The Contribution of Sucrose Esters to Tobacco Smoke Composition

Sucrose esters, principally the 6-O-acetyl-2,3,4-tri-O-(3-methylvaleryl)-a-D-glucopyranosyl-b-D-fructofuran-oside isomer, isolated from the cuticular waxes of green T.I. 165 tobacco leaf, were evaluated as enhancers of 3-methylvaleric acid in the smoke of a tobacco deficient in this important flavor compound. Analyses of the products from semi-micro pyrolyses of sucrose and isolated sucrose esters, over a temperature range of 250°C - 850°C, showed that free sucrose produced 5-hydroxy-methylfurfural as the major component, whereas the ester isolate yielded 3-methylvaleric acid and lesser amounts of isomeric C₄ and C₅ aliphatic acids. Incorporation of sucrose ester isolate of T.I. 165 leaf into cigarettes prepared from flue-cured NC 2326 tobacco, the smoke of which is essentially devoid of 3-methylvaleric acid, resulted in a total particulate matter with enhanced levels of this compound. The data indicated that addition of approximately 2 mg of sucrose ester isolate per cigarette produced levels of 3-methylvaleric acid in the smoke of NC 2326 cigarettes that were comparable to levels observed in the smoke from cigarettes containing all T.I. 165 or blended Turkish tobacco.