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

The 2,3-Methano-3,7-dimethyl-6-octen-1-ols

(The Cyclopropanated Analogues of Geraniol & Nerol)

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Photo by permission of M. Roudintska - Art & Parfum

(+)-(2S,3S)-2,3-Methano-3,7-dimethyl-6-octen-1-ol - Woody rosy odor with sweetness of nerol; similar to, but more woody than the racemate.

The racemate is described as Slightly woody, heavy rosy odor, less intensive and characteristic than geraniol

= (+)-((1S,2S)-2-methyl-2-(4-methylpent-3-enyl)cyclopropyl)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

(-)-(2R,3R)-2,3-Methano-3,7-dimethyl-6-octen-1-ol - Woody rosy odor close to the racemate, a little bit more woody

The racemate is described as Slightly woody, heavy rosy odor, less intensive and characteristic than geraniol

= (-)-((1R,2R)-2-methyl-2-(4-methylpent-3-enyl)cyclopropyl)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

(+)-(2R,3S)-2,3-Methano-3,7-dimethyl-6-octen-1-ol - Woody rosy odor with aromatic aspect reminiscent of sulfrol found in the top note of sandalwood oil

The racemate is described as Floral-rosy odor with somewhat spicy green aspect, less intensive than nerol

= (+)-((1R,2S)-2-methyl-2-(4-methylpent-3-enyl)cyclopropyl)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-3,7-dimethyl-6-octen-1-ol - Nerol-like odor (floral-rosy), but less intensive than the racemate.

The racemate is described as Floral-rosy odor with somewhat spicy green aspect, less intensive than nerol

= (-)-((1S,2R)-2-methyl-2-(4-methylpent-3-enyl)cyclopropyl)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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