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

The Limbanols® (3'-Methyl-norlimbanols)

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Photo by permission of M. Roudintska - Art & Parfum

(+)-(1'R,3'S,6'S)- Limbanol® = (+)-(1'R,3'S,6'S)-3'-methyl-norlimbanol - woody-amber odor of extraordinary intensity, together with a slight transpiration side note

= (+)-(1'R,3'S,6'S)-1-(2',2',3',6'-tetramethyl-1'-cyclohexyl)-3-hexanol

Note that the C-3 position is epimeric, so this actually is a mixture of (1'R,3S,3'S,6'S) & (1'R,3R,3'S,6'S) isomers

Ref: Schulte-Elte, et al., Optically active aliphatic alcohols and their use as perfuming ingredients, United States Patent 6,054,426, April 25, 2000

Limbanol is a trademark of Firmenich SA

(-)-(1'S,3'R,6'R)-Limbanol® = (-)-(1'S,3'R,6'R)-3'-methyl-norlimbanol - a much weaker odor, albeit of similar character to the (+)-(1'R,3'S,6'S)-isomer

= (-)-(1'S,3'R,6'R)-1-(2',2',3',6'-tetramethyl-1'-cyclohexyl)-3-hexanol

Note that the C-3 position is epimeric, so this actually is a mixture of (1'S,3S,3'R,6'R) & (1'S,3R,3'S,6'R) isomers

Ref: Schulte-Elte, et al., Optically active aliphatic alcohols and their use as perfuming ingredients, United States Patent 6,054,426, April 25, 2000

Limbanol is a 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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