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

The Polywoods®

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Photo by permission of M. Roudintska - Art & Parfum

(+)-(2R,4aR,8aS)-Polywood® - Odor properties: described as exhibiting a rich, voluminous woody note with a powdery ionone-like undertone.

Commercial racemic Polywood is decribed as having a tenacious and elegant woody note.

= (+)-(2R,4aR,8aS)-5,5,8a-trimethyldecahydro-naphthalen-2-yl acetate or (+)-(2R,4aR,8aS)- perhydro-5,5,8a-trimethyl-2-naphthalenyl acetate

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; Paul A. Stadler, Albert Eschenmoser, Erling Sundt, Oxygenated decalin derivatives, United States Patent 3,989,739 (November 2, 1976); Paul A. Stadler, Albert Eschenmoser, Erling Sundt, Perfume compositions including oxygenated decalin derivatives, United States Patent 3,928,246 (December 23, 1975); see also Elisabetta Brenna, Claudio Fuganti and Stefano Serra, Enantioselective perception of chiral odorants, Tetrahedron: Asymmetry, 14, 1–42 (2003)

Polywood® is a registered trademark of Firmenich SA

(-)-(2S,4aS,8aR)-Polywood® - Odor properties: was found less rich than (+)-(2R,4aR,8aS)-Polywood®, still woody, dry, and amber-like.

= (-)-((2S,4aS,8aR)-5,5,8a-trimethyldecahydro-naphthalen-2-yl acetate or (-)-(2S,4aS,8aR)- perhydro-5,5,8a-trimethyl-2-naphthalenyl acetate

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; Paul A. Stadler, Albert Eschenmoser, Erling Sundt, Oxygenated decalin derivatives, United States Patent 3,989,739 (November 2, 1976); Paul A. Stadler, Albert Eschenmoser, Erling Sundt, Perfume compositions including oxygenated decalin derivatives, United States Patent 3,928,246 (December 23, 1975); see also Elisabetta Brenna, Claudio Fuganti and Stefano Serra, Enantioselective perception of chiral odorants, Tetrahedron: Asymmetry, 14, 1–42 (2003)

Polywood® is a registered trademark of Firmenich SA

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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