PYROLYSIS OF CHERRY RED TOBACCO AND 1-DEOXY-1-[(S)-2-(3-PYRIDYL)-1-PYRROLIDINYL]-BETA-D-FRUCTOSE (PYRANOSE AND FURANOSE ISOMERS) AMADORI PRODUCTS OF CHERRY RED TOBACCO

摘要

Nornicotine (NN) reacted with glucose and malic acid as a catalyst in dry methanol produced two NN Amadori rearrangement isomers (NDF). 1-Deoxy-1-[(S)-2-(3-pyridyl)-1-pyrrolidinyl]-beta-D-(fructopyranose) was the major isomer and -(fructofuranose) the minor isomer. Pyrolysis of NDF at 500 degrees C produced nicotine, NN, myosmine, pyridine, beta-picoline, 3-vinylpyridine, substituted NN, and compounds that produced pleasant and sweet aromas. Eleven percent of the NN content from ''cherry red'' (CR) tobacco in this study was in NDF form. CR tobacco pyrolyzed at 500 degrees C produced 10 of the same pyrolytic products as the NDF isomers. This suggests that NDF in CR tobacco possibly contributes the same pyrolytic products as the synthetic NDF. Pyrazines, lactones, furan derivatives, and short-chain carboxylic acids were also produced from pyrolysis of CR tobacco.