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

The gamma-Octalactones

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Photo by permission of M. Roudintska - Art & Parfum

(S)-(-)-4-butylbutan-4-olide - fatty coconut note, less intense than (R)-isomer (Mosandl & Gunther, Evaluated as a 1% solution on blotter strips)

Odor Threshold = 130 ppb in water (Yamamoto)

Odor Threshold = 135 ppb in red wine (R.C. Brown)

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

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; Rachel Christine Brown, gamma-Lactones in wine: Synthesis, quantification and sensory studies, Ph.D. Thesis, Flinders University of South Australia, November 2007; 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,

(R)-(+)-4-butylbutan-4-olide - spicy-green, coconut note, with almond notes (Mosandl & Gunther, Evaluated as a 1% solution on blotter strips)

Odor Threshold = 300 ppb in water (Yamamoto)

Odor Threshold = 238 ppb in red wine (R.C. Brown)

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

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; Rachel Christine Brown, gamma-Lactones in wine: Synthesis, quantification and sensory studies, Ph.D. Thesis, Flinders University of South Australia, November 2007; 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,

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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