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

The Tetrahydroionols

You must have installed the Chime plugin to view the molecular visualization on Photo by permission of M. Roudintska - Art & Parfum

(1R,6S)-(+)-tetrahydroionol - diffusive amber odor with slightly floral, orrisy and earthy note

= (1'R,6'S)-(+)- 4-(2',2',6'-Trimethyl-cyclohexyl)-butan-2-ol

Odor Threshold = 400 ppb

Note that the C-3 position is epimeric, so this actually is a mixture of (1'R,3S,6'S) & (1'R,3R,6'S) isomers

Ref: Takeshi Yamamoto, Akemi Shimada, Tatsuya Ohmoto, Hiroyuki Matsuda, Miharu Ogura and Tsuneyoshi Kanisawa, Flavour and Fragrance Journal, Volume 19, Issue 2, Date: March/April 2004, Pages: 121-133; T. Yamamoto, H. Matsuda, T. Ohmoto, A. Shimada & T. Sato, Proc. 12th Int. Congress of Flavours, Fragrances & Essential oils, Vienna, Austria, Oct. 4-8, 1992, pp.442-455

(1S,6R)-(-)-tetrahydroionol - faint vetiver-like woody odor

= (1'S,6'R)-(-)- 4-(2',2',6'-Trimethyl-cyclohexyl)-butan-2-ol

Odor Threshold = 1000 ppb

Note that the C-3 position is epimeric, so this actually is a mixture of (1'S,3R,6'R) & (1'S,3S,6'R) isomers

Ref: Takeshi Yamamoto, Akemi Shimada, Tatsuya Ohmoto, Hiroyuki Matsuda, Miharu Ogura and Tsuneyoshi Kanisawa, Flavour and Fragrance Journal, Volume 19, Issue 2, Date: March/April 2004, Pages: 121-133; T. Yamamoto, H. Matsuda, T. Ohmoto, A. Shimada & T. Sato, Proc. 12th Int. Congress of Flavours, Fragrances & Essential oils, Vienna, Austria, Oct. 4-8, 1992, pp.442-455

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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