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

The 1-(2,2,3,6-Tetramethylcyclohexyloxy)-pentan-2-ols

The Oxa-Limbanol®s

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Photo by permission of M. Roudintska - Art & Parfum

(+)-(1'R,2S,3'S,6'S)-1-(2,2,3,6-Tetramethylcyclohexyloxy)-pentan-2-ol - amber, woody, dry, exceedingly powerful; possesses a fragrance which is much more intense and long-lasting than that of the other possible optically active isomers. Its extremely intense woody fragrance also has an amber-scented, dry, very natural character. Furthermore, it has been ascertained, unexpectedly and highly advantageously, that the smell of this compound is entirely distinguished from that of the corresponding racemate by the fact that it does not have an animal/perspiration note.

Ref: Christian Margot, Dana P. Simmonsb, Daniel Reichlinc and David Skuya, Amber-Woody Scent: Alcohols with Divergent Structure Present Common Olfactory Characteristics and Sharp Enantiomer Differentiation, Helvetica Chimica Acta, Vol. 87, 2662-2684 (2004); Christian Margot, Optically active, oxygenated, alicyclic compounds and their use as perfuming ingredients, United States Patent Application 20010031710 (October 18, 2001)

Limbanol® is a registered trademark of Firmenich SA

(-)-(1'S,2R,3'R,6'R)-1-(2,2,3,6-Tetramethylcyclohexyloxy)-pentan-2-ol - woody, cedar, very weak to odorless; much weaker than the (+)-(1'R,2S,3'S,6'S)-isomer.

Ref: Christian Margot, Dana P. Simmonsb, Daniel Reichlinc and David Skuya, Amber-Woody Scent: Alcohols with Divergent Structure Present Common Olfactory Characteristics and Sharp Enantiomer Differentiation, Helvetica Chimica Acta, Vol. 87, 2662-2684 (2004); Christian Margot, Optically active, oxygenated, alicyclic compounds and their use as perfuming ingredients, United States Patent Application 20010031710 (October 18, 2001)

Limbanol® is a registered trademark of Firmenich SA

(-)-(1'S,2S,3'R,6'R)-1-(2,2,3,6-Tetramethylcyclohexyloxy)-pentan-2-ol - woody, paper, slightly amber, weak; however, in admixture with the (+)-(1'R,2S,3'S,6'S)-isomer, this is distinguished from the corresponding racemate by a fragrance characterised by a more intense amber-scented top note which is less sweet and balsamic than that of the racemic mixture. This mixture is appreciated for its woody, amber-scented fragrance devoid of all animal/perspiration notes. Indeed, the woody, amber-scented fragrance of the mixture also has a much more amber-scented/fruity, almost floral character which is much less cedar/animal than the fragrance of the racemate, Moreover, the said mixture has organoleptic characteristics which are very different from those of the corresponding racemate. Generally speaking, the compounds of the invention in which the hydroxyl group has an S configuration have a more intense smell than the others.

Ref: Christian Margot, Dana P. Simmonsb, Daniel Reichlinc and David Skuya, Amber-Woody Scent: Alcohols with Divergent Structure Present Common Olfactory Characteristics and Sharp Enantiomer Differentiation, Helvetica Chimica Acta, Vol. 87, 2662-2684 (2004); Christian Margot, Optically active, oxygenated, alicyclic compounds and their use as perfuming ingredients, United States Patent Application 20010031710 (October 18, 2001)

Limbanol® is a registered trademark of Firmenich SA

(+)-(1'R,2R,3'S,6'S)-1-(2,2,3,6-Tetramethylcyclohexyloxy)-pentan-2-ol - woody, amber, somewhat powerful

Ref: Christian Margot, Dana P. Simmonsb, Daniel Reichlinc and David Skuya, Amber-Woody Scent: Alcohols with Divergent Structure Present Common Olfactory Characteristics and Sharp Enantiomer Differentiation, Helvetica Chimica Acta, Vol. 87, 2662-2684 (2004); Christian Margot, Optically active, oxygenated, alicyclic compounds and their use as perfuming ingredients, United States Patent Application 20010031710 (October 18, 2001)

Limbanol® 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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