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

The 1-(2',2',6'-trimethylcyclohexyloxy)-2-pentanols

(The Oxa-Norlimbanol®s)

 

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Photo by permission of M. Roudintska - Art & Parfum

(1'R,2S,6'S)-(+)-1-(2',2',6'-trimethylcyclohexyloxy)-2-pentanol - amber, costus, Limbanol®-type; dry, very powerful much more powerful than the three other possible optically active isomers. Its odour possesses a top note of the amber type which is particularly strong, accompanied by a woody note, less pronounced than in the other isomers. Its fragrance is also characterised by its dryness and an original costus note, which is lacking in the odour of the racemic mixture.

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® and Norimbanol® are trademarks of Firmenich SA

(1'S,2R,6'R)-(-)-1-(2',2',6'-trimethylcyclohexyloxy)-2-pentanol - woody, earthy, sesquiterpenes, lacks character; odoriferous notes of the woody type, but much less powerful than the (1'R,2S,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® and Norimbanol® are trademarks of Firmenich SA

(+)-(1'R,2R,6'S)-1-(2',2',6'-trimethyl-1'-cyclohexyloxy)-2-pentanol - woody, amber, lacks character

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® and Norimbanol® are trademarks of Firmenich SA

(-)-(1'S,2S,6'R)-1-(2',2',6'-trimethyl-1'-cyclohexyloxy)-2-pentanol - woody, pencil, without character

 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® and Norimbanol® are trademarks 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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