Chirality & Odour Perception
John C. Leffingwell, Ph.D.

The Methyl 4,5-didehydrojasmonates

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Photo by permission of M. Roudintska - Art & Parfum

(+)-(3S,7R)-(-)-Z-Methyl 4,5-didehydrojasmonate - the natural (3S,7R)-enantiomer has a fresh natural, sweet floral fruity odor, reminiscent of Jasmin and Ylang Ylang flower, more intensive and tenacious than the non-natural form (contained <1.5% of the epi-form).

= (1R,2S)-Z-Methyl 4,5-didehydrojasmonate or methyl {(1S,5R)-4-oxo-5-[(2Z)-pent-2-enyl]cyclopent-2-en-1-yl}acetate=

Ref: Yuko Asamitsu, Yoko Nakamura, Minoru Ueda, Shigefumi Kuwahara, Hiromasa Kiyota, Synthesis and Odor Description of Both Enantiomers of Methyl 4,5-Didehydrojasmonate, a Component of Jasmin Absolute, Chemistry & Biodiversity, Volume 3, Issue 6, Date: June 2006, Pages: 654-659

(-)-(3R,7S)-(-)-Z-Methyl 4,5-didehydrojasmonate - a floral green odor with slight metallic green aspect, less intensive than the natural form.

= (1S,2R)-Z-Methyl 4,5-didehydrojasmonate or methyl {(1R,5S)-4-oxo-5-[(2Z)-pent-2-enyl]cyclopent-2-en-1-yl}acetate=

Ref: Yuko Asamitsu, Yoko Nakamura, Minoru Ueda, Shigefumi Kuwahara, Hiromasa Kiyota, Synthesis and Odor Description of Both Enantiomers of Methyl 4,5-Didehydrojasmonate, a Component of Jasmin Absolute, Chemistry & Biodiversity, Volume 3, Issue 6, Date: June 2006, Pages: 654-659

Cyclic Terpenoid Odorants

Bicyclic Terpenoid Odorants

Acyclic Terpenoid Odorants

Ionones, Irones, Damascones & Structurally Related Odorants

Acyclics (Alcohols, Esters, Acids, Aldehydes)

Lactones

Sesquiterpenoid Related Odorants

Steroid Urine Type Odorants

Sandalwood Type Odorants

Musk Odorants

Miscellaneous

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