(1S,2S,4R)-(+)-2-Acetoxy-1,8-cineole - woody (weak) - Kubota et al.; Sharp, fruity, sweet odor - Miyazawa and Hashimoto Also called (1S,4R,6S)-(+)-6-Acetoxy-1,8-cineole =(1S,2S,4R)-1,5,5-trimethyl-6-oxa-bicyclo[2.2.2]octan-2-yl acetate = (1S,4R,6S)-1,3,3-trimethyl-2-oxabicyclo[2.2.2]oct-6-yl acetate In contrast to Kubota's report, Mitsuo Miyazawa and Yuya Hashimoto 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." Ref: 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; 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; 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

(1R,2R,4S)-(-)-2-Acetoxy-1,8-cineole - woody, Alpinia galanga like and stronger than the (1S,2S,4R)- isomer - Kubota et al; Camphorous, dry odor - Miyazawa and Hashimoto Also called (1R,4S,6R)-(-)-6-Acetoxy-1,8-cineole = (1R,2R,4S)-1,5,5-trimethyl-6-oxa-bicyclo[2.2.2]octan-2-yl acetate = (1R,4S,6R)-1,3,3-trimethyl-2-oxabicyclo[2.2.2]oct-6-yl acetate Ref: 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; 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.

(1S,2R,4R)-2-Acetoxy-1,8-cineole - weak Also called (1S,4R,6R)-6-Acetoxy-1,8-cineole = (1S,2R,4R)-1,5,5-trimethyl-6-oxa-bicyclo[2.2.2]octan-2-yl acetate = (1S,4R,6R)-1,3,3-trimethyl-2-oxabicyclo[2.2.2]oct-6-yl acetate Ref: 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; 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.

Ionones, Irones, Damascones & Structurally Related Odorants

Acyclics (Alcohols, Esters, Acids, Aldehydes)

Lactones

Sesquiterpenoid Related Odorants