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

The 2,5,5,8a-tetramethyl-3,5,6,7,8,8A-hexahydro-1(2H)-naphthalenones

You must have Java installed to view the molecular visualization on this page
Photo by permission of M. Roudintska - Art & Parfum

(+)-(2S,8aR)-2,5,5,8a-tetramethyl-3,5,6,7,8,8a-hexahydronaphthalen-1(2H)-one - The two enantiomers of this compounds, namely (2S,8aR)-2,5,5,8a-tetramethyl-3,5,6,7,8,8A-hexahydro-1(2H)-naphthalenone and (2R,8aS)-2,5,5,8a-tetramethyl-3,5,6,7,8,8A-hexahydro-1(2H)-naphthalenone, although having organoleptic properties similar to the racemate, display different intensities, the (2S,8aR) enantiomer being more powerful than the (2R,8aS) enantiomer.

The racemate is described as having an odour with woody (earthy-patchouli type), powdery and ionone (violet) notes. In fact, this unique combination of odour notes can give the impression of a nice woody, irone and slightly patchouli scent.

= (2S,8aR)-2,3,6,7,8,8a-hexahydro-2,5,5,8a-tetramethylnaphthalen-1(5H)-one

Ref: Charles Fehr & Iris Farris; Naphthalenone Derivative with Powdery-Ionone Type Odors, United States Patent Application 20080214419 (September 4, 2008)

(-)-(2R,8aS)-2,5,5,8a-tetramethyl-3,5,6,7,8,8A-hexahydro-1(2H)-naphthalenone - The two enantiomers of this compounds, namely (2S,8aR)-2,5,5,8a-tetramethyl-3,5,6,7,8,8A-hexahydro-1(2H)-naphthalenone and (2R,8aS)-2,5,5,8a-tetramethyl-3,5,6,7,8,8A-hexahydro-1(2H)-naphthalenone, although having organoleptic properties similar to the racemate, display different intensities, the (2S,8aR) enantiomer being more powerful than the (2R,8aS) enantiomer.

The racemate is described as having an odour with woody (earthy-patchouli type), powdery and ionone (violet) notes. In fact, this unique combination of odour notes can give the impression of a nice woody, irone and slightly patchouli scent.

= (2R,8aS)-2,3,6,7,8,8a-hexahydro-2,5,5,8a-tetramethylnaphthalen-1(5H)-one

Ref: Charles Fehr & Iris Farris; Naphthalenone Derivative with Powdery-Ionone Type Odors, United States Patent Application 20080214419 (September 4, 2008)

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

HOME

Copyright 2001-2002 - Leffingwell & Associates