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

The Vulcanonitriles

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Photo by permission of M. Roudintska - Art & Parfum

(R,R)-(+)-Vulcanonitrile - similar, but less musky and woody than the (-)-(6S,7S) enantiomer

It has been observed that 5,6,7,8-tetrahydro-3,5,5,6,7,8,8-heptamethyl- 2-naphthalenecarbonitrile possesses an earthy and musky odor, the bottom note of which is provided with a humus-like and earthy character which strongly resembles the odor of its aldehydic analogue Vulcanolide®. Although the note of the racemic nitrile is similar to that developed by its enantiomers (-)-(6S,7S) and (+)-(6R,7R), the odor character of the latter is distinct from that of the racemate insofar as (-)-(6S,7S)-5,6,7,8-tetrahydro-3,5,5,6,7,8,8-heptamethyl-2-naphthalenecarbonitrile possesses a stronger and woodier note than its (+)-(6R,7R) enantiomer.

= (+)-(6R,7R)-3,5,5,6,7,8,8-heptamethyl-5,6,7,8-tetrahydronaphthalene-2-carbonitrile

Ref: Charles Fehr, Franqois Delay, Pierre-Main Blanc, Nathalie Chaptal-Gradoz, United States Patent No. 5,521,151, May 28, 1996; EP 664286 A1, July 26, 1995.

Vulcanonitrile is a trivial name based on analogy with Vulcanolide® (which is a registered trademark of Firmenich SA)

(S,S)-(-)-Vulcanonitrile - stronger earthy, musky and woodier note than its (+)-(6R,7R) enantiomer.

It has been observed that 5,6,7,8-tetrahydro-3,5,5,6,7,8,8-heptamethyl- 2-naphthalenecarbonitrile possesses an earthy and musky odor, the bottom note of which is provided with a humus-like and earthy character which strongly resembles the odor of its aldehydic analogue Vulcanolide®. Although the note of the racemic nitrile is similar to that developed by its enantiomers (-)-(6S,7S) and (+)-(6R,7R), the odor character of the latter is distinct from that of the racemate insofar as (-)-(6S,7S)-5,6,7,8-tetrahydro-3,5,5,6,7,8,8-heptamethyl-2-naphthalenecarbonitrile possesses a stronger and woodier note than its (+)-(6R,7R) enantiomer.

= (-)-(6S,7S)-3,5,5,6,7,8,8-heptamethyl-5,6,7,8-tetrahydronaphthalene-2-carbonitrile

Ref: Charles Fehr, Franqois Delay, Pierre-Main Blanc, Nathalie Chaptal-Gradoz, United States Patent No. 5,521,151, May 28, 1996; EP 664286 A1, July 26, 1995.

Vulcanonitrile is a trivial name based on analogy with Vulcanolide® (which is a registered trademark of Firmenich SA)

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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