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

13 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
Externally publishedYes

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Enantiomers
Odors
Cananga
Fragrances
Biological Products
methyl 4,5-didehydrojasmonate
Odorants
methyl jasmonate

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Biology
  • Molecular Medicine

Cite this

Synthesis and odor description of both enantiomers of methyl 4,5-didehydrojasmonate, a component of jasmin absolute. / Asamitsu, Yuko; Nakamura, Yoko; Ueda, Minoru; Kuwahara, Shigefumi; Kiyota, Hiromasa.

In: Chemistry and Biodiversity, Vol. 3, No. 6, 2006, p. 654-659.

Research output: Contribution to journalArticle

Asamitsu, Yuko ; Nakamura, Yoko ; Ueda, Minoru ; Kuwahara, Shigefumi ; Kiyota, Hiromasa. / Synthesis and odor description of both enantiomers of methyl 4,5-didehydrojasmonate, a component of jasmin absolute. In: Chemistry and Biodiversity. 2006 ; Vol. 3, No. 6. pp. 654-659.
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