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

The 12-methyl-13-tetradecanolides

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Photo by permission of M. Roudintska - Art & Parfum

(12S,13R)-(-)-12-methyl-13-tetradecanolide - animalic cedar wood profile with camphoraceous aspects; devoid of musk notes

Ref: P. Kraft, W. Tochtermann, Ring Enlargement by Alkylated 3-Hydroxybutyrates: A Synthesis of (12S, 13R)-(-)-12-Methyl-13-tetradecanolide, Tetrahedron, 51, 10875- 10882 (1995); Georg Frater, Urs Muller, and Philip Kraft, Preparation and Olfactory Characterization of the Enantiomerically Pure Isomers of the Perfumery Synthetic Galaxolide, Helv. Chim. Acta, 82, 1656-1665 (1999)

(12R,13S)-(+)-12-methyl-13-tetradecanolide - strong woody odor with a pronounced musk character

Ref: B. Bollbuck, W. Tochtermann, Novel Chiral Building Blocks Derived from Baker´s Yeast Reduction Products: Synthesis and Odour of Mono- and Bicyclic Macrolides, Tetrahedron, 55, 7191-7208 (1999); Georg Frater, Urs Muller, and Philip Kraft, Preparation and Olfactory Characterization of the Enantiomerically Pure Isomers of the Perfumery Synthetic Galaxolide, Helv. Chim. Acta, 82, 1656-1665 (1999)

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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