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TSRC, Tob. Sci. Res. Conf., 2010, 64, abstr. 68

Glycosides - flavour enhancers in smoke

PALANI N.; VINUTHA S.; DINESH T.K.; SINGH M.K.; MUKHERJEE S.; DHALEWADIKAR S.V.
ITC R&D Centre, Peenya, Bangalore, India

Glycosides in food materials have been extensively studied in recent years, and interest has been focused on their role as flavor precursors. Glycosidic components of tobacco leaves could also contribute to generating aroma and taste in the curing and aging process of tobacco. Sugars when combined with alcohols, phenols, polyphenols and sterols to form glycosides which are non volatile flavor precursors present in tobacco. These on pyrolyses release aglycones (flavor compounds) which enhances the smoke flavor. Menthol, because of its inherent mint flavour and refreshing feeling, has been used as additives to medicines, tobaccos, foodstuffs etc. The volatility limited its wider application in the high temperature processing and it is overcome by converting menthol to its glycoside which is non volatile and stable. Menthyl glycoside was synthesized using Menthol and readily available triacetyl glucal.

The above menthyl glycoside was added into a cigarette and cooling effect due to menthol release was felt while smoking. We also synthesized other glycosides using viz Phenylethylalcohol, Citronellol and benzyl alcohol. These glycosides were added in the cigarette and they enhanced the smoke flavour. All these molecules are well characterized 1HNMR and 13C NMR. These glycosides gave a positive smoke flavor in the smoke.