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

The gamma-Damascones

 You must have Java installed to view the molecular visualization on this page
Photo by permission of M. Roudintska - Art & Parfum

(R)-gamma-damascone - Liquorice, damascone-like, camphoraceous, inferior to the (S)-enantiomer

Also known as (2E)-1-[(1R)-2,2-dimethyl-6-methylenecyclohexyl]but-2-en-1-one

Ref: Charles Fehr & Jose Galindo, Syntheses of the Enantiomers of gamma-Cyclogeranic Acid, gamma-Cyclocitral, and gamma-Damascone: Enantioselective Protonation of Enolates, Helv.Chim.Acta 1995, 78: 539-552; Elisabetta Brenna, Claudio Fuganti and Stefano Serra, Enantioselective perception of chiral odorants, Tetrahedron: Asymmetry, 14, 1–42 (2003)

(S)-gamma-damascone - Nice damascone character, camphoraceous

Also known as (2E)-1-[(1S)-2,2-dimethyl-6-methylenecyclohexyl]but-2-en-1-one

Ref: Charles Fehr & Jose Galindo, Syntheses of the Enantiomers of gamma-Cyclogeranic Acid, gamma-Cyclocitral, and gamma-Damascone: Enantioselective Protonation of Enolates, Helv.Chim.Acta 1995, 78: 539-552; Elisabetta Brenna, Claudio Fuganti and Stefano Serra, Enantioselective perception of chiral odorants, Tetrahedron: Asymmetry, 14, 1–42 (2003)

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

HOME

Copyright 2001 - Leffingwell & Associates