Synthesis and Odor Description of Both Enantiomers of Methyl 4,5-Didehydrojasmonate, a Component of Jasmin Absolute

Synthesis of both enantiomers of methyl 4,5‐didehydrojasmonate (1, Δ4,5‐MJA; >99.8% ee), a constituent of jasmin absolute, established the absolute configuration of the natural product, and their odor quality was evaluated. The fragrance of the natural (3S,7R)‐enantiomer (a fresh natural, sweet f...

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Bibliographic Details
Published in:Chemistry & biodiversity 2006-06, Vol.3 (6), p.654-659
Main Authors: Asamitsu, Yuko, Nakamura, Yoko, Ueda, Minoru, Kuwahara, Shigefumi, Kiyota, Hiromasa
Format: Article
Language:English
Subjects:
5-didehydro
Cyclopentanes - analysis
Cyclopentanes - chemical synthesis
Cyclopentanes - chemistry
Esters - analysis
Esters - chemical synthesis
Esters - chemistry
Flavors
Fragrances
Humans
Jasmin absolute
Jasminum - chemistry
Jasmonate
Jasmonate, methyl 4,5‐didehydro
Lactams - chemistry
methyl 4
Molecular Structure
Odor description
Odorants - analysis
Oxylipins
Smell - physiology
Stereoisomerism
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Summary:Synthesis of both enantiomers of methyl 4,5‐didehydrojasmonate (1, Δ4,5‐MJA; >99.8% ee), a constituent of jasmin absolute, established the absolute configuration of the natural product, and their odor quality was evaluated. The fragrance of the natural (3S,7R)‐enantiomer (a fresh natural, sweet floral fruity odor, reminiscent of Jasmin and Ylang Ylang flower, more intensive and tenacious) was superior to that of the unnatural (3R,7S)‐enantiomer (a floral green odor with slight metallic green aspect, less intensive than the natural form) and the racemate (green‐floral note, having weak and less volume than methyl jasmonate). Odor difference between natural and unnatural enantiomers of methyl jasmonate (2) is also reported.
ISSN:1612-1872
1612-1880
DOI:10.1002/cbdv.200690068