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

The 3-Acetoxy-1,8-cineoles

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Photo by permission of M. Roudintska - Art & Parfum

(1S,3R,4R)-3-acetoxy-1,8-cineole - sweet floral, weak

 Also called (1S,4R,5R)-5-Acetoxy-1,8-cineole

= (1S,3R,4R)-1,5,5-trimethyl-6-oxa-bicyclo[2.2.2]octan-3-yl acetate

= (1S,4R,5R)-1,3,3-trimethyl-2-oxabicyclo[2.2.2]oct-5-yl acetate

Ref: Kubota, Kikue, Yuki Someya, Reiko Yoshida, Akio Kobayashi, Tetsu-ichiro Morita, and Hiroyuki Koshino. "Enantiomeric Purity and Odor Characteristics of 2-and 3-Acetoxy-1, 8-cineoles in the Rhizomes of Alpinia galanga Willd." Journal of agricultural and food chemistry 47, no. 2 (1999): 685-689; Kubota, Kikue, Yuki Someya, Yoshiko Kurobayashi, and Akio Kobayashi. "Flavor Characteristics and Stereochemistry of the Volatile Constituents of Greater Galangal (Alpinia Galanga Willd.)." In Flavor Chemistry of Ethnic Foods, pp. 97-104. Springer US, 1999

(1R,3S,4S)-3-Acetoxy-1,8-cineole - sweet floral, weak

Also called (1R,4S,5S)-5-Acetoxy-1,8-cineole

= (1R,3S,4S)-1,5,5-trimethyl-6-oxa-bicyclo[2.2.2]octan-3-yl acetate

= (1R,4S,5S)-1,3,3-trimethyl-2-oxabicyclo[2.2.2]oct-5-yl acetate

Ref: Kubota, Kikue, Yuki Someya, Reiko Yoshida, Akio Kobayashi, Tetsu-ichiro Morita, and Hiroyuki Koshino. "Enantiomeric Purity and Odor Characteristics of 2-and 3-Acetoxy-1, 8-cineoles in the Rhizomes of Alpinia galanga Willd." Journal of agricultural and food chemistry 47, no. 2 (1999): 685-689; Kubota, Kikue, Yuki Someya, Yoshiko Kurobayashi, and Akio Kobayashi. "Flavor Characteristics and Stereochemistry of the Volatile Constituents of Greater Galangal (Alpinia Galanga Willd.)." In Flavor Chemistry of Ethnic Foods, pp. 97-104. Springer US, 1999

(1S,3S,4R)-(+)-3-Acetoxy-1,8-cineole - camphoraceous (Kubota, et al.); camphor-like, smooth (Loandos et al.)

Also called (1S,4R,5S)-5-Acetoxy-1,8-cineole

= (1S,3S,4R)-1,5,5-trimethyl-6-oxa-bicyclo[2.2.2]octan-3-yl acetate

= (1S,4R,5S)-1,3,3-trimethyl-2-oxabicyclo[2.2.2]oct-5-yl acetate

Ref: Kubota, Kikue, Yuki Someya, Reiko Yoshida, Akio Kobayashi, Tetsu-ichiro Morita, and Hiroyuki Koshino. "Enantiomeric Purity and Odor Characteristics of 2-and 3-Acetoxy-1, 8-cineoles in the Rhizomes of Alpinia galanga Willd." Journal of agricultural and food chemistry 47, no. 2 (1999): 685-689; Kubota, Kikue, Yuki Someya, Yoshiko Kurobayashi, and Akio Kobayashi. "Flavor Characteristics and Stereochemistry of the Volatile Constituents of Greater Galangal (Alpinia Galanga Willd.)." In Flavor Chemistry of Ethnic Foods, pp. 97-104. Springer US, 1999; Loandos, María del H., Margarita B. Villecco, Eleuterio Burgueño-Tapia, Pedro Joseph-Nathan and César A. N. Catalán, Preparation and Absolute Configuration of (1R,4R)-(+)-3-Oxo-, (1S,4S)-(-)-3-Oxo- and (1R,3S,4R)- (+)-3-Acetyloxy-5-oxo-1,8-cineole, Natural product communications 4, no. 11 (2009): 1537-1545.

(1R,3R,4S)-(-)-3-Acetoxy-1,8-cineole - mild woody (Kubota, et al.); woody (Loandos et al.)

Also called (1R,4S,5R)-5-Acetoxy-1,8-cineole

= (1R,3R,4S)-1,5,5-trimethyl-6-oxa-bicyclo[2.2.2]octan-3-yl acetate

= (1R,4S,5R)-1,3,3-trimethyl-2-oxabicyclo[2.2.2]oct-5-yl acetate

Ref: Kubota, Kikue, Yuki Someya, Reiko Yoshida, Akio Kobayashi, Tetsu-ichiro Morita, and Hiroyuki Koshino. "Enantiomeric Purity and Odor Characteristics of 2-and 3-Acetoxy-1, 8-cineoles in the Rhizomes of Alpinia galanga Willd." Journal of agricultural and food chemistry 47, no. 2 (1999): 685-689; Kubota, Kikue, Yuki Someya, Yoshiko Kurobayashi, and Akio Kobayashi. "Flavor Characteristics and Stereochemistry of the Volatile Constituents of Greater Galangal (Alpinia Galanga Willd.)." In Flavor Chemistry of Ethnic Foods, pp. 97-104. Springer US, 1999; Loandos, María del H., Margarita B. Villecco, Eleuterio Burgueño-Tapia, Pedro Joseph-Nathan and César A. N. Catalán, Preparation and Absolute Configuration of (1R,4R)-(+)-3-Oxo-, (1S,4S)-(-)-3-Oxo- and (1R,3S,4R)- (+)-3-Acetyloxy-5-oxo-1,8-cineole, Natural product communications 4, no. 11 (2009): 1537-1545.

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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