| Title: | "Synthesis and odor description of both enantiomers of methyl 4,5-didehydrojasmonate, a component of jasmin absolute" |
| Author(s): | Asamitsu Y; Nakamura Y; Ueda M; Kuwahara S; Kiyota H; |
| Address: | "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" |
| ISSN/ISBN: | 1612-1880 (Electronic) 1612-1872 (Linking) |
| Abstract: | "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" |
| Keywords: | Cyclopentanes/analysis/*chemical synthesis/*chemistry Esters/analysis/*chemical synthesis/*chemistry Humans Jasminum/*chemistry Lactams/chemistry Molecular Structure Odorants/*analysis Oxylipins Smell/*physiology Stereoisomerism; |
| Notes: | "MedlineAsamitsu, Yuko Nakamura, Yoko Ueda, Minoru Kuwahara, Shigefumi Kiyota, Hiromasa eng Switzerland 2006/12/29 Chem Biodivers. 2006 Jun; 3(6):654-9. doi: 10.1002/cbdv.200690068" |
