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

The Dehydrogeosmins

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Photo by permission of M. Roudintska - Art & Parfum

(+)-(4S,4aS,8aS)-dehydrogeosmin - strong, camphoraceous, earthy-musty tonality which is reminiscent of freshly ploughed soil - the natural (+) stereoisomer exhibiting a fresher and stronger camphoraceous tonality than the (-) isomer.

Odor recognition threshold = 140 pg/liter in air

= (+)-(4S,4aS,8aS)-4,8a-dimethyl-1,3,4,5,8,8a-hexahydronaphthalen-4a(2H)-ol

Ref: Udo Huber, Wilhelm Boland, Wilfried A. König, Bärbel Gehrcke,S ynthesis and Absolute Configuration of the C12-Terpenoid Dehydrogeosmin from the Flower Scents of Rebutia marsoneri and Dolichothele sphaerica (Cactaceae); a new approach to bis-angularly substituted trans-decalins, Helvetica Chimica Acta, Volume 76, Issue 5, Date: 11 August 1993, Pages: 1949-1955; Ronald Bentley, The Nose as a Stereochemist. Enantiomers and Odor, Chemical Reviews, 2006, 106, 4099-4112

(-)-(4R,4aR,8aR)-dehydrogeosmin - similar odor to (+)-dehydrogeosmin, but not as fresh or camphoraceous

Odor recognition threshold = 10 pg/liter in air

= (-)-(4R,4aR,8aR)-4,8a-dimethyl-1,3,4,5,8,8a-hexahydronaphthalen-4a(2H)-ol

Ref: Ref: Udo Huber, Wilhelm Boland, Wilfried A. König, Bärbel Gehrcke,S ynthesis and Absolute Configuration of the C12-Terpenoid Dehydrogeosmin from the Flower Scents of Rebutia marsoneri and Dolichothele sphaerica (Cactaceae); a new approach to bis-angularly substituted trans-decalins, Helvetica Chimica Acta, Volume 76, Issue 5, Date: 11 August 1993, Pages: 1949-1955; Ronald Bentley, The Nose as a Stereochemist. Enantiomers and Odor, Chemical Reviews, 2006, 106, 4099-4112

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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