(1S,2S,4R)-(+)-2-Hydroxy-1,8-cineole - Cineole-like, sweet odor (Miyazawa and Hashimoto); Also described as Citrus (2), sweet (1), grape juice (1), eucalyptus (1) as evaluated by 6 panelists by GC-O (Kirsch and Buettner)  Also called (1S,4R,6S)-6-Hydroxy-1,8-cineole = (1S,2S,4R)-1,5,5-trimethyl-6-oxa-bicyclo[2.2.2]octan-2-ol = (1S,4R,6S)-1,3,3-trimethyl-2-oxabicyclo[2.2.2]octan-6-ol Ref: Miyazawa, Mitsuo, and Yuya Hashimoto. "Microbial resolution of racemic 2-endo-acetoxy-1,8-cineole by Glomerella cingulata." Tetrahedron: Asymmetry 12, no. 22 (2001): 3185-3187; Kirsch, Frauke, and Andrea Buettner. "Odor Qualities and Thresholds of Physiological Metabolites of 1,8-Cineole as an Example for Structure Activity Relationships Considering Chirality Aspects." Chemistry & biodiversity 10, no. 9 (2013): 1683-1695. See MacRae, Ian C., V. Alberts, R. M. Carman, and I. M. Shaw. "Products of 1, 8-cineole oxidation by a pseudomonad." Australian Journal of Chemistry 32, no. 4 (1979): 917-922 for determination of the absolute configurations.

(1R,2R,4S)-(-)-2-Hydroxy-1,8-cineole - Camphorous odor (Miyazawa and Hashimoto); Also described as Eucalyptus (5), pine needle (4), fresh/pungent (3), citrus (2), cleanser (2), soapy (1), flowery (1), sweet (1) as evaluated by 6 panelists by GC-O (Kirsch and Buettner) Also called (1R,4S,6R)-6-Hydroxy-1,8-cineole = (1R,2R,4S)-1,5,5-trimethyl-6-oxa-bicyclo[2.2.2]octan-2-ol = (1R,4S,6R)-1,3,3-trimethyl-2-oxabicyclo[2.2.2]octan-6-ol Ref: Miyazawa, Mitsuo, and Yuya Hashimoto. "Microbial resolution of racemic 2-endo-acetoxy-1,8-cineole by Glomerella cingulata." Tetrahedron: Asymmetry 12, no. 22 (2001): 3185-3187; Kirsch, Frauke, and Andrea Buettner. "Odor Qualities and Thresholds of Physiological Metabolites of 1,8-Cineole as an Example for Structure Activity Relationships Considering Chirality Aspects." Chemistry & biodiversity 10, no. 9 (2013): 1683-1695. See MacRae, Ian C., V. Alberts, R. M. Carman, and I. M. Shaw. "Products of 1, 8-cineole oxidation by a pseudomonad." Australian Journal of Chemistry 32, no. 4 (1979): 917-922 for determination of the absolute configurations.

(1S,2R,4R)-(-)-2-Hydroxy-1,8-cineole - Eucalyptus (4), pine needle (3), faecal (2), earthy (1), plastic (1) as evaluated by 5 panelists by GC-O (Kirsch and Buettner) Also called (1S,4R,6R)-6-Hydroxy-1,8-cineole = (1S,2R,4R)-1,5,5-trimethyl-6-oxa-bicyclo[2.2.2]octan-2-ol = (1S,4R,6R)-1,3,3-trimethyl-2-oxabicyclo[2.2.2]octan-6-ol Ref: Kirsch, Frauke, and Andrea Buettner. "Odor Qualities and Thresholds of Physiological Metabolites of 1,8-Cineole as an Example for Structure Activity Relationships Considering Chirality Aspects." Chemistry & biodiversity 10, no. 9 (2013): 1683-1695. Note - the absolute configurations assigned by Kirsch and Buettner need validation.

Ionones, Irones, Damascones & Structurally Related Odorants

Acyclics (Alcohols, Esters, Acids, Aldehydes)

Lactones

Sesquiterpenoid Related Odorants