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

The 6-Acetoxy-1,8-cineoles

You must have installed the Chime plugin to view the molecular visualization on this page

Photo by permission of M. Roudintska - Art & Parfum

(1S,4R,6S)-(+)-6-Acetoxy-1,8-cineole - woody (weak)

Ref: H. K. Kubota, et. al., J. Agric. Food Chem., 47, No. 2, 685-689 (1999)

Also called (1S,4R,2S)-(+)-2-Acetoxy-1,8-cineole

In contrast to Kubota's report, Mitsuo Miyazawa and Yuya Hashimoto (Microbial resolution of racemic 2-endo-acetoxy-1,8-cineole by Glomerella cingulata, Tetrahedron: Asymmetry, Volume 12, Issue 22, 10 December 2001, Pages 3185-3187) report that "both (+)-2-endo-acetoxy-1,8-cineole and (-)-2-endo-hydroxy-1,8-cineole could be quantitatively obtained in enantiomerically pure form (yield 50%; e.e. 100%). In addition, the odor differences between the enantiomers are also described. In both compounds (acetoxy and hydroxy), the (+)-enantiomers tended to have more bright, light and sweet odors than their (-)-antipodes."

(1R,4S,6R)-(-)-6-Acetoxy-1,8-cineole - woody, Alpinia galanga like and stronger than the (1S,4R,6S)- isomer

Ref: H. K. Kubota, et. al., J. Agric. Food Chem., 47, No. 2, 685-689 (1999)

Also called (1R,4S,2R)-(-)-2-Acetoxy-1,8-cineole

(1S,4R,6R)-6-Acetoxy-1,8-cineole - weak

Also called (1S,4R,2R)-2-Acetoxy-1,8-cineole

Ref: H. K. Kubota, et. al., J. Agric. Food Chem., 47, No. 2, 685-689 (1999)

(1R,4S,6S)-6-Acetoxy-1,8-cineole - fruity, sweet

Also called (1R,4S,2S)-2-Acetoxy-1,8-cineole

Ref: H. K. Kubota, et. al., J. Agric. Food Chem., 47, No. 2, 685-689 (1999)

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

HOME

Copyright 2001 - Leffingwell & Associates