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

The Tetrahydroirones

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Photo by permission of M. Roudintska - Art & Parfum

(1R,3S, 6S)-(+)-Tetrahydroirone - Woody, powdery, ambergris

= (+)-4-[(1R,3S,6S)-2,2,3,6-tetramethylcyclohexyl]-butan-2-one

Ref: Christian Chapuis & Robert Brauchli, Preparation of Optically Active Flowery and Woody-Like Odorant Ketones via Corey-Chaykovsky Oxiranylation: Irones and Analogues , Helv.Chim.Acta 1993, 76: 2070-2088; Elisabetta Brenna, Claudio Fuganti and Stefano Serra, Enantioselective perception of chiral odorants, Tetrahedron: Asymmetry, 14, 1–42 (2003)

(1S,3R,6R)-(-)-Tetrahydroirone - Unpleasant

= (-)-4-[(1S,3R,6R)-2,2,3,6-tetramethylcyclohexyl]-butan-2-one

Ref: Christian Chapuis & Robert Brauchli, Preparation of Optically Active Flowery and Woody-Like Odorant Ketones via Corey-Chaykovsky Oxiranylation: Irones and Analogues , Helv.Chim.Acta 1993, 76: 2070-2088; 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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