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

The 4-mercapto-2-octanones

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Photo by permission of M. Roudintska - Art & Parfum

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(4R)-4-mercapto-2-octanone - more unpleasant (catty, sulfury) descriptions for the (R)-enantiomer (by GC-O)

Odor Threshold = 0.09 ng/L air

= (4R)-4-sulfanyloctan-2-one

Ref: M. Wakabayashi, H. Wakabayashi, S. Nörenberg, B. Reichardt, K. Kubota, K.-H. Engel, Analytical and Sensory Characterization of Chiral 4-Mercapto-2-alkanones, 4-Acetylthio-2-alkanones, and the Corresponding Alcohols, ACS Symposium Series, Vol. 1098, Recent Advances in the Analysis of Food and Flavors, Chapter 3, pp 27–39, 2012

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(4S)-4-mercapto-2-octanone - more fruity-pleasant (grapefruit, blackcurrant) notes for the (S)-enantiomer (by GC-O)

Odor Threshold = 0.04 ng/L air

= (4S)-4-sulfanyloctan-2-one

Ref: M. Wakabayashi, H. Wakabayashi, S. Nörenberg, B. Reichardt, K. Kubota, K.-H. Engel, Analytical and Sensory Characterization of Chiral 4-Mercapto-2-alkanones, 4-Acetylthio-2-alkanones, and the Corresponding Alcohols, ACS Symposium Series, Vol. 1098, Recent Advances in the Analysis of Food and Flavors, Chapter 3, pp 27–39, 2012

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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