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

The Androstadienones

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Photo by permission of M. Roudintska - Art & Parfum

(8R,9R,10S,13S,14R)-(-)-Androsta-4,16-dien-3-one - ODORLESS

= (8R,9R,10S,13S,14R)-1,7,8,9,10,11,12,13,14,15-decahydro-10,13-dimethyl-2H-cyclopenta[a]phenanthren-3(6H)-one

Ref: G. Ohloff, B.Maurer, B. Winter & W. Giersch, Structural and Configurational Dependence of the Sensory Process in Steroids, Helv. Chim. Acta, 66, 192-217 (1983); G. Ohloff, Scent & Fragrances, Springer-Verlag (1994), p. 27

(8S,9S,10R,13R,14S)-(+)-Androsta-4,16-dien-3-one - "very persistent odor of urine & sweat"

Threshold = 0.98 ppb

= (8S,9S,10R,13R,14S)-1,7,8,9,10,11,12,13,14,15-decahydro-10,13-dimethyl-2H-cyclopenta[a]phenanthren-3(6H)-one

Ref: G. Ohloff, B.Maurer, B. Winter & W. Giersch, Structural and Configurational Dependence of the Sensory Process in Steroids, Helv. Chim. Acta, 66, 192-217 (1983); G. Ohloff, Scent & Fragrances, Springer-Verlag (1994), p. 27; John E. Amoore, et. al., Chem. Senses Flavour, 2, 401-425 (1977)

 

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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