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

The 2-Propyl-4-(2,2,3-trimethyl-cyclopent-3-enyl)-but-2-en-1-ols

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Photo by permission of M. Roudintska - Art & Parfum

(1'R,E)-(+)-2-Propyl-4-(2',2',3'-trimethyl-cyclopent-3-enyl)-but-2-en-1-ol - soft and warm sandalwood oil odor (Aida, et. al.); Chapuis indicates - woody, sandalwood

= (+)-(2E)-2-{2-[(1R)-2,2,3-trimethylcyclopent-3-en-1-yl]ethylidene}pentan-1-ol

Ref: Aida, et. al., United States Patent 6,084,138, July 4, 2000; Christian Chapuis, In the Quest for a Virtual Pseudo Receptor for Sandalwood-Like Odorants, Part I, Chemistry & Biodiversity, Volume 1, Issue 7, Date: July 2004, Pages: 980-1021

Note - Chapuis indicates that this has the (+)-optical rotation and states "It is worthy of note that the chiroptical properties of alcohols (10) are very close to zero and may be influenced either by the solvent used, or by the presence of trace contaminants such as the (Z)- or homoallylic alcohols.

Aida reports the optical rotation as AlphaD5= -0.23

(1'S,E)-(-)-2-Propyl-4-(2,2,3-trimethyl-cyclopent-3-enyl)-but-2-en-1-ol - Chapuis indicates - slightly sandalwood, weak

= (-)-(2E)-2-{2-[(1S)-2,2,3-trimethylcyclopent-3-en-1-yl]ethylidene}pentan-1-ol

Ref: Christian Chapuis, In the Quest for a Virtual Pseudo Receptor for Sandalwood-Like Odorants, Part I, Chemistry & Biodiversity, Volume 1, Issue 7, Date: July 2004, Pages: 980-1021

Note - Chapuis indicates that this has the (-)-optical rotation and states "It is worthy of note that the chiroptical properties of alcohols (10) are very close to zero and may be influenced either by the solvent used, or by the presence of trace contaminants such as the (Z)- or homoallylic alcohols.

(1'R,Z)-(-)-2-Propyl-4-(2',2',3'-trimethyl-cyclopent-3-enyl)-but-2-en-1-ol - green, vaguely fruity, woody

= (-)-(2Z)-2-{2-[(1R)-2,2,3-trimethylcyclopent-3-en-1-yl]ethylidene}pentan-1-ol

Ref: Christian Chapuis, In the Quest for a Virtual Pseudo Receptor for Sandalwood-Like Odorants, Part I, Chemistry & Biodiversity, Volume 1, Issue 7, Date: July 2004, Pages: 980-1021

(1'S,Z)-(+)-2-Propyl-4-(2',2',3'-trimethyl-cyclopent-3-enyl)-but-2-en-1-ol - woody, very weak

= (+)-(2Z)-2-{2-[(1S)-2,2,3-trimethylcyclopent-3-en-1-yl]ethylidene}pentan-1-ol

Ref: Christian Chapuis, In the Quest for a Virtual Pseudo Receptor for Sandalwood-Like Odorants, Part I, Chemistry & Biodiversity, Volume 1, Issue 7, Date: July 2004, Pages: 980-1021

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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