Synthesis and odor description of both enantiomers of methyl 4,5-didehydrojasmonate, a component of jasmin absolute

Yuko Asamitsu, Yoko Nakamura, Minoru Ueda, Shigefumi Kuwahara, Hiromasa Kiyota

Research output: Contribution to journalArticle

14 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)654-659
Number of pages6
JournalChemistry and Biodiversity
Volume3
Issue number6
DOIs
Publication statusPublished - 2006

ASJC Scopus subject areas

  • Bioengineering
  • Biochemistry
  • Chemistry(all)
  • Molecular Medicine
  • Molecular Biology

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