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

The Isophorols (3,5,5-trimethylcyclohex-2-enols)

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Photo by permission of M. Roudintska - Art & Parfum

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(R)-Isophorol - Odor description: The Racemate and the (R)-, and (S)-enantiomers showed very similar odors, with terpenic, camphor, and borneol notes

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

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)-Isophorol - Odor description: The Racemate and the (R)-, and (S)-enantiomers showed very similar odors, with terpenic, camphor, and borneol notes

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

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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