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

The 2,3-Methano-1-pentanols

(The Cyclopropanated Analogues of nor-Leaf alcohol)

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Photo by permission of M. Roudintska - Art & Parfum

(+)-(2R,3S)-2,3-Methano-1-pentanol - Difusive ether green odor, close to nor-leaf alcohol, more green than the racemate or its enantiomer

The racemate is described as Acidic ether fruity odor, less green than nor-leaf alcohol (cis-2-penten-1-ol).

= (+)-((1R,2S)-2-ethylcyclopropyl)methanol

Ref: Hiroki Asao, Hiroyuki Sakauchi, Shigefumi Kuwahara and Hiromasa Kiyota, Synthesis and odor description of optically active cyclopropanated analogues of geraniol, nerol, nor-leaf alcohol, and matsutake alcohol, Tetrahedron: Asymmetry, 18 (2007) 537–541

(-)-(2S,3R)-2,3-Methano-1-pentanol - Weak rosy odor without characteristic green aspect found in the racemate

The racemate is described as Acidic ether fruity odor, less green than nor-leaf alcohol (cis-2-penten-1-ol).

= (-)-((1S,2R)-2-ethylcyclopropyl)methanol

Ref: Hiroki Asao, Hiroyuki Sakauchi, Shigefumi Kuwahara and Hiromasa Kiyota, Synthesis and odor description of optically active cyclopropanated analogues of geraniol, nerol, nor-leaf alcohol, and matsutake alcohol, Tetrahedron: Asymmetry, 18 (2007) 537–541

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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