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

The Vulcanolides®

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Photo by permission of M. Roudintska - Art & Parfum

(R,R)-(+)-Vulcanolide - this enantiomer develops a fragrance of a less earthy character, with a woody side and the strength of which is clearly inferior to the (S,S)-enantiomer.

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

Ref: Charles Fehr, Nathalie Chaptal-Gradoz, Syntheses of the Enantiomers of Vulcanolide®, Volume 85, Issue 2, Date: February 2002, Pages: 533-543; Charles Fehr, Nathalie Chaptal-Gradoz, José Galindo, Synthesis of (-)-Vulcanolide by Enantioselective Protonation, Chemistry - A European Journal, Volume 8, Issue 4, Date: February 15, 2002, Pages: 853-858; 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.

Vulcanolide ® is a registered trademark of Firmenich SA

(S,S)-(-)-Vulcanolide - this enantiomer possesses the best developed odor properties. Its musky, markedly earthy, slightly amber character is particularly powerful.

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

Ref: Charles Fehr, Nathalie Chaptal-Gradoz, Syntheses of the Enantiomers of Vulcanolide®, Volume 85, Issue 2, Date: February 2002, Pages: 533-543; Charles Fehr, Nathalie Chaptal-Gradoz, José Galindo, Synthesis of (-)-Vulcanolide by Enantioselective Protonation, Chemistry - A European Journal, Volume 8, Issue 4, Date: February 15, 2002, Pages: 853-858; 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.

Vulcanolide ® 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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