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

The Maple Furanones

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Photo by permission of M. Roudintska - Art & Parfum

c

(S)-(-)-Maple furanone - less intense than the (R)-(+)-Maple furanone enantiomer.

= (5S)-(-)-5-ethyl-3-hydroxy-4-methylfuran-2(5H)-one

Ref: Atsufumi Nakahashi, Yoshihiro Yaguchi, Nobuaki Miura, Makoto Emura, and Kenji Monde, A Vibrational Circular Dichroism Approach to the Determination of the Absolute Configurations of Flavorous 5-Substituted-2(5H)-furanones, J. Nat. Prod., Article ASAP, Publication Date (Web): March 7, 2011

c

 

(R)-(+)-Maple furanone - possessed a significantly intense maple syrup-like odor at 100 ppt solution in H2O, while (S)-(-)-Maple furanone was less intense.

= (5R)-(+)-5-ethyl-3-hydroxy-4-methylfuran-2(5H)-one

Ref: Atsufumi Nakahashi, Yoshihiro Yaguchi, Nobuaki Miura, Makoto Emura, and Kenji Monde, A Vibrational Circular Dichroism Approach to the Determination of the Absolute Configurations of Flavorous 5-Substituted-2(5H)-furanones, J. Nat. Prod., Article ASAP, Publication Date (Web): March 7, 2011

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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