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

The Tetrahydroionols or

The 1-[2,2,6-trimethylcyclohexyl]butan-3-ols

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Photo by permission of M. Roudintska - Art & Parfum

(1R,6S)-(+)-tetrahydroionol - diffusive amber odor with slightly floral, orrisy and earthy note (Yamamoto et al.); also described as slightly floral and orris-lke amber fragrance (Ohmoto et al. for a 95: 5 % ratio of trans/cis isomers)

Odor Threshold = 400 ppb

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

= 1-[(1'R,6'S)-2',2',6'-trimethylcyclohexyl]butan-3-ol

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; Ohmoto, Tatsuya; Shimada, Akemi; Yamamoto, Takeshi; Propanol derivatives and perfumes containing the same, United States Patent RE37,159 May 1, 2001 & United States Patent 5,250,512, Oct. 5, 1993, Assigned to Takasago International Corp.

(1S,6R)-(-)-tetrahydroionol - faint vetiver-like woody odor (Yamamoto et al.); also described as a very faint woody odor (Ohmoto et al. for a 95: 5 % ratio of trans/cis isomers)

Odor Threshold = 1000 ppb

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

= 1-[(1'S,6'R)-2',2',6'-trimethylcyclohexyl]butan-3-ol

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; Ohmoto, Tatsuya; Shimada, Akemi; Yamamoto, Takeshi; Propanol derivatives and perfumes containing the same, United States Patent RE37,159 May 1, 2001 & United States Patent 5,250,512, Oct. 5, 1993, Assigned to Takasago International Corp.

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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