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CHARGE NUMBER: 2525 PROJECT TITLE: Chemistry and Isolation of Tobacco Constituents PROJECT LEADER: H. J. Grubbs PERIOD COVERED: July 1 - 31, 1981 DATE OF REPORT: August 7, 1981 It has been reported that the essential oil of Kudzu_ (Puerari'a lobata) contains a number of valuable tobacco flavorant compounds..' The steam distillate of aged Kudzu leaves has been shown to contain damascenone Q), megastigmatrienones (~), 3-hydroXy-S-damascone (ti3), and substituted guaiacols. 0 % qip Q) E, Z isomers A program has been initiated in conjunction with Rett Southwick to further i:nvestigate the composition of the essential oil and to determine the applicability of Kudzu extract as a source of tobacco flavorants. The composition and odor properties of the essential oil of green Kudzu leaf are under current investigation. Odor evaluation of two essential oil samples obtained by extraction2 and/or steam distillation2a3 are very similar. The odor profile is very reminiscent of green tobacco or tea. Those essential oil samples are currently being examined by chromatographic and' spectroscopic means.3 Additional harvests of Kudzu leaves will be made at intervals during the summer and fall to determine the variation in the composition and quantity of essential oil. Odor profiles and'subjective evaluations are planned. A request was made by Project 2501 for additional samples of 14C- menthol. The remnants of two previous chamber runs of l''C-mint plants were combined and purified by preparative HPLC to yield'.a total of 75NCi of pure '"C-menthol.'`

-2- Ii I F E C I A mixture of the mono menthyl esters of ineso and A 2,3-dimethyl- succi,nlc aci.d$ (,4) was partially separated using reverse phase HPLC.5 0 H- H-C-O-.Zmen - H3 3 .. (4)d,.2, and me.ao i'somers This group of esters has shown to have utility as pyrolytic precursors of menthol. The resolution of the geometric isomers and subsequent pyrolysis wi:ll provide a better understanding into the mechanism of thermal generation of menthol. Several new methods of isollation and quantitation of_ tobacco alkaloids are currently being developed. In conjunction with Project 2506, four different cultivars of tobaccohave been grown under "C02 chamber conditions. TLC'and HPLC techniques are currently being developed.to rapidly quantitate 1''C-nicotine and the minor alkaloids. These same procedures are also being evaluated as preparative procedures.s1s,, 1. S. Shibate et al.; Agric. Biol. Chem., 42(1), 195-197, 2. R. Southwick 3. S. Haut 4. M. Core 5. R. Izac 6. M. Edmonds 7. J. Brady 1978 L