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

Ethyl tetrahydrosafranates

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Photo by permission of M. Roudintska - Art & Parfum

(1R,6S)-(+)-ethyl tetrahydrosafranate - clean and sweet floral odor

Odor Threshold = 20 ppb

Described in United States Patent 5,288,702 as having strong diffusibility and a specific floral and fruit-like odor with high preference.

Also known as (+)-Ethyl (1R,6S)-2,2,6-trimethylcyclohexane-carboxylate

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; Miharu Ogura, Hiroyuki Matsuda, Takeshi Yamamoto, and Akemi Shimada; Ethyl (1R,6S)-2,2,6-trimethylcyclohexanecarboxylate, aroma chemical composition containing the same and process of producing the same, United States Patent 5,288,702 (February 22, 1994); Takeshi Yamamoto, , Hideo Ujihara, Shinya Watanabe, Makoto Harada, Hiroyuki Matsuda and Toshimitsu Hagiwara, Synthesis and odor of optically active trans-2,2,6-trimethylcyclohexyl methyl ketones and their related compounds, Tetrahedron, Volume 59, Issue 4 , 20 January 2003, Pages 517-524

(1S,6R)-(-)-ethyl tetrahydrosafranate - dirty and heavy fatty floral odor

Odor Threshold = 100 ppb

Described in United States Patent 5,288,702 as having about 1/3 of the odor intensity and fails in the diffusibility and feature of the specific fruit-like odor of the (1R,6S)-form

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; Miharu Ogura, Hiroyuki Matsuda, Takeshi Yamamoto, and Akemi Shimada; Ethyl (1R,6S)-2,2,6-trimethylcyclohexanecarboxylate, aroma chemical composition containing the same and process of producing the same, United States Patent 5,288,702 (February 22, 1994); Takeshi Yamamoto, , Hideo Ujihara, Shinya Watanabe, Makoto Harada, Hiroyuki Matsuda and Toshimitsu Hagiwara, Synthesis and odor of optically active trans-2,2,6-trimethylcyclohexyl methyl ketones and their related compounds, Tetrahedron, Volume 59, Issue 4 , 20 January 2003, Pages 517-524

 

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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