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

The gamma-Undecalactones

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

(S)-(-)-4-heptylbutan-4-olide - fatty-sweet aldehyde note less intense than its enantiomer (Mosandl & Gunther, Evaluated as a 1% solution on blotter strips); sweet, coconut (Yamamoto)

Threshold = 12 ppb in water (Yamamoto)

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

Ref: Armin Mosandl & Claus Gunther, Stereoisomeric Flavor Compounds. 20. Structure and Properties of gamma-lactone Enantiomers, J. Agric. Food Chem., 1989, 37, 413-418; Mans H. Boelens, Harrie Boelens & Leo J. van Gemert, Perfumer & Flavorist, Vol. 18, No. 6, 1-15, 1993; Takeshi Yamamoto, Advances in the Transition Metal (Rh, RU)-Binap-Catalyzed Asymmetric Synthesis of Chral Compounds for Flavours and Fragrances and Their Associated Sensory Properties, in Current Topics in Flavours and Fragrances - Towards a New Millennium of Discovery, by K.A. Swift (Editor), Kluwer Academic Publishers, Dordrecht NL, 2000, pp. 33-58

(R)-(+)-4-heptylbutan-4-olide - strong, fatty-sweet, reminiscent of peach, with some bloomy aspects (Mosandl & Gunther, Evaluated as a 1% solution on blotter strips); strong, sweet, coconut (Yamamoto)

Threshold = 4 ppb in water (Yamamoto)

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

Ref: Armin Mosandl & Claus Gunther, Stereoisomeric Flavor Compounds. 20. Structure and Properties of gamma-lactone Enantiomers, J. Agric. Food Chem., 1989, 37, 413-418; Mans H. Boelens, Harrie Boelens & Leo J. van Gemert, Perfumer & Flavorist, Vol. 18, No. 6, 1-15, 1993; Takeshi Yamamoto, Advances in the Transition Metal (Rh, RU)-Binap-Catalyzed Asymmetric Synthesis of Chral Compounds for Flavours and Fragrances and Their Associated Sensory Properties, in Current Topics in Flavours and Fragrances - Towards a New Millennium of Discovery, by K.A. Swift (Editor), Kluwer Academic Publishers, Dordrecht NL, 2000, pp. 33-58

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