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

The Androstenols

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Photo by permission of M. Roudintska - Art & Parfum

ent-(-)-5-alpha-androst-16-en-3-alpha-ol - Much weaker with a detection threshold level about six orders of magnitude higher than (+)-5-alpha-androst-16-en-3-alpha-ol

= (3S,5R,8S,9R,10R,13S,14R)-androst-16-en-3-ol

= (3S,5R,8S,9R,10R,13S,14R)-2,3,4,5,6,7,8,9,10,11,12,13,14,15-tetradecahydro-10,13-dimethyl-1H-cyclopenta[a]phenanthren-3-ol

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

(+)-5-alpha-androst-16-en-3-alpha-ol - Animalic, musk-like odor with a strong (fine) sandalwood tonality

Threshold: 0.02 ppb (in air)

= (3R,5S,8R,9S,10S,13R,14S)-androst-16-en-3-ol

= (3R,5S,8R,9S,10S,13R,14S)-2,3,4,5,6,7,8,9,10,11,12,13,14,15-tetradecahydro-10,13-dimethyl-1H-cyclopenta[a]phenanthren-3-ol

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; Bajgrowicz, J.A. & G. Frater (2000), Chiral recognition of sandalwood odorants, Enantiomer, 5, 225-234

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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