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

The 1,2-Methano-3-octanols

(The Cyclopropanated Analogues of 1-octen-3-ol)

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Photo by permission of M. Roudintska - Art & Parfum

(-)-(R)-1,2-Methano-3-octanol - Sweet matsutake-like (mushroom-like) odor, close to natural (R)-matsutakeol (natural 1-octen-3-ol)

The racemate is described as Unpleasant sweet-sour, fatty, woody, rosy odor, lacking in mushroom-like aspect in natural (R)-matsutakeol (natural 1-octen-3-ol)

= (-)-(R)-1-cyclopropylhexan-1-ol

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

(+)-(S)-1,2-Methano-3-octanol - Humid mossy rosy odor, no mushroom character as found in the racemate

The racemate is described as Unpleasant sweet-sour, fatty, woody, rosy odor, lacking in mushroom-like aspect in natural (R)-matsutakeol (natural 1-octen-3-ol)

= (+)-(S)-1-cyclopropylhexan-1-ol

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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