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

The alpha-Vetivones

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Photo by permission of M. Roudintska - Art & Parfum

(4S,4aR)- (-)- alpha-vetivone - completely lacks the fruity character of (+)- alpha-vetivone (Ohloff);

On an odor rating scale: Dusty-woody, spicy, slightly fresh, green, sour, herbal (Haring, et. al.)

Odor Threshold (in water) = 6.0-15.0 ppm (10,500 ppb average value)

= (-)-(4S,4aR)-4,4a-dimethyl-6-(1-methylethylidene)-4,4a,5,6,7,8-hexahydronaphthalen-2(3H)-one

Ref: G. Ohloff, Scent & Fragrances, Springer-Verlag, (1994), p. 44; H.G. Haring, F. Rijkens & H. Boelens, J. Agric. Food Chem., 20, 1018-1021 (1972); Mans H. Boelens, Harrie Boelens & Leo J. van Gemert, Perfumer & Flavorist, Vol. 18, No. 6, 1-15, 1993

(4R,4aS)-(+)-alpha-vetivone - some grapefruit charachter in combination with its strong characteristic woody balsamic odor; also has been described as floral-waxy-woody (Ohloff);

On an odor rating scale: dusty-woody, fresh, green, sour, spicy, herbal, animal, erogenic, slightly fruity (Haring, et. al.)

Odor Threshold (in water) = 0.6-1.0 ppm (800 ppb average value)

= (+)-(4R,4aS)-4,4a-dimethyl-6-(1-methylethylidene)-4,4a,5,6,7,8-hexahydronaphthalen-2(3H)-one

(+)- and (-)-alpha-vetivone have been tasted in a soft drink base by several experienced flavor chemists. (+)-alpha-Vetivone was perceptible at 1.6 ppm and at that concentration is slightly reminiscent of grapefruit. It also has a strong woody flavor, not appreciated by flavor chemists. (-)-alpha-Vetivone, perceptible at approximately 8 ppm, is weaker than the (+)-form but has an even stronger woody note (Haring, et. al.).

Ref: G. Ohloff, Scent & Fragrances, Springer-Verlag, (1994), p. 44; G. Ohloff & W. Giersch, in Gustation & Olfaction, An International Symposium, Geneva, June 1970, Academic Press, London, p. 184-186; H.G. Haring, F. Rijkens & H. Boelens, J. Agric. Food Chem., 20, 1018-1021 (1972); Mans H. Boelens, Harrie Boelens & Leo J. van Gemert, Perfumer & Flavorist, Vol. 18, No. 6, 1-15, 1993

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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