, METNYL ESTER) 102 600-22-6 665 PROPANOIC ACID, 2-OXO- (PYRUVIC ACID) 88 127-17-3 110 PROPANOIC ACID, 2-PHENYL- 150 492-37-5 663 PROPANOIC ACID, 3-HYDROXY- 90 503-66-2 39

TOBACCO.WK1 Retention Time Databese - September S, 1989 Sorted by Campoisd Name RT (min) CNPD # DBWAX DB1 COMPOUND NAME NY CAS Nt!lIBER .... ----- ----- -------------------------------------------------------------------- --- ---- ------------- 2118 50.2 PROPANOIC ACID, 3-HYDROXY-2-METNYL-, METHYL ESTER 118 80657-57-4 2133 32.3 PROPANOIC ACID, 3-NYDRONY-2-METHYL-., METHYL ESTER- 118 111 PROPANOIC ACID, 3-PNENYL- 150 501-52-0 1515 91.8 PROPANOIC ACID, 3-(4-HYDROXYPNENYL)-, METHYL ESTER 180 5597-50-2 2004 6.8 17.6 PROPANOL-1 60 71-23-8 1790 44.9 PROPANOL-1, 1-PNENYL- 136 93-54-9 1602 60.6 PROPANOL-1, 1-(4-METHOXYPHENYL)- 166 5349-60-0 854 PROPANOL-1, 2,3-ONIDO- (GLYCIDOL) 74 556-52-5 1938 24.6 PROPANOL-1, 2-METHYL- 74 78-83-1 1783 51.9 PROPANOL-1, 3-PHENYL- 136 122-97-4 2143 91.5 PROPANOL-1, 3-(4-HYDROXYPHENYI)- 152 10210-17-0 2007 3.8 12.5 PROPANOL-2 60 67-63-0 1975 3.8 12.5 PROPANOL-2 60 67-63-0 2062 3.8 12.5 PROPANOL-2 60 67-63-0 2034 3.8 12.5 PROPANOL-2 158 67-63-0 830 PROPANONE-1, 1(1N-PYRROL-2-YL)- (PYRROLE, 2-PROPIONYL-) 123 1073-26-3 176 38.2 73.2 PROPANONE-1, 1-PHENYL- (PROPIOPHENONE) 134 93-55-0 462 PROPANONE-1, 1-(2-FURANYL)- (FURAN, 2-PROPIONYL-) 124 3194-15-8 476 45.8 PROPANONE-1, 1-(3-PYRIDINYL)- (588155D) 13S 1S70-48-5 1613 44.1 PROPAMONE-1, 1-(4-PYRIDINYL)- 135 1701-69-5 477 PROPANONE-1, 1-(4-PYRIDINYL)- (PYRIDINE,4-PROPIONYL-) (SBB252D) 13S 1701-69-5 2125 26.3 46.6 PROPANONE-2, 1-ACETYLOXY- 116 192 17.1 26.4 PROPANONE-2, 1-HYDROXY- (ACETOL) 74 116-09-6 1576 28.2 PROPANONE-2, 1-(2-FURANYL)- 124 6975-60-6 815 PROPANONE-2, 1-(5-HYDROXYMETNYl-2-FURANYL)- 154 50672-03-2 727 26.3 48.9 PROPANONE-2, 1-(ACETYLOXY)- 116 592-20-1 1748 38.0 PROPANONE-2, 1-[TETRANYDRO-3-(1-METNYLETHYL)-2-FURANYL] 170 38713-24-5 822 PROPANONE-2, 4-HYDROHYPHENYL- (SR237D) 150 770-39-8 821 PROPANONE-2, 4-HYDROD(Y-3-METNOD(YPHENYL- (SR144D) 180 2503-46-0 1584 55.7 PROPANONE-2, 4-METHOXYPHENYL- 164 122-84-9 472 PROPANONE-2, AMINO- 73 298-08-8 1958 2.4 11.4 PROPANONE-2 (ACETONE) 58 67-64-1 1973 2.4 11.4 PROPANONE-2 (ACETONE) 58 67-64-1 431 PROPENANIDE, 3-PNENYL- (CiNNAM1DE, SW217D) 147 621-79-4 1244 PROPENE-1, 3-METHYLTHIO- (NETHYL ALLYL SULFIDE) 88 7394-44-7 1245 PROPENE-1, 3-PROPYLTHIO- (PROPYL ALLYL SULFIDE) 116 27817-67-0 1246 PROPENE-1 3- HIOL 74 2028-39-9 , T 644 PROPENIC ACID-2 (ACRYLIC ACID) 72 79-10-7 98 83.3 PROPENOIC ACID, 3-PNENYL-(E) (CINNAMIC ACID) 148 140-10-3 1304 PROPEN-2-AMINO-1 57 107-11-9 835 9.9 16.8 PROPEN-2-OL-1 (ALLYL ALCOHOL) 58 107-18-6 1744 10.7 16.3 PROPEN-2-OL-1 (ALLYL ALCOHOL) 58 107-18-6 2001 9.9 16.8 PROPEN-2-OL-1 (ALLYL ALCOHOL) S8 107-18-6 278 48.1 PROP-2-ENAL, 2-NETNYL-3-(5-METHYL-2-FURYL)- (SYW950) 150 31704-79-7 167 50.9 PROP-2-ENAL, 3-PHENYL- (CINNANIC ALDENYDE) 132 104-SS-2 1872 65.5 PROP-2-ENAL, 3-PHENYL-21-METNOXY- (CINNANALDEHYDE, 21-NIETHOXII-) 162 1504-74-1 1793 60.7 PROP-2-EN-1-OL, 3-PHENYL- (CINNANYL ALCOHOL) 134 104-54-1 1255 PURINE, 6-AM1N0- (ADENINE) 135 73-24-5 1346 PUR1NE-2,6-DIONE-1H, 3,7-DINYDRO-1,7-DIMETNYL- 180 58-SS-9 942 PURINE-2,6-D10NE-(1N), 3,7-DINYDRO-3,7-DIMETHYL- (THEOBROMINE; 3,7-DIMETHYLX 180 83-67-0 1190 Pl1RINE-9H 120 51953-03-8 61 38.2 PYRAN, 2-ACETONYL-3-(1-NETHYLETHYL)-6-NETHYL-TETRAHYDRO- (SR48C) 198 39815-68-4 59 32.8 PYRAN, 2-(2-OXOPROPYL)-4-NETHYL-TETRAHYDRO- (SR46C) 156 20194-70-1 856 PYRAN, 3-NYDROXYTETRAHYDRO- 102 19752-84-2 1776 20.3 PYRAN, 4-N£THYL-2-(2-METHYL-1-PROPENYL)-TETRANYDRO- (ROSE OXIDE) 154 16409-43-1 711 PYRANONE-2(2N), 3,4,5,6-TETRANYDRO- 100 S42-28-9 709 PYRANONE-2(2N), 3,4,5,6-TETRAHYDRO-S-HYDROXY- (SR400) 116 33691-73-5 1751 38.6 PYRANONE-2(2H), 3,4-DiNYDR0-4-(1-NETNYLETHYL)-6-METHYI- iS4 1674 40.8 PYRANONE-2(2H), 4,6-DINETHYL-TETRAHYDRO- (SR89C) 128 3720-20-5 72 41.3 PYRANONE-2(2H), 4-NETNYL-TETRAHYDRO- (SR88C) 114 1121-84-2 1672 51.3 PYRANONE-2(2H), 4-(1-NETHYLETHYU-TETRANYDRO- (BT-15) 142 37147-17-4 1758 50.9 PYRANONE-2(2H), 4-(1-NETNYLETNYL)-TETRAHYDRO- (S015C) 142 21754-22-3 74 50.9 PYRANONE-2(2H), 4-(1-METHYLETHYL)-TETRAHYDRO- (S01SC) 1i2 21754-22-3 1676 55.6 PYRANONE-2(2H), S,6-DINYDRO-4-(1-METHYLETNYL)- (SR90C) 140 21722-33-8 1670 42.7 PYRANONE-2(2H) 5 6-DIMETHYL-TETRANYDRO- 128 10413-18-0 1753 48.7 , , PYRANONE-2(2H), 6,6-DINETHYL-4-(1-METHYLETHYL)-TETRANYDRO- 170 59056-32-5 1754 51.3 PYRANONE-2(2H), 6-METHYL-5-(1-METHYLETNYL)-TETRANYDRO- 156_60393-63-7 62 PYRANONE-2(2H), TETRAHYDRO-6-METNYL-3-(1-NETHYLETNYL)- (SR50C) 156 21722-34-9 1675 45.2 PYRANONE-2(2H), TETRAHYDRO-6-NETHYL-3-(1-METHYLETHYL)- (SR50C) . 1S6 21722-34-9 1671 50.0 PYRANONE-2(2H), TETRAHYDRO-6-METNYL-4-(1-NETHYLETNYL)- 1S6 823 PYRANONE-4(4N), 2,3-DIHYDR0-3,5-DINYDROXY-6-NETNYL- 144 28564-83-2 40

TOBACCO.WK1 Retention Time Databsse - Septeaber 5, 1989 Sorted by Cc.poutd Na.e RT (oin) CMPD ----------- * DBYAX DB1 COIIPOINiD NAME MW CAS NIMBER -------------------------------------------------------------------- --- ---- ------------- 828 PYRANONE-4(4H), 2-HYDRONY-3-NETHYL- (SR147D) 126 61892-88-4 76 PYRANONE-4(4H), 3,5-DIHYDROD(Y- 128 488-18-6 825 PYRANONE-4(4H), 3,5-DIHYDRONY-2,6-DINETHYL- 1S6 61892-86-2 824 PYRANONE-4(4H), 3,5-DINYDRONY-2-NETHYL- (SNN8D) 142 1073-96-7 827 PYRANONE-4(4H), 3-HYDRONY- (SNN1D) 112 496-63-9 135 48.8 PYRANONE-4(4H), 3-NYDROD(Y-2-METHYL- (MALTOL) 126 118-71-8 826 PYRANONE-4(4H), 3-HYOROXY-S-NETHYL- (SR138D) 126 42508-10-1 829 PYRANONE-4(4H), 5-NYDRONY-2-NETHYL- 126 644-46-2 2124 23.5 48.6 PYRANONE-4(4H), TETRAHYDRO- 100 29943-42-8 380 PYRAN-2H-2-CARBONALDEHYDE, 3,4-DIHYDRO- 112 100-73-2 1636 38.6 PYRAN-(4H), 5,6-DIHYDRO-2,6-DINETNYL-3-CARB00(LATE, METNYL ESTER 184 85373-77-9 855 PYRAN-(4N), 5,6-DiNYDRO-S-NYDROXY-2-HYDRONYNETHYL- 130 61892-96-4 1106 13.2 35.0 PYRAZINE 80 290-37-9 1110 PYRA2INE, 2,3-DIETHYL-5-METHYL- 1S0 18138-04-0 1495 19.7 53.2 PYRA2INE, 2,3-DIMETHYL- 108 5910-89-4 593 19.7 53.4 PYRAZINE, 2,3-DIMETNYL- 108 5910-89-4 594 25.6 PYRAZINE, 2,3-DIMETHYL-S-ETHYL- 136 15707-34-3 1111 PYRAZINE, 2,5-DIETHYL-3-METHYL- 150 32736-91-7 100 18.5 52.4 PYRAZiNE, 2,5-DINETHYL- 108 123-32-0 1492 18.5 52.4 PYRAZINE, 2,5-DIHETHYL- 108 123-32-0 1359 18.5 52.4 PYRAZINE, 2,5-DINETHYL- 108 123-32-0 1362 18.5 52.4 PYRAZINE, 2,5-DINETNYL- 108 123-32-0 1112 PYRA2INE, 2,5-DINETHYL-3-ETHENYL-, (wrong in TOBACCO.L) 134 8093S-98-4 595 PYRAZINE, 2,5-DINETHYL-3-ETHYL- 136 13360-65-1 1109 PYRAZINE, 2,6-DIETNYL-3-METHYL- 150 18138-05-1 102 18.9 PYRAZINE, 2,6-DINETHYL- 108 108-50-9 1358 18.9 PYRAZiNE, 2,6-DINETHYL- 108 108-50-9 1494 18.9 52.4 PYRAZINE, 2,6-DINETNYL- 108 108-50-9 1113 PYRAZiNE, 2,6-DiNETNYL-3-ETHENYL- 134 1108 PYRAZiNE, 2-BUTYL- 136 29460-91-1 603 PYRAZINE, 2-ETHENYL-5-METHYL- 120 13925-08-1 604 PYRA2INE, 2-ETHENYL-6-NETHYL- 120 13925-09-2 599 22.6 PYRA2INE, 2-ETHYL-3-NETHYL- 122 15707-23-0 1496 22.6 PYRAZINE, 2-ETHYL-3-METHYL- 122 15707-23-0 598 22.2 PYRAZINE, 2-ETHYL-5-NETHYL- 122 13360-66-0 600 PYRAZINE, 2-ETHYL-6-METHYL- 122 13925-03-6 1467 PYRAZINE, 2-FORNYL-5-(2-FURYL)-3-METHYL- 188 NO 8 GIVEN 601 PYRA2INE, 2-FURANYL- 146 32736-95-1 844 PYRAZINE, 2-HYDROXETHYL- (SR192D) 192 6705-31-3 1425 PYRAZINE, 2-HYDROXYMETHYL-3-METHYL- 124 1706 46.3 PYRA2INE, 2-HYDROXYMETHYL-3-METHYL- 124 1360 PYRAZINE, 2-NYDROD(Y-, [PYRA2INONE-2(1N)] 96 6270-63-9 1364 PYRAZINE, 2-HYDROXY-3-METNYL- 110 19838-07-4 1361 PYRA2INE, 2-HYDROXY-3-METHYL- 110 19838-07-4 936 PYRAZINE, 2-NYDROXY-3-METHYL- (SR2000) 110 19838-07-4 1365 21.3 PYRAZINE, 2-METH00(Y-3-METHYL- 124 2847-30-5 1368 28.7 PYRAZINE, 2-METNOXY-3-(2-METHYLPROPYL)- 166 24683-00-9 1369 PYRAZINE, 2-METHYL-3-PHENYL- 170 29444-53-9 937 PYRAZINE, 2-METHYL-3-PHENYL- 170 294ti4-53-9 1122 61.5 PYRA2INE, 2-HETHYL-5-PHENYL- 170 58861-90-8 602 PYRA2INE, 2-METHYL-5-PROPYL- 136 29461-03-8 1120 PYRA2INE, 2-METHYL-5-(1-HETHYLETHYL)- 136 13925-05-8 1121 62.2 PYRAZINE, 2-METHYL-6-PHENYL- 170 74233-03-7 1126 PYRAZINE, 2-METHYL-6-PROPYL- 136 294"-46-0 1124 PYRAZiNE, 2-PENTYL- 150 6303-75-9 433 PYRAZINE, 2-PHENYLNETNYL- (SiW207D) 170 28217-95-0' 1123 PYRA2INE, 2-PHENYL- 156 29460-97-7 1366 PYRA2INE, 2-PHENYL- 156 29460-97-7 605 PYRA2INE, 2-PROPYL- 122 18138-03-9 1118 PYRAZINE, 2-(1-METHYLETHENYL)- 120 38713-41-6 1165 PYRAZINE, 2-(1-METHYLETHYL)- 122 29460-90-.0 1107 PYRAZINE, 2-(2-BUTENYL)- 134 29460-93-3 1604 51.0 PYRAZINE, 2-(2-FURANYL)-3-HETNYL- 160 32737-01-2 1114 PYRA2INE, 2-(2-FLitANYL)-3-NETHYL- 160 32737-01-2 1115 PYRAZINE, 2-(2-FURANYL)-5-METHYL- (SR197D) 160 27610-38-4 1117 PYRAZINE, 2-(2-FURANYL)-5-METHYL- (SR209C,ISOMER *1115) 160 1116 PYRAZINE, 2-(2-FURANYL)-6-METHYL- (SR210C) 160 32737-03-4 596 25.2 PYRAZINE, 3,5-DINETHYL-2-ETHYL- (SBB249D) 136 13925-07-0 - 1119 PYRAZINE, 3-NETHYL-2-(1-METHYLETHYL)- -81-9 , 136 15986 1493 33.2 PYRA2INE, ACETYL-, (ETHANOME, 1-PYRAZINYL-) 122 22047-25-2 607 PYRAZINE, ETHENYL- 106 4177-16-6 '. 41

TOBACCO.WK1 Retention Time Database - Septeaber S, 1989 Sorted by Coapasw Name RT (min) , CMPD ----------- # DBWAX DB1 OOMPOUND NAME NW Clls NtNUR ---- ----- ----- -------------------------------------------------------------------- --- -- 597 19.1 52.9 PYRAZINE, ETHYL- 108 13925-00-3 1491 15.7 PYRAZINE, METHYL- 94 109-08-0 223 15.7 PYRAZINE, METHYL- 120 109-08-0 606 26.3 PYRAZINE, TETRAMETHYL- 136 1124-11-4 152 22.5 60.2 PYRAZINE, TRIMETHYL- 122 14667-SS-1 134 22.5 60.2 PYRA2INE, TRIMETHYL- 122 14667-55-1 845 PYRA2INEETHANOL, 3-METHYL- (SR194D) 138 61892-92-0 1650 55.0 PYRA2INEETHANOL, 3-METHYL- (SR1940) 138 61892-92-0 1426 56.1 PYRAZINEETHANOL, 6-METHYL- 138 61892-93-1 846 PYRAZINEETHANOL, 6-NETNYL- 138 61892-93-1 251 PYRAZINEMETHANOL, S-METHYL- 124 61892-95-3 1664 53.1 PYRAZINEMETHANOL, 5-METHYL- 124 61892-95-3 1383 97.9 PYRA2INE-1,4-D10NE, 3-(1-IETNYLETHYL)-PYRROLO[1,2a7- (SL34D) 196 331 PYRAZiNONE-2(1N), 3-(1-IETNYLETHYL)-1-METHYL- (SWW167D) 152 78210-68-1 1363 PYRAZINONE-2(1H) (PYRA2INE, 2-NYDRONY-) 108 6270-63-9 1166 42.8 PYRAZOLE-1H 68 288-13-1 1168 PYRAZOLE-1H, 1-NETHYL- 82 930-36-9 1167 PYRAZOLE-1H, 3,4,5-TRIMETHYL- 110 5519-42-6 203 48.0 PYRAZOLE-1H, 3,4-DIMETHYL- 96 2820-37-3 104 44.6 58.2 PYRAZOLE-1H, 3,5-DINETHYL- 96 67-S1-6 177 51.3 PYRAZOLE-1H, 3-NETNYL- 82 1453-58-3 1564 42.9 51.3 PYRAZOLE-1H, 3-METNYL- 82 1453-58-3 202 PYRAZOLE-iN, 4-BROMO-3-METHYL- 160 13808-64-5 1912 44.9 53.5 PYRA20LE-1N, 4-METHYL- 82 7554-65-6 1347 PYRAZONE-2, 1-METNYL-3-PROPYL- 152 1762 37.5 PYRIDAZINE 80 289-80-5 486 46.2 PYRIDINMINE-2 94 S04-29-0 1310 47.0 PYRIDINAMINE-2, 6-METHYL- 108 1824-81-3 1307 PYRIDINAMINE-2, N-2-PYRIDINYL- 171 1202-34-2 1308 57.5 PYRIDINANINE-3 94 462-08-8 1309 54.8 PYRIDINAMINE-3, N-NETHYL-6-METHOXY- 138 61771-67-3 487 PYRIDINAMINE-4 94 504-24-5 219 11.9 36.4 PYRIDINE 79 110-86-1 997 PYRIDINE, 2,3,5-TRIMETHYL- 121 695-98-7 133 21.3 60.8 PYRIDINE, 2,3,6-TRIMETHYL- 121 1462-84-6 510 19.9 55.5 PYRIDINE, 2,3-DINETHYL- 107 S83-61-9 1581 32.9 PYRIDINE, 2,3-TRINETHYLENE- 119 996 20.8 59.3 PYRIDINE, 2,4,6-TRIMETHYL- 121 108-75-8 115 18.8 54.2 PYRIDINE, 2,4-Dl1ETHYL- 107 108-47-4 1577 63.6 PYRIDINE, 2,4-DINETHYL-1-OXIDE- 123 1122-45-8 511 18.4 54.3 PYRIDINE, 2,5-DIMETHYL- 107 589-93-S 99 18.3 54.3 PYRIDINE, 2,5-DINETNYL- 107 589-93-5 116 15.0 50.1 PYRIDINE, 2,6-DINETHYL- 107 108-48-5 983 PYRIDINE, 2,6-DINETHYL-3-ETHYL- 135 23580-52-1 984 PYRIDINE, 2,6-DINETHYL-4-ETHYL- 135 36917-36-9 301 148.3 PYRIDINE, 2,6-DIPHENYL- (SW112D) 231 3558-69-8 88 32.1 PYRIDINE, 2-ACETYL- (ETHANONE, 1-(PYRIDINYL-) 121 1122-62-9 401 38.2 PYRIDINE, 2-ACETYL-4,6-DINETHYL- (SW249D) 149 59576-31-7 309 PYRIDINE, 2-ACETYL-4-METHYL- (SW155D) 135 S9S76-26-0 517 PYRIDINE, 2-BUTYL- (SBB237D) 135 S058-19-5 548 PYRIDINE, 2-ETHENYL- (S6B228D) 105 100-69-6 538 PYRIDINE, 2-ETHENYL-3-METHYL- (SB62350) 119 22382-94-1. 1024 PYRIDINE, 2-ETHOXY- 123 14529-53-4 520 16.4 PYRIDINE, 2-ETHYL- 107 100-71-0 1599 16.4 PYRIDINE, 2-ETHYL- 107 100-71-0 995 PYRIDINE, 2-ETHYL-3-METHYL- 121 56986-88-0 522 PYRIDINE, 2-ETHYL-4-METHYL- 121 2150-18-7 985 22.0 PYRIDINE, 2-ETHYL-S-METHYL- (SBB108D) 121 18113-81-0 523 PYRIDINE, 2-ETHYL-6-METHYL- 121 1122-69-6 437 PYRIDINE, 2-ETHYL-6-PHENYL- (SYW212D) 183 S9239-12-2 1002 PYRIDIME, 2-METHOXY- 109 1628-89-3 1003 13.3 43.7 PYRIDINE, 2-NETHYL- (PICOLINE-2) 93 109-06-8 532 PYRIDINE, 2-METHYL-4-PHENYL- (SBB259D) 169 1.5032-21-0 1007 PYRIDINE, 2-METNYL-5-(1-METHYLETHENYU- (SR263C) 133 56057-93-3 1655 25.8 2-METNYL-S-(1-NETHYLETHYL)- (SR95C) PYRIDINE 13S 20194-71-2 1006 , PYRIDINE, 2-METHYL-5-(1-NETHYLETHYL)- (SR95C) 135 20194-71-2 1587 54.6 PYRIDINE, 2-METHYL-5-(2-HYDROD(Y-2-PROPYL)- 151 1014 PYRIDINE, 2-PENTYL- 149 2294-76-0 292 PYRIDINE, 2-PHENYLMETNYL- (SITY127D) 169 101-82-6 540 58.7 93.2 PYRIDINE, 2-PHENYL- 155 1008-89-5 545 PYRIDINE, 2-PROPYL- 121 622-39-9 42

TOBACCO.WK1 Retention Time Database - Septesber 5, 1989 CMPD Sorted by Cc.hourd Nawe 8 DBWAX DB1 COMPOUND NAME ---- ----- ----- ------------------------- -- - .. 1698 52.3 PYRIDINE, 528 PYRIDINE, 291 PYRIDINE, 543 PYRIDINE, 186 33.9 PYRIDINE, 535 PYRIDINE, 1700 52.0 PYRIDINE, 347 PYRIDINE, 424 PYRIDINE, 404 PYRIDINE, 406 25.4 PYRIDINE, 512 25.2 60.5 PYRIDINE, 103 25.2 PYRIDINE, 992 PYRIDINE, 105 22.4 58.3 PYRIDINE, 514 PYRIDINE, 991 PYRIDINE, 253 PYRIDINE, 38 42.6 67.7 PYRIDINE, 430 PYRIDINE, 403 PYRIDINE, 293 PYRIDINE, 395 PYRIDINE, 515 PYRIDINE, 518 PYRIDINE, 982 PYRIDINE, 171 26.3 PYRIDINE, 521 20.9 56.7 PYRIDINE, 224 20.9 56.7 PYRIDINE, 986 PYRIDINE, 524 PYRIDINE, 529 31.6 PYRIDINE, 530 PYRIDINE, 218 16.6 48.0 PYRIDINE, 2185 59.0 95.5 PYRIDINE, 1586 64.9 PYRIDINE, 295 PYRIDINE, 2184 59.1 93.2 PYRIDINE, 541 58.4 93.4 PYRIDINE, 546 PYRIDINE, 1017 PYRIDINE, 990 PYRIDINE, 1682 55.1 PYRIDINE, 999 PYRIDINE, 1722 56.1 PYRIDINE, 527 PYRIDINE, 1521 32.9 PYRIDINE, 1010 PYRIDINE, 1009 PYRIDINE, 1029 PYRIDINE, 1012 PYRIDINE, 544 30.4 PYRIDINE, 353 PYRIDINE, 436 PYRIDINE, 1011 PYRIDINE, 329 PYRIDINE, 296 PYRIDINE, 988 PYRIDINE, 987 PYRIDINE, 981 PYRIDINE, 421 PYRIDINE, 533 PYRIDINE, 434 PYRIDINE, 1004 PYRIDINE, 319 PYRIDINE, 290 PYRIDINE, 272 PYRIDINE, 1005 PYRIDINE, 1610 55.0 PYRIDINE, 302 PYRIDINE, 547 PYRIDINE, RT (min) 2-(1-NYDRONY-1-PENTYL)- (PROPOSED) 2-(1-METHYLETNYL)-3-METHYL- (566200D) 2-(1-METHYLPYRROL-2-YL) (NICOTYRINE-A, SW1260) 2-(1-PROPENYL)- (S662360) 2-(2-METHOXYETHYL)- 2-(2-METHYLPROPYL)- (SBB253D) 2- (5-MET HYL-2-Ft1RA11YLMETHYL )- 2-(C3-ALKYLPHENYL)- (S{iW203) 2-(C3-ALKYLPHENYL)- (SN1R220) 3,31-METHYLENEBIS (SWW2450) 3,41-METHYLENEBiS- (SWA42D) 3,4-DIMETHYL- 3,4-DIMETHYL- 3,4-DIPHENYL- 3,5-DIMETHYL- 3,5-DiMETHYL- 3,5-DIPHENYL- 3-ACETOXY- 3-ACETYL- 3-ACETYL-1,2-DiHYDR0-2-METNYL- (SITY216D) 3-ACETYL-5-METNYL- (SM1251D) 3-ACETYL-5-NETNYL- (SYY2510) 3-ACETYL-6-METHYL- (SfA2550) 3-ALLYL- (SBB2470) 3-BUTYL- (SB82390) 3-BUTYL-2,6-DINETHYL- (SW990) 3-ETHENYL- 3-ETHYL- 3-ETHYL- 3-ETHYL-4-METHYL- 3-ETHYL-5-METHYL- (SBB2500) 3-METHOXY- (SB8193D) 3-METHOXY-5-METHYL- (566206D) 3-METHYL- (PICOLINE-3) 3-METHYL-2-PHENYL- 3-METHYL-N-OXIDE- 3-PENTYL- (Si1Y122D) 3-PHENYL- 3-PHENYL- (586258D) 3-PROPYL- 3-(1,3,3-TRIMETHYL-2-PYRROLIDINYL)- 3-(1,5-DINETHYL-2H-PYRROL-2YU- (SWM1100) 3-(1H-PYRROL-1-YL)- (SBB192D) 3-(1-ETHYl-2-PYRROIIDINYL)- (ETHYL NICOTINE) 3-(1-NYDROXYETHYL)- 3-(1-METNYLETHENYL)- 3-(1-METHYIETNOxY)- 3-(1-METHYL-I-ODIIDE-2-PYRROLIDINYL)- 3-(1-METHYL-2-PYRROIiDINYL)-N,1-D10X1DE,(S)- 3-(1-METHYl-5-HYDROD(YPYRROLIDIN-2-YL)- (SL29) 3-(1-NITROSO-2-PIPERIDINYU- 3-(1-PROPENYL)- (SBB204,121D) 3-(2-BUTENYL)- (S1N200D) 3-(2-ETHYLPHENYL)- (SW2110) 3-(2-METHYL-IH-PYRROL-1-YL)- 3-(2-PHENYLETHYL)-. (S1N172D) 3-(2-TETRAHYDROFURYL)- (SW1150) 3-(3,4-HYDRO-2-METHYl-2N-PYRROL-5-YL)- 3-(3,4-HYDRO-3-METHYL-2N-PYRROL-5-YL)- (SWY176) 3-(3-BUTENYL)- (588202D,SNN91D) 3-(3-ET-3,4-HYDRO-2H-PYRROL-5-YL)- (SYW2250) 3-(3-METHYLPHENYU- (SB8146D) 3-(3-METHYLPHENYL)- (S11LR09D) 3-(3-PENTEN-2-YL)- (SW124D) 3-(4-ETHYLPHENYL)- (SIN128D) 3-(4-METHYLPENTYL)- (SSN1250) 3-(4-METNYL-3-PENTENYL)- (SW104D) 3-(5-METHYL-2-FURFURYL)- (SWi1102D) 3-(5-METHYL-2-FURFURYL)- (SYW102D) 3-(N,3-DIMETHYLPYRROL-2-YL)- (SW114D) 3-(PYRROL-I-YL)- (s681920) MN CAS NIRIBER 165 135 72693-04-0 158 487-19-4 119 17618-94-9 137 114-91-0 135 6304-24-1 173 197 197 170 78210-43-2 170 78210-44-3 107 S83-S8-4 107 583-58-4 231 107 591-22-0 107 591-22-0 231 92-07-9 137 17747-43-2 121 350-03-8 137 78210-69-2 135 42972-46-3 135 42972-46-3 T14170-3 135 36357-38-7 119 7300-28-9 135 539-32-2 163 6760-12-9 105 1121-S5-7 107 536-78-7 107 536-78-7 121 529-21-5 121 3999-78-8 109 7295-76-3 123 78210-42-1 92 108-99-6 169 10273-90-2 109 1003-73-2 149 1802-20-6 155 1008-88-4 155 1008-88-4 121 4673-31-8 190 36127-43-2 172 65734-44-3 144 72692-99-0 176 91429-66-2 123 4754-27-2 119 6515-13-5 137 88/11-63-1 178 491-26-9 194 205S-29-0 178 2S110-79-6 191 1133-64-8 119 15376-62-2 133 78210-90-9 183 158 78210-49-8 183 6312-09-0 149 78210-50-1 160 65719-03-1 160 78249-81-7 133 71532-24-6 174 78210-39-6 169 4385-67-5 169 90395-49-6 147 183 78210-41-0 163 72692-97-8 161 2057-39-8 173 78210-46-5 173 78210-46-5 172 78210-38-S 144 50966-74-0 43

) TOBACC0.1AC1 Retention Time Database - Septamber S, 1989 Sorted by Coapoud NaMI-9 RT (min) CMPD ----------- ! DBWAX DB1 COMPOUND NAME M{I CA8 NIMBER ---- ----- ----- ----------------------------------------------------------------------- ---- ------------- 967 PYRIDINE, 3-[1-METHYL-2-(1-METHYLETNYL)-1N-IMJIDAZOYL-5-YL]- (SEE /1000) ~ 201 78210-84-1 994 PYRIDINE, 3-[1-(5-ETHYL-2-F(NUNYL)-1H-PYRROL-2-YLI- 238 78210-88-5 1015 PYRIDINE, 3-[1-(5-PROPYL-2•FI1R/111YL)-1H-PYRROL-2-YL]- (SYY67D) 252 78210-89-6 519 PYRIDINE, 4-BUTYL- (S68157D) 135 5335-75-1 993 27.1 PYRIDINE, 4-ETHENYL- 105 100-43'6 2186 22.0 57.8 PYRIDINE, 4-ETHYL- 107 536-75-4 513 22.3 PYRIDINE, 4-ETHYL- 107 536-?S-4 1023 PYRIDINE, 4-METH01(YlNcTHYL- (SYM75D) 123 70199-60-9 114 16.9 48.8 PYRIDINE, 4-METHYL- (PICOLINE-4) 93 108-89-4 1008 PYRIDINE, 4-METHYL-2-PNENETNYL- (SW103D)(N0 MATCH) 197 7S83S-01-7 280 PYRIDINE, 4-METHYL-2-(3-METHYLBUTYL)- (SW97D) 163 78210-47-6 534 PYRIDINE, 4-METHYL-3-PNENYL- (5661450) 169 3475-21-6 542 60.1 93.7 PYRIDINE, 4-PHENYL- (5661760) 1SS 939-23-1 989 PYRIDINE, 4-(1,1-DIMETHYLETRYL)- 135 3978-81-2 516 PYRIDINE, 4-(1-BUTENYL)- (566150D) 133 78210-91-0 998 PYRIDINE, 4-(1-METHYLETNYL)- 121 696-30-0 474 PYRIDINE, 4-(2-OD(OPROYL)- 135 6304-16-1 435 PYRIDINE, 4-(2-PNENYLPROPYL)- (SW2100) 197 1018 PYRIDINE, 4-(4-HYDROHYBUTYL)- (SiA67D) 151 S264-1S-3 298 44.2 PYRIDINE, 5-ACETYL-2-METHYL- (SNW255D) 135 363S7-38-7 537 28.2 PYRIDINE, 5-ETHENYL-2-METNYL- 119 140-76-1 525 PYRIDINE, 5-ETHYL-2-METHYL- (588246D) 121 104-90-5 1019 PYRIDINE, 5-HYDROD(Y-2-HYDROHYMETNYL- 125 40222-77-3 531 PYRIDINE, 5-METHOXY-2-METHYL- 123 SS270-47-8 539 PYRIDINE, 5-METHYL-2-VINYL- (S6B251D) 119 3883-39-4 1020 PYRIDINE, 6-METHYL-3-(1-ME-2-PYRROLIN-2-YL)- (SR241C) 174 351 PYRIDINE, B1S-3,31-(1,2-ETHENEDIYL)- .(SW198D) 182 24950-44-5 526 PYRIDINE, C3-ALKYL- 121 335 PYRIDINE, SUBSTITUTED (SWY103D) 197 439 PYRIDINE, ?-(C3-ALKYLPHENYL)- 197 438 PYRIDINE, ?-(C3-ALKYLPHENYU- (SWW2130) 197 1001 PYRIDINE,3-[1-(5-METHYL-2-FllRAIIYLMETHYL)-3-PYRROLIN-2-YL]- (SWW86) 240 78210-45-4 388 PYRIDINEACETONITRILE-4 (588203D) 118 13121-99-8 412 PYRIDINEACRYLONITRILE-3, tis- (SWW235D) 130 54356-27-3 413 PYRIDINEACRYLONITRILE-3, trans- (SW236D) 130 54356-28-4 397 PYRIDINECARBONITRILE-2, 3-METHYL- (SWY2S7D) 118 20970-75-6 396 PYRIDINECARBONITRILE-2, 4-METNYL- (SN1~12S60)' 118 1620-76-4 386 PYRIDINECARBONITRILE-2 (568213D) 104 100-70-9 387 38.2 58.8 PYRIDINECARBONITRILE-3 104 100-54-9 275 PYRIDINECARBONITRILE-3, 4-METHYL- (SWW100D) 118 5444-01-9 276 PYRIDINECARBONITRILE-3, 5-METHYL- (SYN101D) 118 42885-14-3 2092 35.3 56.1 PYRIDINECARBOWITRILE-4 104 100-48-1 338 PYRIDINECARBONITRILE-5, 2-ETNYL- (SYW3D) 132 3222-52-4 2016 29.8 55.8 PYRIDINECARBOXALDEHYDE-2 107 1121-60-4 173 36.9 59.4 PYRIDINECARBOXALDEHYDE-3 (NICOTINALDEHYDE) 107 S00-22-1 410 PYRIDINECARBOXAMIDE-2, 4,6-DIMETHYL- (PICOL[NAMIDE-2, 4,6-DIMETHYL-) (SW24 150 72693-02-8 330 PYRIDINECARBOXAMIDE-2, 4-ETHYL- (PICOLINAMIDE-2, 4-ETHYL-) (Sw1173D) 150 32743-35-4 327 PYRIDINECARBOXAMIDE-2, S-ETHYL- (PICOLINAMIDE-2, S-ETHYL-) (SW178D) 1S0 13S09-17-6 357 PYRIDINECARBOXAMIDE-2, 5-METHYL- (PICOLINANIDE-2, S-METNYL-) (S11W19SD) 136 20970-77-8 316 PYRIDINECARBOXAMIDE-2, 6-ETHYL- (P1COLINAMIDE-2, 6-ETHYL-) (SWW131D) 150 78210-61-4 1349 PYRIDINECARBOXAMIDE-2, 6-METHYL- (PIODLINAMIDE-2, 6-METHYL-) 136 63668-37-1 180 64.8 PYR[DiNECARBO%AMIDE-2 (PICOLINAMIDE-2) (SW240D) 122 ,1452-77-3 1022 PYRIDINEETHANOL-2 123 103-74-2 1311 PYRIDIME-3-BUTANAMINE, N-METNYL- 164 3000-74-6 841 PYRIDINE-4-BUTANOL (BUTYL ALCOHOL, 4-(4-PYRIDINYL)-) 151 5264-15-3 1626 67.5 PYRIDINOL-2 . 95 142-08-5 883 66.4 PYRIDINOL-2 V5 142-08-S 1021 PYRIDINOL-2, 3,4-DIMETHYL- 123 95907-02-1 879 PYRIDINOL-2, 3,5-DIMETNYL- (SR206D) 123 3718-67-0 1517 67.5 PYRIDINOL-2, 3,6-DINETHYL- 123 5342&02-7 249 PYRIDINOL-2, 3,6-DIMETNYL- (SS1i128D) 123 S3428'02-7 1027 PYRIDINOL-2, 3-ETHYL- 123 882 PYRIDINOL-2, 3-METHYL- (SR201D) 109 91914-04-4 255 PYRIDINOL-2, 4,6-DIMETHYL- (SW36D) 123 16115-08-5 884 PYRIDINOL-2, 4-METHYL- 109 91914-0S-5 1025 PYRIDINOL-2, 5-ETHYL- 123 1026 PYRIDINOL-2, 5-ETHYL- (SPECTRA DIFF FROM 01025) 123 245 PYRIDINOL-2, 5-ETHYL- (SW19D) 123 62003-48-9 254 67.0 PYRIDINOL-2, 5-METHYL- (SWW3SD) 109 91914-06-6 881 PYRIDINOL-2, 6-ETHYL- (SR2050) 123 61892-99-7 247 PYRIDINOL-2, 6-METHYL- (S{W26D) 109 327'9-76-3 44

TOBACCO.WK1 Retention Tim Database - Septeaber 5, 1989 Sorted by Caspand Name RT (min) CMPD ----------- # DBWAX DB1 COMPOUND NAME MW CAS NIMBER ---- ----- ----- ------------------------------------------------•-------------------... .... ............. 885 65.9 PYRIDINOL-3 95 109-00-2 260 PYRIDINOL-3, 2,4-DINETHYL- (SW440) 123 27296-76-0 891 PYRIDINOL-3, 2,6-DINETHYL- (SL14D) 123 1122-43-6 889 PYRIDINOL-3, 2-ETHYL- (SNN109D) 109 61893-02-5 886 PYRIDINOL-3, 2-METHYL- (SR58D) 109 1121-25-1 894 PYRIDINOL-3, 2-PROPYL- 137 14159-68-3 890 PYRIDINOL-3, 4,6-DINETHYL- (SR59D) 123 27296-77-1 267 PYRIDINOL-3, 4-METHYL- (SIN290) 109 1121-19-3 1611 69.0 PYRIDINOL-3, 5-METNYL- 109 42732-49-0 888 68.9 PYRIDINOL-3, 5-METHYL- (SNN1110) 109 42732-49-0 1028 PYRIDINOL-3, 6-ETHYL- 123 S1834-96-9 259 PYRIDINOL-3, 6-ETHYL-2-METNYL- (SW42D) 137 42451-07-0 892 PYRIDINOL-3, 6-ETHYL-4-NET8YL- (SR1760) 137 61893-01-4 893 PYRIDINOL-3, 6-HYDROXYNETHYL- 125 40222-77-3 887 69.7 PYRIDiNOL-3, 6-METHYL- 109 1121-78-4 262 PYRIDINOL-3, (?)-C3 (SW45D) 137 261 PYRIDINOL-3, (?)-C3 (S{AW46D) 137 264 PYRIDINOL-3, (?)-C3 (SNW52D) 137 121 85.8 PYRIDINOL-4 95 626-64-2 248 53.0 73.2 PYRIDONE-2(iN), 1-METNYL- (S{AW250) 109 694-85-9 1915 53.0 PYRIDONE-2(1N), 1-METHYL- (SYH250) 109 694-85-9 585 PYRIDO[2,3b]-IND0LE-9H, 2-ACYL- (SY111650) 234 583 PYRIDO[2,3b]-INDOLE-9H, 2-BUTYL- (SW144D) 224 72693-00-6 581 PYRIDO[2,3b]-INDOLE-9H, 2-METNYL- (SW138D) 182 17276-85-6 584 PYRIDO[2,3b]-INDOLE-9H, 2-PENTYL- (SY11142D) 238 78210-53-4 582 PYR1D0[2,3b]-INDOLE-9N, 2-(2-METHYLPROPYL)- (SW152D) 224 78210-54-5 285 PYRIDO[3,4b]INDOLE-(9H), ETHYL- (SN62D) 196 20127-61-1 586 PYRIDO[3,4b]-INDOLE-9N, 1-PROPENYL- (SYY1430) 208 78210-55-6 579 PYRIDO[3,4b]-INDOLE-9N (NORRARMANE) (SBB264D) 168 244-63-3 580 PYRIDO[4,3-b]-(5H)INDOLE (CARBOLINE, panaie-) (SBB1860) 168 8001-81-8 1173 16.1 PYRIMIDINE 80 289-95-2 1171 PYRIMIDINE, 2,4-DIMETHYL- 108 14331-54-5 1170 PYRIMIDINE, 2,5-DINETHYL- 108 22868-76-4 1172 PYRIMIDINE, 4,5-DINETHYL- 108 694-81-5 1169 21.1 53.3 PYRIMIDINE, 4,6-DINETHYL- 108 1558-17-4 1916 18.6 PYRIMIDINE, 4-METHYL- 94 3438-46-8 943 PYRIMIDINE-2,4-DIONE(1N,3N), 3,5-DIMETNYL- (URACIL,3,5-DIMETHYL-) (SR163D) 140 4160-77-4 1633 PYRIMIDINE-2,4-DIONE(1N,3N), 3-METNYL- (URACIL, 3-METHYL-) 126 608-34-4 944 PYRIMIDINE-2,4-DIONE(1N,3H), 5,6-DIHYDRO-3-ETBYL-S-METHYL- (URACIL,5,6-DIHYD 1S6 61893-13-8 1384 PYRIMIDINE-2,4-DIONE(iN,3H) (l1RACIL) 112 66-22-8 1427 PYRIMIDINOL-4, 2,5-DINETHYL- 124 67383-34-0 1174 PYRIMIDINOL-4, 2,5-DINETHYL- 124 3059-71-0 938 PYRIMIDINOL-4, 2,5-DIMETHYL- (SR193D) 124 3059-71-0 1918 77.0 PYRIMIDINOL-4, 2,6-DINETHYL- 124 6622-92-0 315 PYRIMIDINONE-4, 2,3-METHYL-6-PHENYL-3,4,5,6-TETRAHYDRO- 200 779 PYROCOLL 186 484-23-1 1862 39.5 PYRONE, a[pha- 96 504-31-4 2188 33.1 60.5 PYRROLECARBOXALDEHYDE-2, 1-METHYL- 109 1192-58-1 1738 27.6 37.8 PYRROLE-1N 67 109-97-7 574 27.6 37.8 PYRROLE-1N 67 109-97-7 1083 PYRROLE-1H, 1-BEN2YL-2-METNYL- 171 78075-83-9 1084 PYRROLE-1N, 1-BUTYL- 123 S89-33-3 1091 PYRROLE-1N, 1-BUTYL-2-METHYL- 137 S0691-30-0 1089 PYRROLE-1N, 1-ETHYL- 95 617-92-5 1095 PYRROLE-IH, 1-ETHYL-2-METHYL- 109 19983-83-6 576 9.9 36.2 PYRROLE-IH, 1-METHYL- 81 96-54-8 1101 PYRROLE-1N, 1-PENTYL- 137 1551-12-8 1100 PYRROLE-1N, 1-PHENYL- 143 635-90-5 1098 PYRROLE-IH, 1-PROPYL- 109 5145-64-2 1085 PYRROLE-IH, 1-(1-CYCLOHEXENYL)- 147 62672-96-2 2022 74.1 PYRROLE-IH, 1-(2-FURANYLMETNYL)- 147 1438-94-4 1090 PYRROLE-IH, 1-(2-FURANYLMETNYL)- 147 1438-94-4 1102 PYRROLE-1H, 1-(2-METHYLPROPYL)- 123 20884-13-3 1094 PYRROLE-IH, 1-(2-METHYL-I-CYCLOHE)tEN-I-YL)- (SR64D) 161 66309-87-3 1093 PYRROLE-1N, 1-(3-METHYLBUTYL)- 137 13679-79-3 1092 PYRROLE-1H, 1-(5-METHYL-2-FURANYLIETNYL)- 161 13678-52-9 1087 PYRROLE-1H, 2,3-DIMETHYL- ~ 95 600-28-2 1086 PYRROLE-1H, 2,4-DINETHYL- 95 625-82-1 1096 32.0 52.6 PYRROLE-1H, 2,5-OIMETHYL- 95 625-84-3 478 48.2 PYRROLE-1H, 2-ACETYL- (SR72C) 109 1072-83-9 1817 35.0 PYRROLE-1H, 2-ACETYL-1-METHYL- 123 932-16-1 45

TOBACCO.WK1 Retention Time Database - September 5, 1989 Sorted by Carpourd Nams RT (min) CMPD ----------- 6 DBWAX DB1 COMPOUND NAME MY CAS Nl1M6ER .... ..... ..... ....................................................................... .... .------•----- 151 51.9 72.7 PYRROLE-iH, 2-ACETYL-5-NETHYL- 123 6982-72-S 1694 60.1 PYRROLE-IH, 2-ACETYL-N-FURANYLMETHYL- 189 13678-73-4 577 PYRROLE-IH, 2-METHYL- 81 636-41-9 1088 PYRROLE-IH, 3,4-DIMETHYL- 95 822-S1-S 1513 77.1 PYRROLE-1H, 3-ACETYL- 109 1072-82-8 479 77.1 PYRROLE-1H, 3-ACETYL- 109 1072-82-8 305 34.9 PYRROLE-1N, 3-ACETYL-1-METHYL- (SW158D ) 123 932-62-7 634 PYRROLE-1H, 3-ACETYL-N-ETHYL- (SYW174D) 137 1097 PYRROLE-1H, 3-ETHYL-4-METNYL- 109 488-92-6 407 PYRROLE-1H, N-ACETYL-1,2-DINYDRO- (SW2 43D) 111 2310S-S8-0 575 PYRROLE-1H, N-ETHYL- 95 617-92-5 1518 53.6 PYRROLE-1H, N-(2-PHENYLETNYL)- 171 S0691-29-7 1590 54.6 PYRROLE-1H, N-(2-PYRIDYLNETHYL)- 158 78210-51-2 348 PYRROLE-1H, N-(2-PYRIDYLNETHYL)- (S{A1205D) 1S8 78210-51-2 1585 61.9 PYRROLE-1H, N-(3-PYRIDYLNETHYL)- 158 80866-95-1 390 PYRROLE-iH-2-CARBONITRILE, 5-METNYI- (SBB233) 106 26173-92-2 796 50.7 PYRROLE-1H-2-CARBOxAIDEHYDE 95 1003-29-8 381 PYRROLE-IH-2-CARBOXALDEHYDE 95 1003-29-8 382 PYRROLE-1H-2-CARB00(ALDEHYDE, S-NETHYL- 109 1192-79-6 797 PYRROLE-1H-2-CARB00(ALDEHYDE, S-METHYL- 109 1192-79-6 1471 PYRROLE-1H-2-CARBODUILDEHYDE, N-Fl1RA11YLMETHYL- 175 13788-32-4 374 PYRROLE-1H-2-CARBOXALDEHYDE, N-METHYL- 109 1192-58-1 1472 PYRROLE-iH-2-CARBORALDEHYDE, N-(3-METNYLBUTYL)- 165 13678-79-0 1470 PYRROLE-1H-2-CARBOxALDEHYDE-1H, 1-ETNYL- 123 2167-14-8 1567 85.1 PYRROLE-1H-2-CARBODCAMIDE (SNN118D) 110 4551-72-8 764 PYRROLE-1H-2-CARBOXAMIDE (SNN118D) 110 4SS1-72-8 664 PYRROLE-1H-2-CARBOXYLIC ACID 111 634-97-9 741 55.8 PYRROLE-1H-2-CARBOXYLIC ACID, 5-METHYL, ETHYL ESTER 153 3284-S1-3 742 PYRROLE-1H-2-CARBONYLIC ACID, 5-METHYL, METHYL ESTER 139 1194-97-4 1516 54.4 PYRROLE-1H-2-CARBOXYLIC ACID, 5-METHYL-, METHYL ESTER 139 1194-97-4 426 PYRROLE-iH-2-GLYOXYALDENYDE (SW224D) 123 72693-01-7 389 PYRROLE-IH-3-CARBONITRILE 92 7126-38-7 383 54.1 PYRROLE-IH-3-CARBOXALDEHYDE, 2-METHYL- 109 17619-39-S 798 PYRROLE-1H-3-CARBOD(ALDEHYDE, 2-METHYL- 109 17619-39-5 422 PYRROLE-1H-3-CARBOXALDEHYDE, 5-ETNYL- (SWY226D) 123 78210-62-5 1498 71.3 PYRROLE-1H-3-CARBOD(YLIC ACID, 2-METHYL-, ETHYL ESTER 153 936-12-9 1724 37.2 PYRROLE-2,5-DIONE, 1,3-DINETNYL-4-ETNYL- (MALEIMIDE, 1,3-DIMETNYL-4-ETHYL-) 155 770 PYRROLE-2,5-DIONE, 3,4-DIETNANOL-1-METHYL- (MALEIMIDE, 3,4-DINYDROxVMETHYL-N 171 61892-71-5 771 PYRROLE-2,5-DIONE, 3,4-DIMETHYL- (MALEINIDE,3,4-DIMETHYL-) 125 17825-86-4 1723 36.6 PYRROLE-2,5-D10NE, 3-ETHYL-I-METHYL- (MALEIMIDE, 3-ETHYL-N-METHYL-) 139 15542-97-9 1727 57.8 PYRROLE-2,5-DIONE, 3-METNYL- (NALEINIDE, 3-METNYL-) III S61S-90-7 1372 PYRROLE-2,5-DIONE-1N, 1-ETHYL- (MALEIMIDE, N-ETHYL-) 12S 128-53-0 21 PYRROLE-2,5-D10NE-1N, 3-ETHYL- (MALEIMIDE, 3-ETHYL-) 111 1072-87-3 28 56.3 PYRROLE-2,5-DIONE-1N (MALEIMIDE) 97 541-59-3 400 PYRROLE--1H-2-CARBODULDEHYDE, 5-HYDRO0(YMETNYL-N-METHYL- 139 29813-44-3 1371 PYRROLE[1,2a]PYRA2INE, 3,6-DINETHYL- 146 2155 39.4 PYRROLIDIINONE-2, 1-ETHENYL- 111 88-12-0 1149 5.3 30.8 PYRROLIDINE 71 123-75-1 1152 PYRROLIDINE, 1-BUTYL- 127 767-10-2 1150 PYRROLIDINE, 1-ETNYL- 99 733S-06-0 939 30.2 PYRROLIDINE, 1-Ft1RANYLMETHYL- (SR209D) 151 61893-12-7 1153 2.2 30.8 PYRROLIDINE, 1-METHYL- 85 120-94-S 831 PYRROLIDINE, 1-METHYL-4-OXO-2-(2-0)(OPROP YL)- (SR174D) 15S 61892-89-5 1155 PYRROLIDINE, 1-PROPYL- 113 7335-07-1 1379 PYRROLIDINE, 1-(1-OXOBUTYL)- 141 33527-93-4 1651 67.8 PYRROLIDINE, 1-(2-FURANYLCARBONYL)- 16S 78504-0S-9 832 PYRROLIDINE, 1-(2-OXOPROPYL)- (SR199D) 141 61892-90-8 1850 46.6 PYRROLIDINE, 1-(3-NETHYL-1-0)(OBUTYL)- 155 60026-17-7 208 PYRROLIDINE, 1-(3-NETHYL-I-OXOBUTYL)- 15S 60026-17-7 1708 47.3 PYRROLIDINE, 1-(3-METHYL-1-OXOBUTYL)- 155 60026-17-7 1652 71.6 PYRROLIDINE, 1-(S-METHYL-2-FURAIIYLCARBON YL)- 179 940 33.8 PYRROLIDINE, 1-(S-METHYL-2-FURANYLMETNYL )- (SR2100) 165 61480-99-7 2046 38.2 PYRROLIDINE, 2,5-DIMETHYL- 99 3378-71-0 1151 39.1 PYRROLIDINE, 2,5-DINETHYL- 99 3378-71-0 1156 PYRROLIDINE, 2-ETHYL-I-METHYL- 113 . 857 PYRROLIDINE, 2-HYDROXYMETHYL-5-NETNYL- (SL100D) 115 281/S-37-9 1154 PYRROLIDINE, 2-METHYL- 85 765-38-8 375 43.0 PYRROLIDINE, N-ACETYL- - 113 4030-18-6 376 PYRROLIDINE, N-FORMYL- (PYRROIIDINECARBODUILDEHYDE-1) 99 3760-54-1 1473 PYRROLIDINE, N-FORMYL-2-METHYL- 113 78914-62-2 1994 39.9 65.5 PYRROLIDINECARBONITRILE-1 96 1S30-88-7 46

TOBACC0.WK1 Retention Tim Database - Septewber 5, 1989 Sorted by Capourd NaBe RT (min) CMPD ----------- B DBWAX DB1 (MiPOINJD NAME N1 CAS NIRBER ---- ----- •---- ----------------------------------------------------------------------- ---- ............. 1851 39.1 PYRROLIDINECARBOXALDEHYDE-1 (PYRROLIDINE, N-FORMYL-) 99 3760-54-1 1474 PYRROLIDINECARBOD(ALDEHYDE-2 99 61480-98-6 778 45.7 64.4 PYRROLIDINE-2,5-D10NE, 1-METHYL- (SUCCINIMIDE, N-METHYL-) 113 1121-07-9 1373 PYRROLIDINE-2,5-DIONE, 3-ETHENYL-4-METHYL- (SUCCINIMIDE, 3-ETHENYL-4-METHYL- 139 774 74.1 PYRROLIDINE-2,5-DIONE, 3-ETHYLIDENE- (SR1150) 125 14156-12-8 212 71.6 PYRROLIDINE-2,S-D10NE, 3-ETHYLIDENE-4-METHYL- 139 16395-79-2 775 52.8 PYRROLIDINE-2,5-DIONE, 3-ETHYLiDINE-N-METHYL- (SUCCINIMIDE, 3-ETHYLIDENE-N-M 139 61892-74-8 1374 3-ETHYL-3-METHYL-) 141 3-ETNYL-3-METNYL- (SUCCINIMIDE PYRROLIDINE-2 5-DIONE 77-67-8 777 , , , PYRROLIDINE-2,5-DIONE, 3-ETNYL-4-METHYL- (SUCCINIMIDE, 3-ETHYL-4-METHYL-) ( 141 S8501-92-1 776 PYRROLIDINE-2,5-DIONE, 3-ETHYL-N-METNYL- (StK:CINIMIDE, 3-ETHYL-N-METNYL-) ( 141 15542-97-9 211 PYRROLIDINE-2,5-DIONE, 3-METHYL- (SUCCINIMIDE, 3-ETHYL-) 127 58467-27-9 773 PYRROLIDINE-2,5-DIONE, 3-METHYL- (SUCCiNIMIDE, 3-METHYL-) (SNN 77D) 113 5615-90-7 1375 PYRROLIDINE-2,5-DIONE, 3-(1-METHYLETHYU- (StJCCINIMIDE, 3-(1-METHYLETHYL)-) 141 72693-03-9 1376 45.3 PYRROLIDiNE-2,5-DIONE, 3-(1-METHYLETHYL)-N-METHYL- (SUCCINIMIDE,3-(1-METHYLE 155 15S42-99-1 1377 PYRROLIDiNE-2,5-DIONE, N,3,4-TRIMETNYL- (SUCCINIMIDE, N,3,4-TRIMETHYL-) 141 71099-03-1 207 42.0 PYRROLIDINE-2,5-DIONE, N,3,DIMETHYL- (SUCCINIMIDE, N,3-DIMETHYL-) 127 15542-96-8 772 PYRROLIDINE-2,5-DIONE (SUCCINIMIDE) 99 123-56-8 391 29.6 PYRROLIDINE-N-ACETONITRILE (SBB1970) 110 29134-29-0 2018 76.5 PYRROLIDINE-N-BUTYRONITRILE 138 35543-25-0 52 51.8 PYRROLIDINONE-2 85 616-45-5 1536 51.8 PYRROLIDINONE-2 85 616-45-5 1378 36.6 PYRROLIDINONE-2, 1,S-DIMETNYL- 113 40 PYRROLIDINONE-2, 1,5-DINETHYL- 113 5075-92-3 1849 38.5 PYRROLIDINONE-2, 1-ETHENYL- 111 88-12-0 1825 37.8 67.6 PYRROLIDINONE-2, 1-ETHYL- 113 2687-91-4 1852 35.7 62.0 PYRROLIDINONE-2, 1-METHYL- 99 872-50-4 790 34.9 62.0 PYRROLIDINONE-2, 1-METHYL- 90 872-50-4 1380 PYRROLIDINONE-2, 1-(2-ONOETHYL)- 127 1980 50.7 66.1 PYRROLIOINONE-2, 3-METHYL- 99 2555-05-7 1987 50.9 66.1 PYRROLIDiNONE-2, 5-METNYL- 99 108-27-0 -288 50.7 66.0 PYRROLIDINON€-2, 5-M€TNYL- -99 108-27-0 1148 PYRROLINE-1 (PYRROLE-2H, 3,4-DIHYDRO-) 69 5724-81-2 1147 PYRROLINE-2 (PYRROIE-iN, 2,3-DIHYDRO-) 69 638-31-3 833 PYRROLINE-3, 2-ACETYL-3,4-DIMETHYL- (SR45D) 139 61891-76-7 1146 7.0 PYRROLINE-3 (PYRROIE-1N,2,5-DIHYDRO-) 69 109-96-6 1693 53.7 PYRROLIZINE-1H, 5-ACETYL-2,3-DINYDRO- 149 S5041-85-5 1701 60.0 PYRROLIZIN(1H)-1-ONE, 2,3-DIHYDRO- 121 17266-64-7 791 PYRROLONE-2(1H), 2,3-DIHYDRO-S-(3-PYRIDYL)- (SL21D) 160 62003-47-8 240 53.7 PYRROLONE-2(2H), 1,5-DIHYDRO-1-ACETYL-3-ETHYL-4-METHYL- 167 61892-80-6 1669 55.2 PYRROLONE-2(2H), 1,5-DIHYDRO-1-ACETYL-4-ETHYL-3-METHYL- 167 416 PYRROLONE-2(2H), 1,5-DIHYDRO-1-METHYL-5-(1-METHYLETHYLIDINE)- 137 78210-72-7 238 60.4 PYRROLONE-2(2H), 1,5-DINYDRO-3,4,5-TRiMETNYL- (SWW4D) 125 4030-23-3 200 PYRROLONE-2(2H), 1,5-DINYDRO-3,4-DIMETHYL- 111 4030-22-2 1568 62.3 PYRROLONE-2(2H), 1,5-DIHYDRO-3,4-DIMETHYL- 111 4030-22-2 289 PYRROLONE-2(2H), 1,5-DiHYDRO-3,5-DIMETHYL- (SWW68D) 111 51088-90-5 488 PYRROLONE-2(2H), 1,5-DIHYDRO-3,S-DIMETHYL-4-ETHYL- (SR158D) 139 4030-24-4 1381 PYRROLONE-2(2H), 1,5-DINYDRO-3-ETHYL-4,S-DIMETHYL- (SR158D) 139 489 PYRROLONE-2(2H), 1,5-DIHYDR0-3-ETHYL-4-METHYL- (SR60D) 125 766-36-9 414 PYRROLONE-2(2H), 1,5-DIHYDRO-3-ETHYL-5-METHYLENE- (SWW237D) 123 78210-71-6 793 PYRROLONE-2(2H), 1,5-DIHYDRO-3-METHYL- (SL1D) 97 27406-77-S 1382 PYRROLONE-2(2H), 1,5-DIHYDRO-4-ETNYL-3,5-DIMETHYL- 139 4030-24-4 792 65.7 PYRROLONE-2(2H), 1,5-DINYDRO-4-ETRYL-3-METBYL- (SR61D) 125 766-45-0 187 PYRROLONE-2(2H), 1,5-DIHYDRO-4-METNYL- 97 53598-99-5 22 60.1 PYRROLO-2,5-DIONE-(iH), 3-ETHYL-4-METHYL- 139 20189-42-8 265 PYRROLO[1,2a]PYRAZINE (SYW58D) 118 274-45-3 608 PYRROLO[1,2a]PYRAZINE (SWW58D) 118 274-45-3 263 PYRROLO[1,2a]PYRAZINE-1,4-DIONE, NEXANYDRO- (SWW47) 154 19179-12-5 941 3-D10NE-1H, NEXAHYDRO- (SR240D) PYRROLO[1 2C]IMIDAZOLE-1 140 5768-79-6 1348 92.1 , , PYRROLO[1,2-c]IMIDAZOLE-1,3(2H)-D10NE, TETRAHYDRO- (PROLINE HYDANTOIN, SR240 140 5768-79-6 557 66.1 67.9 PYRROLO[2,3b]PYRIDINE-1H 118 271-63-6 556 1-METHYL- (SBB163D) 132 PYRROLO[2 3b]PYRIDINE-1H 27257-15-4 552 , , PYRROLO[2,3b]PYRIDINE-1N, 2-METHYL- (588137D) 132 23612-48-8 551 PYRR0L0[2,3b]PYRIOINE-1H, 9-ETHYL- (SBB141D) 146 78249-85-1 553 PYRROLO[2,3b]PYRIDINE-1H, 7-METHYL- (5861380) 132 72692-80-9 554 PYRROLO[2,3b]PYRIDINE-1H, ?-METNYL- (SBB139D) 132 555 PYRROLO[2,3b]PYRIDINE-1H, ?-METHYL- (SB61400) 132 1191 GUINAZOLINE, 2-METHYL- 144 700-79-8 627 GUINAZOLINE, 4-METHYL- (SBB1880) 144 700-46-9 626 48.8 79.1 GUINAZOIINE (SBB162D) 130 253-82-7 84 48 7 QUINOLINE 129 91-22-5 625 . GUINOLINE, 1,2,3,4-TETRAHYDROMETHYL- (SBB156D) 147 78249-82-8 47

„ 1 TOBACCO.WK1 Retention Time Database - Septeaber 5, 1989 Sorted by Compoisd Name RT (min) CMPD ----------- # DBYAx D61 C01(POUIID NAME ---- ----- ----- ------------~-~-;------------------------------------------------------ 624 GUINOLINE 1 2 3 4-TETRANYDRONETHYL- (568160D) 1855 51.8 QUINOLINE, 1,2,3,4-TETRANYDRO- 568 QUINOLINE, 2,3,8-TRINETHYL- (566243D) 1040 QUINOLINE, 2,4-DINETHYL- 558 QUINOLINE, 2,6-DIHETHYL- (SBB257D) 561 QUINOLINE, 2,8-DINETHYL- (566230D) 563 OUINOLiNE, 2-ETHYL- (5682420) 566 GUINOLINE, 2-ETHYL-5,6,7,8-TETRANYDRO- 1072 QUINOLINE, 2-METHOXY- 1041 QUINOLINE, 2-METHYL- 571 40.0 QUINOLINE, 2-NETHYL-5,6,7,8-TETRANYDRO- (SBB189D) 1035 OUINOLINE, 2-(1-METHYLETHYL)- 418 QUINOLINE, 2-(3-PYRIDYL)- (SW229D) 1037 QUINOLINE, 3-ETHYL- 1073 QUINOLINE, 3-METHOXY- 1043 QUINOLINE, 3-NETHYL- 564 QUINOLINE, 4-ETHYL- 1042 54.7 QUINOLINE, 4-METHYL- (LEPIDINE) 1034 QUINOLINE, 4-(1-HETNYLETNYL)- 572 QUINOLINE, 5,6,7,8-TETRANYDRO- (566207D) 562 GUINOLINE, 5,8-DINETHYL- (S8B231D) 565 QUINOLINE, 5-ETHYL- 1032 QUINOLINE, 6-BUTYL- 1071 65.4 QUINOLINE, 6-METH01(Y- 1045 GU1NOLiNE, 6-METHYL- 1031 QUINOLINE, 7-BUTYL- 1038 QUINOLINE, 7-ETNYL- 1075 QUINOLINE, 7-METHONY- 1044 OUINOLINE, 7-METHYL- 1036 QUINOLINE, 8-ETHYL- 1074 QUINOLINE, 8-NETHOXY- 569 48.9 QUINOLINE, 8-METHYL- (SB6241D) 1033 QUINOLINE, 8-PROPYL- 1039 QUINOLINE, C2-ALKYL- 560 QUINOLINE, C3-ALKYL- (SBBI7TD) 559 GUINOLINE, DINETHYL- ,(SBB173D) 961 QUINOLINE, h-BENZO- 567 QUINOLINE, ?-ETHYL-5,6,7,8-TETRAHYDRO- 570 QUINOLINE, ?-METHYL-5,6,7,8-TETRAHYDRO- (588190D), 394 QUINOLINE-5-CARBONITRILE (566180D) 341 QUINOLINE-6-OR-7-CARBONITRILE (CAS # FOR 7-CARBONITRILE IS 67360-38-7) 2144 47.3 OUINOLINE-D7 1890 56.5 OUINOLINOL-8 160 45.8 GUINOXALINE 170 52.4 QUINOXALINE, 2,3-DINETHYL- 1125 QUINOXALINE, 2-ETNYL- 611 QUINOXALINE, 2-METHYL- (SB6254D) 612 41.6 OUINOXALINE, 2-METHYL-5,6,7,8-TETRAHYDRO- (566208D) 1312 OUINOXALINE, DIHYDRO- 609 QUINOXALINE, DINETHYL- (568174) 613 QUINOXALINE, TRINETHYL- 610 QUINOXALINE, ?-NETHYL- 1127 QUINOZALINE, 2-ETHYL-3-METHYL- 2165 90.0 78.8 RESCORCINOL 1778 20.9 ROSE OXIDE (ISOMER OF #1776) 1777 20.9 ROSE OXIDE (ISOMER OF #1776) 1582 58.5 SBB126 227 SBB138D 1824 91.5 SCLARIOLIDE 1421 SL29C 136 60.4 Sll30C 789 SR179D 1424 SR268C (ISOMER OF /1423) 60 67.9 SR43C 63 43.5 SR51C 705 46.2 SR53D 1618 49.7 SR60C 2078 13.0 41.7 STEREOISONER OF #2077 2088 39.3 78.0 STEREOISOMER OF 62087 1314 STILBENE, 2-AMINO- 745 SUGAR ANHYDRIDE (SR166D) MW CAS NIMBER ---- ------------- 147 78249-82-8 133 635-46-1 171 4945-28-2 157 1198-37-4 157 877-43-0 157 1463-17-8 157 1613-34-9 161 5671T-33-0 159 6931-16-4 143 91-63-4 147 2617-98-3 171 17507-24-3 206 6294-65-1 157 1873-54-7 159 6931-17-5 143 612-58-8 15T 19020-26-9 143 491-35-0 171 17507-25-4 133 10500-57-9 157 2623-50-9 1S7 65745-66-6 185 7634-74-4 159 5263-87-6 143 91-62-3 185 157 7661-47-4 159 4964-76-5 143 612-60-2 157 19655-56-2 159 938-33-0 143 611-32-5 171 7661-53-2 157 171 157 179 230-27-3 161 78249-84-0 147 78249-83-9 154 S9551-02-9 154 23395-72-4 136 14S 148-24-3 130 91-19-0 158 2379-55-7 158 144 72S1-61-8 150 38917-65-6 132 64811-58-1 158 72692-77-4 172 72692-78-5 144 64828-56-4 172 37920-99-3 110 108-46-3 154 154 196 132 250 564-20-5 178 16825-04-0 219 140 128 254 212 52812-41-6 144 208 20194-67-6 102 565-60-6 154 619-01-2 195 13066-19-8 174 48

TOBACCO.WK1 Retention Tiae Database - Septeaber S, 1989 RT (min) CNPD ----------- # DBWAX DB1 Sorted by Cc.pard Name COlIPOUND NAME ----------------------------------------------------------------------- IR1 CAS NUBER 744 Sl1GAR DERIVATIVE ACETATE (SR187D) 188 743 SUGAR DIANHYDRIDE ACETATE (SR151D) 186 863 SUGAR DIANHYDRIDE (1,6:2,3-beta-D-TALOSE) 144 870 SUGAR DIANHYDRIDE (SL9D) 146 866 SUGAR DIANHYDRIDE (SNN106D) 144 862 SUGAR DIANHYDRIDE (SR110D) 144 861 SUGAR DIANHYDRIDE (SR127D) 144 860 SUGAR DIANHYDRIDE (SRISOD) 144 868 SUGAR DIANHYDRIDE (SR153D) 146 864 SUGAR DIANHYDRIDE (SR165D) 144 865 SUGAR DIANHYDRIDE (SR168D) 144 867 SUGAR DIANHYDRIDE (SR177D) 146 869 SUGAR DIANHYDRIDE (SR184D) 146 871 SUGAR DIANHYDRIDE (SR185D) 146 859 SUGAR DIANHYDRIDE (SR44D) 144 858 SUGAR DIANHYDRIDE (SR47D) 144 633 SWW141D 234 587 SWY145D 208 635 SWW162D 222 243 SWW18D 155? 355 SIA1202D 183 349 SWW206D (NICOTINE LIKE) 158 244 SWW20D 134 399 SWW253D 174 287 SWW67D, NITROGEN COMPD. WITH CARBONYL 114 1791 51.8 TERADECANOIC ACID, ETHYL ESTER (MYRISTIC ACID, ETHYL ESTER) 256 124-06-1 2204 66.2 TETRACOSANE 338 646-31-1 1475 47.7 100.3 TETRADECANAL 212 124-25-4 5 9 2 198 629-59-4 1950 1846 22. 22.5 . TETRADECANE 8 89.2 TETRADECANE (C14 HYDROCARBON) 198 629-59-4 2153 51.5 TETRADECANOIC ACID, NETHYL ESTER 242 124-10-7 30 TETRADECANOIC ACID (NYRISTIC ACID) 228 544-63-8 1858 75.3 TETRADECANOIC ACID (MYRISTIC ACID) 228 544-63-8 2177 57.7 103.2 TETRADECANOL-1 214 112-72-1 . 834 TETRALONE-1 146 529-34-0 1242 14.5 THIAZOLE 85 288-47-1 497 21.6 THIAZOLE, 2,4,5-TRINETHYL- (SBB220D) 127 13623-11-5 1252 16.7 THIAZOLE, 2,4-DINETHYL- 113 541-58-2 1248 THIAZOLE, 2,4-DIMETHYL-S-ETHYL- 141 38205-61-7 1253 THIAZOLE, 2,5-DINETHYL- 113 4175-66-0 1254 THIA20LE, 2-ETHYL- 113 15679-09-1 492 THIAZOLE, 2-ETHYL-5-METHYL- (SBB224D) 127 19961-53-6 1249 THIAZOLE, 2-METHYL- 99 3581-87-1 490 THIAZOLE, 4,5-DIMETHYL- (SB6218D) 113 3581-91-7 480 THIAZOLE, 4-ACETYL- 127 38205-66-2 493 THIAZOLE, 4-ETHYL-2-METHYL- (SBB225D) 127 32272-48-3 494 THIAZOLE, 4-ETHYL-S-METHYL- (SB8222D) 127 52414-91-2 1250 THIAZOLE, 4-METHYL- (SBB105D) 99 693-95-8 496 THIAZOLE, 4-PROPYL- (SBB223D) 127 41981-60-6 491 THIAZOLE, 5-ETHYL- (SBB219D) 113 17626-73-2 1247 THIAZOLE, 5-ETHYL-2-METHYL- 127 19961-52-5 495 THIA20LE, 5-ETHYL-4-NETHYL- (SBB221D) 127 31883-01-9 99 3581-89-3 1251 959 THIAZOLE, 5-NETHYL- THIOPHENE, 1,1-D10XIDE-TETRAHYDRO- (SWW66D) 120 126-33-0 1357 THIOPHENE, 2-ACETYL-2,3-DIHYDRO- 128 2117 8.0 40.4 THIOPHENE, 2-METHYL- 98 554-14-3 1476 35.8 THIOPHENECARBOXALDEHYDE-2 112 30583-13-2 126 5834-16-2 800 1477 41.4 THIOPHENECARBODUILDEHYDE-2, 3-HETHYL- THIOPHENECARBOXALDEHYDE-2, 5-METHYL- 126 13679-70-4 32 85.5 TRIACONTANE (HYDROCARBON C30) 422 638-68-6 2131 85.5 TRIACONTANE (HYDROCARBON C30) 422 638-68-6 256 TRIAZINE-1,3,5, 1,4-DIHYDRO-1,2-DIMETHYL- (SWW38D, PROPOSED) 111 2206 86.2 TRICONTANE 422 2203 62.7 TRICOSANE 324 638-67-5 1478 42.7 94.4 TRIDECANAL 198 10486-19-8 1951 18.9 83.1 TRIDECANE 184 629-50-5 2176 53.7 97.9 TRIDECANOL-1 200 112-70-9 1479 TRIOXANE-1,3,5, 2,4,6-TRIMETHYL- 132 123-63-7 1764 32.3 82.0 UNDECANAL 170 112-44-7 1953 9.4 69.3 UNDECANE 156 1120-21-4 1886 64.0 UNDECANOIC ACID 186 112-37-8 49

6 1 f TOBACCO.YK1 Retention Tiwe Database - Septeaber S, 1989 Sorted by Cowpouid NaAe RT (min) CMPD ----------- 0 DBYAX DB1 CONPOUIR) NAME MY CAZ NIMBER ---- ----- ----- ----------------------------------------------------------------------- --.. .............. 1765 45.4 86.5 tINDECANOL-1 172 112-42-5 196 36.1 UNDECAN-2-ONE, 6,10-DINETHYL- (GERANYL ACETONE, TETRAHYDRO-) 198 1604-34-8 1729 36.7 UNDECAN-2-ONE, 6,10-DINETHYL- (TETRANYDROGERANYL ACETONE) 198 1604-34-8 45 UNDECA-5,9-DIEN-2-ONE, 6,10-DINETHYL- (GERANYL ACETONE) 194 3796-70-1 2065 10.4 68.0 UNDECENE-1 154 821-95-4 1634 URACIL, 3,5-DIMETHYL-, (PYRIMIDINE-2,4-DIONE(1H,3H), 3,5-DIMETHYL-) (SR163D) 140 -4160-n-4 1385 UREA 60 57-13-6 2148 6.8 WATER 18 7732-18-5 50

APPENDIX 2 - The SEARCH Macro . . .. v NAME LOOK CLEAR FILE THRESHOLD STARTSET TABULATE HEADER,#6 TIC GETSCALARS DRAW 3,X „ YLOW:YHIGH SCREENPRINT CLEAR INTEGRATE TABULATE RESULTS,#6 ENDSET N=1 WHILE N<= NPEAKS WRITELN 701,#12#13 PEAK N PEAK N,START Y AB=RET_TIME SUBTRACT SUPPRESS NORMALIZE 1000 DRAW 1,X „ 0:1200 SCREENPRINT TABULATE ,#6 TOF GETS POINT, -AB-0.5:AB+0.5,Y DRAW 1,Y,AB-0.5:AB+0.5, -YLOW:1.2*Y SCREENPRINT CLEAR IF L=1 THEN SEARCH TOBACCO.L TABULATE RESULTS ,#6 RETRIEVE 1,2,3 MERGE NORMALIZE 1000 FORMAT SEPARATED DRAW 3 SCREENPRINT CLEAR CLEAR X ENDIF IF L=2 THEN SEARCH NBS_REVE.L TABULATE RESULTS ,#6 RETRIEVE 1,2,3 MERGE NORMALIZE 1000 FORMAT SEPARATED (cont'd in next col.) DRAW 3 SCREENPRINT CLEAR CLEAR X . 51 ENDIF IF L=3 THEN PBMSEARCH NBS_REVF.L TABULATE RESULTS ,#6 GETS RESULTS,X M=NUM_HITS IF M>=3 THEN RETRIEVE 1,2,3 MERGE NORMALIZE 1000 FORMAT SEPARATED DRAW 3 SCREENPRINT CLEAR CLEAR X ENDIF IF M=2 THEN RETRIEVE 1,2 MERGE NORMALIZE 1000 FORMAT SEPARATED DRAW 3 SCREENPRINT CLEAR CLEAR X ENDIF IF M=1 THEN RETRIEVE 1 MERGE NORMALIZE 1000 FORMAT SEPARATED DRAW 3 SCREENPRINT CLEAR CLEAR X ENDIF IF M<1 THEN MESSAGE NO MATCHES - FOUND FOR THIS PEAK SCREENPRINT CLEAR CLEAR X ENDIF ENDIF ROLL -1 N=N+1 ENDWHILE CLEAR X MESSAGE ANALYSIS COMPLETE