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

The Sotolons =

4,5-dimethyl-3-hydroxy-2(5H)-furanone

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Photo by permission of M. Roudintska - Art & Parfum

(+)-(S)-Sotolone - curry, walnut (strongly caramelic)

Odor threshold = 0.8 ppb (in 12% EtOH/Water V/V)

Sotolon is also known as caramel furanone, sugar lactone and fenugreek lactone - it has the typical aroma of fenugreek or curry at high concentrations and caramel, maple syrup and burnt sugar at lower concentrations.

= (+)-(5S)-3-hydroxy-4,5-dimethylfuran-2(5H)-one

Ref: Pons, A.; Lavigne, V.; Landais, Y.; Darriet, P.; Dubourdieu, D., Distribution and Organoleptic Impact of Sotolon Enantiomers in Dry White Wines, J. Agric. Food Chem.; (Article); 2008; 56(5); 1606-1610; Guichard, E.; Fournier, N. Enantiomeric ratios of sotolon in different media and sensory differentiation of the pure enantiomers, In European Food Chemistry VI; Hambourg, 1991.

(-)-(R)-Sotolone - walnut, rancid. Although the aromatic nuances of both enantiomers were quite similar, the perception threshold of (S)-sotolon in dilute alcohol solution (12% vol) was >100 times lower than that of (R)-sotolon.

Odor threshold = 89 ppb (in 12% EtOH/Water V/V)

= (-)-(5R)-3-hydroxy-4,5-dimethylfuran-2(5H)-one

Ref: Ref: Pons, A.; Lavigne, V.; Landais, Y.; Darriet, P.; Dubourdieu, D., Distribution and Organoleptic Impact of Sotolon Enantiomers in Dry White Wines, J. Agric. Food Chem.; (Article); 2008; 56(5); 1606-1610; Guichard, E.; Fournier, N. Enantiomeric ratios of sotolon in different media and sensory differentiation of the pure enantiomers, In European Food Chemistry VI; Hambourg, 1991.

Cyclic Terpenoid Odorants

Bicyclic Terpenoid Odorants

Acyclic Terpenoid Odorants

Ionones, Irones, Damascones & Structurally Related Odorants

Acyclics (Alcohols, Esters, Acids, Aldehydes)

Lactones & Furanones

Sesquiterpenoid Related Odorants

Steroid Urine Type Odorants

Sandalwood Type Odorants

Musk Odorants

Miscellaneous

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