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

The alpha-Ambrinols

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Photo by permission of M. Roudintska - Art & Parfum

(2S, 4aS)-(-)-alpha-ambrinol - powerful amber note with a natural, somewhat musky and animal character (Ohloff); animal, indole, or skatol-like naphthalenic odour properties (Naegeli & Wirz-Habersack)

= (2S, 4aS)-(-)- 2,5,5-Trimethyl-1,2,3,4,4a,5,6,7-octahydro-naphthalen-2-ol

Ref: Ohloff, G., Fragrance Chemistry, p. 546, Academic Press, New York, 1982; P. Naegeli and Y. Wirz-Habersack, Enantiodifferentiation of odour perception of alpha-ambrinols, Tetrahedron: Asymmetry, Volume 3, Issue 2, 1992, Pages 221-222

(2R, 4aR)-(+)-alpha-ambrinol - exhibits a strongly dry earthy, musty tonality, reminiscent of geosmine.

= (2R, 4aR)-(+)- 2,5,5-Trimethyl-1,2,3,4,4a,5,6,7-octahydro-naphthalen-2-ol

Ref: P. Naegeli and Y. Wirz-Habersack, Enantiodifferentiation of odour perception of alpha-ambrinols, Tetrahedron: Asymmetry, Volume 3, Issue 2, 1992, Pages 221-222

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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