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, Delta(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 (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.
Asamitsu
Yuko
Y
Department of Applied Bioorganic Chemistry, Division of Bioscience & Biotechnology for Future Bioindustry, Graduate School of Agricultural Science, Tohoku University, 1-1 Tsutsumidori-Amamiya, Aoba-ku, Sendai 981-8555, Japan.
Nakamura
Yoko
Y
Ueda
Minoru
M
Kuwahara
Shigefumi
S
Kiyota
Hiromasa
H
D003517:Cyclopentanes / Q000032:analysis / Q000138:chemical synthesis* / Q000737:chemistry*; D004952:Esters / Q000032:analysis / Q000138:chemical synthesis* / Q000737:chemistry*; D006801:Humans; D031660:Jasminum / Q000737:chemistry*; D007769:Lactams / Q000737:chemistry; D015394:Molecular Structure; D009812:Odorants / Q000032:analysis*; D054883:Oxylipins; D012903:Smell / Q000502:physiology*; D013237:Stereoisomerism
D003517:Cyclopentanes; D004952:Esters; D007769:Lactams; D054883:Oxylipins; C519297:methyl 4,5-didehydrojasmonate