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

The Helvetolides®

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Photo by permission of M. Roudintska - Art & Parfum

(+)-Helvetolide® - Odor properties: musky, ambrette, pear - described as more intense and more musky than the (- )-enantiomer, which was however found quite similar in tonality... The fragrance effect imparted by the above-cited preferred compound of the invention is even more powerful and muskier when said compound is used in the form of one of its optically active isomers, i.e., (+)-Helvetolide

Odor Threshold = 1.1 ng/L (in air)

= (+)-(1'R,4S)-4-(3',3'-dimethyl-1'-cyclohexyl)-2,2-dimethyl-3-oxapentyl propanoate

Ref: Wolfgang K. Giersch, Karl-Heinrich Schulte-Elte, Cyril Mahaim, Esters and their use in perfumery, United States Patent 5,166,412 (November 24, 1992); Elisabetta Brenna, Claudio Fuganti and Stefano Serra, Enantioselective perception of chiral odorants, Tetrahedron: Asymmetry, 14, 1–42 (2003); Threshold value from Philip Kraft and Walter Eichenberger, Synthesis and Odor of Aliphatic Musks: Discovery of a New Class of Odorants, Eur. J. Org. Chem. 2004, 354-365

Helvetolide® is a registered trademark of Firmenich SA

(-)-(1'S,4R)-Helvetolide® - Odor properties: nicely musky and ambrette, pear, floral.

= (-)-(1'S,4R)-4-(3',3'-dimethyl-1'-cyclohexyl)-2,2-dimethyl-3-oxapentyl propanoate

Ref: Wolfgang K. Giersch, Karl-Heinrich Schulte-Elte, Cyril Mahaim, Esters and their use in perfumery, United States Patent 5,166,412 (November 24, 1992); Elisabetta Brenna, Claudio Fuganti and Stefano Serra, Enantioselective perception of chiral odorants, Tetrahedron: Asymmetry, 14, 1–42 (2003)

Helvetolide® is a registered trademark of Firmenich SA

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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