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

The Allyl gamma-cyclogeranates

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Photo by permission of M. Roudintska - Art & Parfum

Allyl (R)-gamma-cyclogeranate - more green, less blackcurrant, less floral, weaker than (S)-enantiomer

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

The racemic ethyl gamma-cyclogeranate is described as: rosy, green, metallic, slightly allylic (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)

 

Allyl (S)-gamma-cyclogeranate - green, floral, blackcurrant, aromatic, fruity, pleasant

= allyl (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

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