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Synthesis and Odor Description of Both Enantiomers of Methyl 4,5‐Didehydrojasmonate, a Component of Jasmin Absolute
Author(s) -
Asamitsu Yuko,
Nakamura Yoko,
Ueda Minoru,
Kuwahara Shigefumi,
Kiyota Hiromasa
Publication year - 2006
Publication title -
chemistry and biodiversity
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.427
H-Index - 70
eISSN - 1612-1880
pISSN - 1612-1872
DOI - 10.1002/cbdv.200690068
Subject(s) - odor , enantiomer , chemistry , methyl jasmonate , natural product , absolute (philosophy) , stereochemistry , organic chemistry , biochemistry , philosophy , gene , epistemology
Synthesis of both enantiomers of methyl 4,5‐didehydrojasmonate ( 1 , Δ 4,5 ‐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 (3 S ,7 R )‐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 (3 R ,7 S )‐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.