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ID 54768
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Enzyme-catalyzed synthesis and odor evaluation of both enantiomers of perfume compounds
Author
Kiyota, Hiromasa Graduate School of Environmental and Life Science, Okayama University
Abstract
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.
Keywords
flavor and fragrance
enantiomers
synthesis
methyl jasmonate
lavandulol
irone
Note
総合論文 (Monograph)
Published Date
2017-02-01
Publication Title
Scientific Reports of the Faculty of Agriculture, Okayama University
Volume
volume106
Publisher
岡山大学農学部
Publisher Alternative
FACULTY OF AGRICULTURE OKAYAMA UNIVERSITY
Start Page
33
End Page
38
ISSN
2186-7755
Content Type
Departmental Bulletin Paper
language
日本語
File Version
publisher
Refereed
False
Eprints Journal Name
srfa