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

The gamma-Decalactones

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

(S)-(-)-4-hexylbutan-4-olide - soft, sweet coconut note with fruity-fatty aspects (Mosandl & Gunther, Evaluated as a 1% solution on blotter strips); Bourdineaud et. al. describe this as: Fruity, banana like, lactonic and jasmonic like floral top note. Base note is closest to that of the racemate with more volume, less sweet and floral, but heavier and more lactonic.

Odor Threshold = 47 ppb in red wine (R.C. Brown)

Also known as (S)-(-)-gamma-decalactone

Ref: A. Mosandl and C. Gunther, J. Agric. Food Chem., 37, 413-416 (1989); Mans H. Boelens, Harrie Boelens & Leo J. van Gemert, Perfumer & Flavorist, Vol. 18, No. 6, 1-15, 1993; Bourdineaud, Jean-Paul; Ehret, Charles; Petrzilka, Martin; Optically active lactones, World Patent WO/94107887, April 19, 1994; Rachel Christine Brown, gamma-Lactones in wine: Synthesis, quantification and sensory studies, Ph.D. Thesis, Flinders University of South Australia, November 2007

(R)-(+)-4-hexylbutan-4-olide - strong, fatty-sweet fruity note, some reminiscence to coconut, caramel (Mosandl & Gunther, Evaluated as a 1% solution on blotter strips); Bourdineaud et. al. describe this as: Fatty, animalic top note. Upon evaporation clearly different from the racemate with regard to the acidic and animalic base notes; In particular suitable for flavours.

Odor Threshold = 34 ppb in red wine (R.C. Brown)

Also known as (R)-(+)-gamma-decalactone

Ref: A. Mosandl and C. Gunther, J. Agric. Food Chem., 37, 413-416 (1989); Mans H. Boelens, Harrie Boelens & Leo J. van Gemert, Perfumer & Flavorist, Vol. 18, No. 6, 1-15, 1993; Bourdineaud, Jean-Paul; Ehret, Charles; Petrzilka, Martin; Optically active lactones, World Patent WO/94107887, April 19, 1994; Rachel Christine Brown, gamma-Lactones in wine: Synthesis, quantification and sensory studies, Ph.D. Thesis, Flinders University of South Australia, November 2007

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