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

The Isophoryl propionates
(3,5,5-trimethylcyclohex-2-enyl propionates)

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Photo by permission of M. Roudintska - Art & Parfum

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(R)-Isophoryl propionate - Odor description: a forest berry note

= (1R)-3,5,5-trimethylcyclohex-2-en-1-yl propionate

Ref: K. Wiñska and C. Wawrzeñczyk, Synthesis of Chiral Odoriferous Oxy-derivatives of 1,5,5-Trimethylcyclohexene, Polish J. Chem., 81, 1887–1897 (2007) as reviewed in Elisabetta Brenna, Claudio Fuganti, Francesco G. Gatti, and Stefano Serra, Biocatalytic Methods for the Synthesis of Enantioenriched Odor Active Compounds, Chem. Rev., Article ASAP, DOI: 10.1021/cr100289r, Publication Date (Web): May 20, 2011

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(S)-Isophoryl propionate - Odor description: similar to the racemate, fruity with freshly collected blackcurrant note

= (1S)-3,5,5-trimethylcyclohex-2-en-1-yl propionate

Ref: K. Wiñska and C. Wawrzeñczyk, Synthesis of Chiral Odoriferous Oxy-derivatives of 1,5,5-Trimethylcyclohexene, Polish J. Chem., 81, 1887–1897 (2007) as reviewed in Elisabetta Brenna, Claudio Fuganti, Francesco G. Gatti, and Stefano Serra, Biocatalytic Methods for the Synthesis of Enantioenriched Odor Active Compounds, Chem. Rev., Article ASAP, DOI: 10.1021/cr100289r, Publication Date (Web): May 20, 2011

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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