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

The trans-Pinocarvyl propionates

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Photo by permission of M. Roudintska - Art & Parfum

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(1S,3R,5S)-(+)-trans-Pinocarvyl propionate - Probability levels of significant differentiation between the enantiomer pairs - >99.9% with 32 untrained panelists; >99.9% with 19 expert panelists; overall >99.9% (all 51 panelists).

Although no comments on the odor of the enantiomers was provided in Theimer's paper, Mans Boelens indicates that Pinocarvyl propionate is herbal, slightly fruity; somewhat minty & camphoraceous while Chattopadhyay indicates it has a fresh, fruity, pine, woody odor

= (1S,3R,5S)-6,6-dimethyl-2-methylenebicyclo[3.1.1]hept-3-yl propionate

Ref: E.T. Theimer and Mina R. McDaniel, Odor and optical activity, J. Soc. Cosmet. Chem. 22, 5-26 (1971); Mans Boelens, PMP 2001 - Database of Perfumery Materials & Performance, Leffingwell & Associates, Canton, GA (USA); P. K. Chattopadhyay, Herbal Cosmetics & Ayurvedic Medicines (EOU), National Institute of Industrial Research, India, 1998, p. 257

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(1R,3S,5R)-(-)-trans-Pinocarvyl propionate - Probability levels of significant differentiation between the enantiomer pairs - >99.9% with 32 untrained panelists; >99.9% with 19 expert panelists; overall >99.9% (all 51 panelists).

Although no comments on the odor of the enantiomers was provided in Theimer's paper, Mans Boelens indicates that Pinocarvyl propionate is herbal, slightly fruity; somewhat minty & camphoraceous while Chattopadhyay indicates it has a fresh, fruity, pine, woody odor

= (1R,3S,5R)-6,6-dimethyl-2-methylenebicyclo[3.1.1]hept-3-yl propionate

Ref: E.T. Theimer and Mina R. McDaniel, Odor and optical activity, J. Soc. Cosmet. Chem. 22, 5-26 (1971); Mans Boelens, PMP 2001 - Database of Perfumery Materials & Performance, Leffingwell & Associates, Canton, GA (USA); P. K. Chattopadhyay, Herbal Cosmetics & Ayurvedic Medicines (EOU), National Institute of Industrial Research, India, 1998, p. 257

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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