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

The Nootkatones

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Photo by permission of M. Roudintska - Art & Parfum

(-)-(4S,4aR,6S)-nootkatone - weak woody (vetiver note); no grapefruit character; virtually no taste;

On an odor rating scale: Dusty-woody, spicy, slightly fresh, green, sour, herbal

= (-)-(4S,4aR,6S)-6-Isopropenyl-4,4a-dimethyl-4,4a,5,6,7,8-hexahydro-3H-naphthalen-2-one

Odor Threshold = 600000 ppb (Average of values)

Ref: H.G. Haring, F. Rijkens & H. Boelens, Olfactory Studies on Enantiomeric Eremophilane Sesquiterpenoids, J. Agric. Food Chem., 20, 1018 (1972); Mans H. Boelens, Harrie Boelens & Leo J. van Gemert, Perfumer & Flavorist, Vol. 18, No. 6, 1-15, 1993

(+)-(4R,4aS,6R)-nootkatone - strong grapefruit odor, bitter in taste

On an odor rating scale: Strongly fresh, green, sour; dusty-woody; animal-erogenic, slightly herbal, fruity

= (+)- (4R,4aS,6R)-6-Isopropenyl-4,4a-dimethyl-4,4a,5,6,7,8-hexahydro-3H-naphthalen-2-one

Odor Threshold = 800 ppb (Average of values)

(+)- and (-)-nootkatone have been tasted in a soft drink base by several experienced flavor chemists. (+)-Nootkatone was perceptible at a concentration of approximately 0.3 ppm and still had the flavor character of grapefruit. (-)-Nootkatone was perceptible at 40 ppm (much lower than the odor threshold value for aqueous solutions) and at that concentration tasted bitter and sour without any flavor impression.

Ref: H.G. Haring, F. Rijkens & H. Boelens, Olfactory Studies on Enantiomeric Eremophilane Sesquiterpenoids, J. Agric. Food Chem., 20, 1018 (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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