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

The Celery Ketones

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Photo by permission of M. Roudintska - Art & Parfum

(R)-Celery Ketone - Celery leaves, arnica, jasmone, slightly reminiscent of everlastings and fenugreek

Odor Threshold = 9.1-1 ng/L (air)

The enantiomers of celery ketone differ as strikingly in their olfactory properties as in the rare case of carvone. Only the stronger (R)-enantiomer (odor threshold 9.1-1 ng/L air) is responsible for the characteristic celery note of the racemate, whereas the (S)-enantiomer, which is five times weaker (odor threshold 45.5-1 ng/L air), has an aniseed-like liquorice smell with minty facets.

Ref: Jian Zhou, Vijay Wakchaure, Philip Kraft, and Benjamin List, Primary-Amine-Catalyzed Enantioselective Intramolecular Aldolizations, Angew. Chem. Int. Ed. 2008, 47, 7656 –7658.Angew. Chem. Int. Ed. 2008, 47, 7656 –7658

(S)-Celery Ketone - Herbaceous (liquorice, anisic and fennel), slightly woody, minty and pulegone-like

Odor threshold = 45.5-1 ng/L (air)

The enantiomers of celery ketone differ as strikingly in their olfactory properties as in the rare case of carvone. Only the stronger (R)-enantiomer (odor threshold 9.1-1 ng/L air) is responsible for the characteristic celery note of the racemate, whereas the (S)-enantiomer, which is five times weaker (odor threshold 45.5-1 ng/L air), has an aniseed-like liquorice smell with minty facets.

Ref: Jian Zhou, Vijay Wakchaure, Philip Kraft, and Benjamin List, Primary-Amine-Catalyzed Enantioselective Intramolecular Aldolizations, Angew. Chem. Int. Ed. 2008, 47, 7656 –7658.Angew. Chem. Int. Ed. 2008, 47, 7656 –7658

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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