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

The 10-Acetyl-9,10-dimethylbicyclo[6.4.0]dodec-1(8)-enes

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Photo by permission of M. Roudintska - Art & Parfum

(-)-(9R,10S)-10-Acetyl-9,10-dimethylbicyclo[6.4.0]dodec-1(8)-ene - it emanates a strong woody-ambery odor reminiscent of Iso E Super, Georgywood and cedarwood, and has an odor threshold of 0.19 ng/L air which is about 100 times stronger than its enantiomer.

Odor Threshold = 0.19 ng/L air

= (-)-1-[(1R,2S)-1,2-dimethyl-1,2,3,4,5,6,7,8,9,10-decahydrobenzo[8]annulen-2-yl]ethanone

Ref: Philip Kraft, Sofia Gallo, (-)-(9R,10S)-10-Acetyl-9,10-dimethylbicyclo[6.4.0]dodec-1(8)-ene: Optical Resolution, Catalyst Systems, Derivatives and Olfactory Properties, Synthesis 2004: 381-388.

(+)-(9R,10S)-10-Acetyl-9,10-dimethylbicyclo[6.4.0]dodec-1(8)-ene - possesses a similar odor character to the (-)-(9R,10S)-enantiomer but is about 100 times weaker.

Odor Threshold = ca. 20 ng/L air

= (+)-1-[(1S,2R)-1,2-dimethyl-1,2,3,4,5,6,7,8,9,10-decahydrobenzo[8]annulen-2-yl]ethanone

Ref: Philip Kraft, Sofia Gallo, (-)-(9R,10S)-10-Acetyl-9,10-dimethylbicyclo[6.4.0]dodec-1(8)-ene: Optical Resolution, Catalyst Systems, Derivatives and Olfactory Properties, Synthesis 2004: 381-388.

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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