Tobacco Documents Online

RACIJJI62C 24th March, ]981 .. FLAVOUR DEGRADATION STUDIES REVIEW MEETING I. 2. 3e 4. 5. Present: Mr. A.G. Barnes Dr. P.O. ~van Dr. R.A. Crellin Mr. T.G. Mitchell Dr. P.S. Stewart. In the near future, screening work involving cembratrienediol (CBD), manool, ambroxide, 8-1onone and ambrettolide will be complete. The reproducibility of the system will be assessed by rescreening selected organisms. Larger scale reaction with organisms which cause high conversion of substrate into a small number of products will then be carried out. Product mixtures will be passed to PCB/PSS for Prep/SemlprepLC into product materials for identification by nmr and ms. LC work will be time consuming and requires either: a] an extra palr of skilled hands or b) a temporary halt to other project work. Screening of organisms against 8-carotene and re-screening against abienol is Justified. Solvent problems may be encountered with B-carotene and Vitamin A acetate may he substituted. Evidence to date suggests that primary reaction due to micro-organisms is hydroxylation. Consequently, two-step approach may be adopted as follows: BATCo document for Legal Services • Health Canada 20 May 1999

- 2- (i) B-Carotene mtcrob¢o ~ Lutein etc. ~ photoche~ Bydroxylonones, Hydroxydamascones etc. (ii) Abienol microbio Hydroxyabienol ~ pho~x~.hem Novel series of ~droxynorlabdanolds. This is appealing, since literature information is that hydroxy derlvatlves are more tobacco-llke and have lower flavour thresholds. 6, 7b 8, Ketolsophorone ks available and should be screened. The normal position of reaction is blocked and this might induce other reaction types. Crombie (Notts. Univ.} might be approached to consider chemical routes to hydroxy derivatives. Cambie/Grant (N.Z.) should be approached for norlabdanes which they have synthesised. If available, these would add to our understanding of the underlying structural features which convey tobacco flavour. 9. Next meeting April 27th, Distribution: Mr. A.G. Barnes. Dr. P.C. Bevan. Mr. T.G. Mitche11. Dr. P.S. Stewart. lO.30ata. R.A. CRELLIN CD BATCo document for Legal Services • Health Canada 20 May 1999

Dr. P.C. Bevan/Mr. A.G. Barnes/AH/62C 3rdMarch, 1982. B I 0 L 0 G I C A L-C H E M I C AL C 0 L LAB 0 EAT I 0 N PROGRESS MEETING - 2NDMARCH 1982 Present: Mr. A.G. Barnes Dr. P.C. Bevan Mr. D.A. Johnson The meeting was convened to review p~ogress todate and to agree the work progr~z~e for the next few months. A. PLANT CELL CULTURE WORK / U-CBD when fed to a Palotina plant cell culture (ex Sheffield) gave a number of more polar products. These will be looked at by GC and GC-MS. The following experiments will be run next: u-CBD with Izmir and NC2326 B-CBD with Izmir, NC2326 and Palotina In addition (12Z)-abienol could be examined, although this compound is inherently less stable to heat and light and thus presents handling problems. B. MICROBIAL DEGRADATION WORK Achieved to Date i) DeEradation of sclareol to three products in good yield. No further work planned on this compound. ii) Degradation of 8-1onone to a range of Cl$ and Cll compounds. The CIs compounds, some of which are knownaroma compounds, have also been obtained by Japanese workers (JTS) but the CII co~potmds are novel. However they do not seem to be of great potential as tobacco flavourants. Do not plan to pursue this further. iii) Degradation of u-lonone has recently been started. The initial product is a-ionol. The reduction will very possibly be stereoselective, which would differentiate it from the (easily performed) chemical reduction. v~o BATCo document for Legal Services • Health Canada 20 May 1999

-2- iv) Degradation of a-CBD to more polar products. Two of these have been identified by spectroscopic techniques as I and ~I. (I is a known tobacco constituent, while II is a new compound.) v) B-CBD, Ambroxide, Ambrettolide and manool have been screened and promising organisms have been identified. Next Steps i) The ~-ionone degradati~n~rill be allowed to progress further and will be monitored bY GC to determine the optimum time at which to halt the fermentation. Products ~ill be separated and tested on cigarettes. 3-0xo-~-ionone (obtained from B.A.T. Hamburg) is available as a reference compound to aid identification. ii) B-CBD will be degraded and products identified, to complement the results alrady obtained from the ~-isomer. (Screening already carried out.) Organism: ¥310. iii) The potent aroma compound ambroxide willbe degraded to products in which it is hoped the aroma will be intensified/ f?l~ modified. (Screening already done.) Orsanism will be E3~e and/or F318. iv) Another diterpenold of potential use is man~ol; F318 will be used initially. A.G. BARNES P.C. BEVAN Distribution Mr. A.G. Barnes Mr. M.A. Baylis Dr. P.C. Bevah PCB/AGB/AH/62C 3rd March, 1982. Dr. E.A. Crellln Mr. D.A. Johnson Mr. T.G. Mitchell r~D r~c BATCo document for Legal Services • Health Canada 20 May 1999

.~ o~v,c~S / I K :E P,j P~j r,,j r,~ BATCo document for Legal Services • Health Canada 20 May 1999