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

The 5,5,8a-trimethyloctahydronaphthalen-2(1H)-ones

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Photo by permission of M. Roudintska - Art & Parfum

(-)-(4aS,8aR)-5,5,8a-trimethyloctahydronaphthalen-2(1H)-one - Odor properties: described as strong, woody amber-like, with a distinct note of damp earth, cellar, geosmin.

Ref: Antoine Gautier, Christian Vial, Cedric Morel, Marina Lander, Ferdinand Naef, Preparation and Odor Evaluation of Both Enantiomers of 3,4,4aa,5,6,7,8,8aß-Octahydro-5,5,8aß-trimethyl-2(1H)-naphthalenone and 1,2a,3,4,4aa5,6,7,8,8aß-Decahydro-5,5,8aß-trimethyl-2ß-naphthalenyl Acetate, Four Woody Odorants, Helv.Chim.Acta 1987, 70: 2039-2044; see also Elisabetta Brenna, Claudio Fuganti and Stefano Serra, Enantioselective perception of chiral odorants, Tetrahedron: Asymmetry, 14, 1–42 (2003)

(+)-(4aR,8aS)-5,5,8a-trimethyloctahydronaphthalen-2(1H)-one - Odor properties: was found as woody, patchouli like, and less strong than its enantiomer.

Ref: Antoine Gautier, Christian Vial, Cedric Morel, Marina Lander, Ferdinand Naef, Preparation and Odor Evaluation of Both Enantiomers of 3,4,4aa,5,6,7,8,8aß-Octahydro-5,5,8aß-trimethyl-2(1H)-naphthalenone and 1,2a,3,4,4aa5,6,7,8,8aß-Decahydro-5,5,8aß-trimethyl-2ß-naphthalenyl Acetate, Four Woody Odorants, Helv.Chim.Acta 1987, 70: 2039-2044; see also Elisabetta Brenna, Claudio Fuganti and Stefano Serra, Enantioselective perception of chiral odorants, Tetrahedron: Asymmetry, 14, 1–42 (2003)

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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