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

The Ethyl gamma-cyclogeranates

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

Ethyl (R)-gamma-cyclogeranate - less fruity, aromatic, rosemary, less powerful than the (S)-enantiomer

= ethyl (1R)-2,2-dimethyl-6-methylenecyclohexanecarboxylate

The racemic ethyl gamma-cyclogeranate is described as: develops a floral, rosy odor, with a less pronounced damascone character than that of its methyl ester homologue, but more metallic than the latter. On the other hand, the thujonic-absinthe side of the note is much more pronounced in the ethyl ester odor. When compared to its methyl alpha-cyclogeranate isomer, the racemic ethyl gamma-cyclogeranate is shown to possesses a more camphoraceous, fruity, damascone-like and elegant odor note than that methyl alpha-cyclogeranate (US Patent No. 5,015,625).

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); Charles Fehr & Jose Galindo, Alicyclic esters and their use as perfuming ingredients, United States Patent 5,015,625 (May 14, 1991)

 

Ethyl (S)-gamma-cyclogeranate - aromatic, fruity, damascone-like

= ethyl (1S)-2,2-dimethyl-6-methylenecyclohexanecarboxylate

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