Characterization of thermolysis products of cuticular wax compounds of green tobacco leaf

• Published in: Journal of analytical and applied pyrolysis 1989-12, Vol.17 (1), p.25-35
• Main Authors: Schlotzhauer, William S., Arrendale, R.F., Severson, R.F., Chortyk, O.T.
• Format: Article
• Language: English
• Subjects: Gas chromatography; mass spectrometry; pyrolysis; tobacco; waxes, cuticular
• ISSN: 0165-2370; 1873-250X
• DOI: 10.1016/0165-2370(89)85003-X

A study was undertaken to determine the pyrolysis products of leaf surface constituents of tobacco that may contribute to the flavor and aroma of smoke. Compounds previously identified in cuticular waxes of green tobacco (diterpenes, aliphatic alcohols, wax esters, hydrocarbons) were subjected to semimicro pyrolyses within a range of temperatures (200–800°C) that are encountered during smoking of tobacco products. Recovered products were characterized by gas chromatography/mass spectrometry. During thermolysis, the aliphatic hydrocarbons were found to undergo thermal desorption. The C 22 alcohol, docosanol, exhibited thermolytic behavior analogous to that of the paraffinic hydrocarbons, mainly distilling and producing only minor amounts of the corresponding 1-alkene. The duvane diterpenes, the α- and β-duvatrienediols, yielded four major products, with mass spectrometric characteristics of C 20 monols or C 20-seco cembranoids. The labdane diterpene, cis-abienol, thermally isomerized to the trans-neo-abienol isomer. The thermal degradation of wax esters increased with chain length, producing the corresponding alkene, alcohol, and acid products.