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

The 4-[2,2,3-trimethylcyclopent-3-en-1-yl]but-3-en-2-ones

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Photo by permission of M. Roudintska - Art & Parfum

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(-)-(3E/Z)-4-((1'R)-2',2',3'-trimethylcyclopent-3-enyl)but-3-en-2-one (a mixture of E:Z-isomers (7:2-ratio) - Odour description: floral, ionone alpha, woody, fruity.

Prepared from campholytic aldehyde derived from (R)-campholenic aldehyde (ca. 80% ee)

= (-)-(3E/Z)-4-[(1'R)-2',2',3'-trimethylcyclopent-3-en-1-yl]but-3-en-2-one

Ref: Jerzy A. Bajgrowicz, Urs Mueller, CYCLOPENTANE/CYCLOPENTENE ALDEHYDE OR KETONE DERIVATIVES AND THEIR USE AS ODORANTS, United States Patent Application 20090298950 (December 3, 2009)

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(+)-(3E/Z)-4-((1'S)-2',2',3'-trimethylcyclopent-3-enyl)but-3-en-2-one (a mixture of E:Z-isomers (7:2-ratio) - Odour description: agrestic, woody (thujone-type), sweet, powdery, ionone, floral, creamy.

Prepared from campholytic aldehyde derived from (S)-campholenic aldehyde (ca. 30% ee)

= (+)-(3E/Z)-4-[(1'S)-2',2',3'-trimethylcyclopent-3-en-1-yl]but-3-en-2-one

Ref: Jerzy A. Bajgrowicz, Urs Mueller, CYCLOPENTANE/CYCLOPENTENE ALDEHYDE OR KETONE DERIVATIVES AND THEIR USE AS ODORANTS, United States Patent Application 20090298950 (December 3, 2009)

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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