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

The 2-Heptyl-cyclopropanecarboxylic acids

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Photo by permission of M. Roudintska - Art & Parfum

(-)-(1R,2S)-2-heptylcyclopropanecarboxylic acid - The enantiomers of the cis isomer give odour notes that can be described as follows: woody, balsamic, incense-like, green, herbal, pith-like and waxy; In addition, mixtures of the enantiomers of the cis isomers of 2-heptylcyclopropyl-1-carboxylic acid have a balsamic, peel-like but not aldehydic flavour note. However, the non-natural (1R,2S) cis enantiomer displays a very much weaker odour than the naturally occurring (1S,2R) enantiomer.

Ref: Sabine Widder; Jan Looft; Armin Van Der Kolk; Tobias Vossing; Wilhelm Pickenhagen; Birgit Kohlenberg; 2-heptylcyclopropyl-1-carboxylic acid , United States Patent Application 20060128603 (June 15, 2006)

(+)-(1S,2R)-2-heptylcyclopropanecarboxylic acid - The enantiomers of the cis isomer give odour notes that can be described as follows: woody, balsamic, incense-like, green, herbal, pith-like and waxy; In addition, mixtures of the enantiomers of the cis isomers of 2-heptylcyclopropyl-1-carboxylic acid have a balsamic, peel-like but not aldehydic flavour note. However, the natural (1S,2R) cis enantiomer displays a very much stronger odour than the non-naturally occurring (1R,2S) enantiomer.

The odour threshold for the racemic mixture of cis-2-heptylcyclopropyl-1-carboxylic acid is 3 ppb in water and is thus extremely low.

Ref: Sabine Widder; Jan Looft; Armin Van Der Kolk; Tobias Vossing; Wilhelm Pickenhagen; Birgit Kohlenberg; 2-heptylcyclopropyl-1-carboxylic acid , United States Patent Application 20060128603 (June 15, 2006)

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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