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

The cis-Linalool Oxides (pyranoid)

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Photo by permission of M. Roudintska - Art & Parfum

(3R,6R)-cis-linalool oxide (pyranoid) - earthy

= (3R,6R)-2,2,6-trimethyl-6-vinyltetrahydro-2H-pyran-3-ol

In Wang et al., this enantiomer is referred to as the (2R,5R)- form.

Ref: G. Wang, D.; Ando, K.; Morita, K.; Kubota, K.; Kobayashi, A., Optical isomer of linalool and linalool oxides in tea aroma, Biosci. Biotechnol. Biochem. 1994, 58 (11), 2050-2053; Identification of Potent Odorants in Chinese Jasmine Green Tea Scented with Flowers of Jasminum sambac, YURIKO ITO, AKIO SUGIMOTO, TAKAMI KAKUDA, AND KIKUE KUBOTA, J. Agric. Food Chem. 2002, 50, 4878-4884

(3S,6S)-cis-linalool oxide (pyranoid) - sweet, floral, creamy

= (3S,6S)-2,2,6-trimethyl-6-vinyltetrahydro-2H-pyran-3-ol

In Wang et al., this enantiomer is referred to as the (2S,5S)- form.

Ref: G. Wang, D.; Ando, K.; Morita, K.; Kubota, K.; Kobayashi, A., Optical isomer of linalool and linalool oxides in tea aroma, Biosci. Biotechnol. Biochem. 1994, 58 (11), 2050-2053; Identification of Potent Odorants in Chinese Jasmine Green Tea Scented with Flowers of Jasminum sambac, YURIKO ITO, AKIO SUGIMOTO, TAKAMI KAKUDA, AND KIKUE KUBOTA, J. Agric. Food Chem. 2002, 50, 4878-4884

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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