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

Rhubafuran®

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Photo by permission of M. Roudintska - Art & Parfum

(-)-(2R,4S)-Rhubafuran® - The most pleasant one, floral, linalool-like, rhubarb and citrus, green, slightly eucalyptus. (2R,4S)-, followed by its enantiomer, are the closest to the commercial Rhubafuran. [Purity of 97%; 99% ee]

= (-)-(2R,4S)-2,4-dimethyl-4-phenyltetrahydrofuran

Ref: Agnese Abate, Elisabetta Brenna, Giovanni Fronza, Claudio Fuganti, Francesco G. Gatti, Stefano Serra, and Enrica Zardoni, Preparation of the Enantiomerically Enriched Isomers of the Odorous Cyclic Ethers Clarycet® , Florol® , and Rhubafuran® by Enzymatic Catalysis, Helv. Chim. Acta, Vol. 87, 765-780 (2004)

Rhubafuran® is a trademark of Quest International

(+)-(2S,4R)-Rhubafuran® - Citric, rhubarb, slightly green, slightly animalic. [Purity of 97%; 99% ee]

= (+)-(2S,4R)-2,4-dimethyl-4-phenyltetrahydrofuran

Ref: Agnese Abate, Elisabetta Brenna, Giovanni Fronza, Claudio Fuganti, Francesco G. Gatti, Stefano Serra, and Enrica Zardoni, Preparation of the Enantiomerically Enriched Isomers of the Odorous Cyclic Ethers Clarycet® , Florol® , and Rhubafuran® by Enzymatic Catalysis, Helv. Chim. Acta, Vol. 87, 765-780 (2004)

Rhubafuran® is a trademark of Quest International

(-)-(2S,4S)-Rhubafuran® - Grapefruit-like, bitter, cassis, slightly oxane-like and reminiscent of dimethyloctenone. Dry down (24 h) bitter, grapefruit, oxane. [99% ee]

= (-)-(2S,4S)-2,4-dimethyl-4-phenyltetrahydrofuran

Ref: Agnese Abate, Elisabetta Brenna, Giovanni Fronza, Claudio Fuganti, Francesco G. Gatti, Stefano Serra, and Enrica Zardoni, Preparation of the Enantiomerically Enriched Isomers of the Odorous Cyclic Ethers Clarycet® , Florol® , and Rhubafuran® by Enzymatic Catalysis, Helv. Chim. Acta, Vol. 87, 765-780 (2004)

Rhubafuran® is a trademark of Quest International

(+)-(2R,4R)-Rhubafuran® - Nuts, acidic, animalic, slightly rhubarb. [Purity of 97%; 99% ee]

= (+)-(2R,4R)-2,4-dimethyl-4-phenyltetrahydrofuran

Ref: Agnese Abate, Elisabetta Brenna, Giovanni Fronza, Claudio Fuganti, Francesco G. Gatti, Stefano Serra, and Enrica Zardoni, Preparation of the Enantiomerically Enriched Isomers of the Odorous Cyclic Ethers Clarycet® , Florol® , and Rhubafuran® by Enzymatic Catalysis, Helv. Chim. Acta, Vol. 87, 765-780 (2004)

Rhubafuran® is a trademark of Quest International

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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