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

The Oxo-Muscolides

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Photo by permission of M. Roudintska - Art & Parfum

(-)-(S)-Oxo-muscolide - possesses a weak musk note, without animalic character, and is dominated by an odour reminiscent of ironed linen.

= (-)-(14S)-14-methyl-12-oxo-15-pentadecanolide

Ref: B. Bollbuck, P. Kraft, W. Tochtermann, Nature-like Odorants by Stereoselective Ring Enlargement of Cyclohexanone and Cyclododecanone, Tetrahedron 1996, 52, 4581-4592; see also Elisabetta Brenna, Claudio Fuganti and Stefano Serra, Enantioselective perception of chiral odorants, Tetrahedron: Asymmetry, 14, 1–42 (2003)

(+)-(R)-Oxo-muscolide - slightly musky and sweet, but not erogenous-animalic.

= (+)-(14R)-14-methyl-12-oxo-15-pentadecanolide

Ref: B. Bollbuck, P. Kraft, W. Tochtermann, Nature-like Odorants by Stereoselective Ring Enlargement of Cyclohexanone and Cyclododecanone, Tetrahedron 1996, 52, 4581-4592; see also 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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