酵素触媒反応を鍵とする光学活性な香気物質両鏡像体の合成と香気評価

Synthesis of both enantiomers of some perfume compounds, and their difference in aroma characteristics are described. Enantiomeric pairs of methyl jasmonate and its 4,5-didehydro congener, principal components of jasmin absolute, were prepared from the corresponding commercially available racemates using lipase-catalyzed optical resolution. The E-value for the reaction is as high as 370. The nature-identical isomers produced superior aroma activity relative to unnatural ones. Racemic lavandulol from a commercial source, was also resolved using several enzymatic transesterifications followed by hydrolysis with PPL. Odor evaluation revealed that the nature-identical isomer should play a key role in lavender oil. Cis-α-irone and cis-γ-irone, used as important violet components for perfumery, were synthesized in optically active forms through fractional crystallization of the diastereomeric salts with α-phenethylamine. The nature-identical irones also had better floral characteristics like ionone.

総合論文 (Monograph)