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

The trans-Aerangis lactones

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Photo by permission of M. Roudintska - Art & Parfum

(4S,5R)-trans-aerangis lactone - reminiscent of delta-decalactone and cocos, with similar intensity to the cis-(4R,5R)-enantiomer and higher than the trans-(4R,5S)-enantiomer

Odor threshold = 50 ng

Also known as (4S,5R)-trans-4-methyl-5-decanolide or (5S,6R)-trans-6-pentyl-5-methyltetrahydropyran-2-one

Ref: Bartschat, D., Lehmann, D., Dietrich, A., Mosandl, A., Kaiser, R. (1995). Chiral compounds of essential oils XIX: 4-Methyl-5-decanolide: Chirospecific analysis, structure and properties of the stereoisomers. Phytochem. Anal., 6, 130-134; Elisabetta Brenna, Claudio Fuganti and Stefano Serra, "Enantioselective perception of chiral odorants", Tetrahedron Asymmetry, 14 (1), 1–42, 2003

(4R,5S)-trans-aerangis lactone - showed slightly lactonic fragrance, with the lowest fragrance intensity of all the stereoisomers

Odor threshold = 100 ng.

Also known as (4R,5S)-trans-4-methyl-5-decanolide or (5R,6S)-trans-6-pentyl-5-methyltetrahydropyran-2-one

Ref: Bartschat, D., Lehmann, D., Dietrich, A., Mosandl, A., Kaiser, R. (1995). Chiral compounds of essential oils XIX: 4-Methyl-5-decanolide: Chirospecific analysis, structure and properties of the stereoisomers. Phytochem. Anal., 6, 130-134; Elisabetta Brenna, Claudio Fuganti and Stefano Serra, "Enantioselective perception of chiral odorants", Tetrahedron Asymmetry, 14 (1), 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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