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

The Ebanols® [3-methyl-5-[2,2,3-trimethylcyclopent-3-en-1-yl]pent-4-en-2-ols]

(Sandalwood odorants)

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Photo by permission of M. Roudintska - Art & Parfum

(1R,2'R,3'S)-Ebanol - weak, no sandalwood odor relevance

= (2R,3S,4E)-3-methyl-5-[(1R)-2,2,3-trimethylcyclopent-3-en-1-yl]pent-4-en-2-ol

Ref: Bajgrowicz, Jerzy A., Frater, Georg, Optical isomers of derivatives of campholenic aldehyde, European Patent Application No. 0841318, May 13, 1998

Ebanol® is a trademark of Givaudan SA

(1S,2'S,3'R)-Ebanol - Powerful sandalwood, more than 100X more powerful than its enantiomer (based on relative GC sniff threshold) and more than 3X stronger than (1R,2'S,3'R)-Ebanol

= (2S,3R,4E)-3-methyl-5-[(1S)-2,2,3-trimethylcyclopent-3-en-1-yl]pent-4-en-2-ol

Ref: Bajgrowicz, Jerzy A., Frater, Georg, Optical isomers of derivatives of campholenic aldehyde, European Patent Application No. 0841318, May 13, 1998

Ebanol® is a trademark of Givaudan SA

(1R,2'S,3'S)-Ebanol - Slight sandalwood relevance, both enantiomers weak

= (2S,3S,4E)-3-methyl-5-[(1R)-2,2,3-trimethylcyclopent-3-en-1-yl]pent-4-en-2-ol

Ref: Bajgrowicz, Jerzy A., Frater, Georg, Optical isomers of derivatives of campholenic aldehyde, European Patent Application No. 0841318, May 13, 1998

Ebanol® is a trademark of Givaudan SA

(1S,2'R,3'R)-Ebanol - No sandalwood relevance, both enantiomers weak

= (2R,3R,4E)-3-methyl-5-[(1S)-2,2,3-trimethylcyclopent-3-en-1-yl]pent-4-en-2-ol

Ref: Bajgrowicz, Jerzy A., Frater, Georg, Optical isomers of derivatives of campholenic aldehyde, European Patent Application No. 0841318, May 13, 1998

Ebanol® is a trademark of Givaudan SA

(1R,2'S,3'R)-Ebanol - Powerful sandalwood, more than 33X more powerful than its enantiomer and more than 3X weaker than (1S,2'S,3'R)-Ebanol

= (2S,3R,4E)-3-methyl-5-[(1R)-2,2,3-trimethylcyclopent-3-en-1-yl]pent-4-en-2-ol

Ref: Bajgrowicz, Jerzy A., Frater, Georg, Optical isomers of derivatives of campholenic aldehyde, European Patent Application No. 0841318, May 13, 1998

Ebanol® is a trademark of Givaudan SA

(1S,2'R,3'S)-Ebanol - no sandalwood relevance

= (2R,3S,4E)-3-methyl-5-[(1S)-2,2,3-trimethylcyclopent-3-en-1-yl]pent-4-en-2-ol

Ref: Bajgrowicz, Jerzy A., Frater, Georg, Optical isomers of derivatives of campholenic aldehyde, European Patent Application No. 0841318, May 13, 1998

Ebanol® is a trademark of Givaudan SA

(1R,2'R,3'R)-Ebanol - no sandalwood relevance

= (2R,3R,4E)-3-methyl-5-[(1R)-2,2,3-trimethylcyclopent-3-en-1-yl]pent-4-en-2-ol

Ref: Bajgrowicz, Jerzy A., Frater, Georg, Optical isomers of derivatives of campholenic aldehyde, European Patent Application No. 0841318, May 13, 1998

Ebanol® is a trademark of Givaudan SA

(1S,2'S,3'S)-Ebanol - no sandalwood relevance

= (2S,3S,4E)-3-methyl-5-[(1S)-2,2,3-trimethylcyclopent-3-en-1-yl]pent-4-en-2-ol

Ref: Bajgrowicz, Jerzy A., Frater, Georg, Optical isomers of derivatives of campholenic aldehyde, European Patent Application No. 0841318, May 13, 1998

Ebanol® is a trademark of Givaudan 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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