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

1,6-Dihydroionones

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Photo by permission of M. Roudintska - Art & Parfum

(1S,6S)-(+)-1,6-dihydroionone - very strong violet leaf odor like alpha-ionone (Yamamoto, et. al.); aromatic, carvone, woody, humus, powdery, ionone, myrrh, violet, strong (Chapuis & Brauchli)

Odor Threshold = 25 ppb

= (1'S,6'S)-(+)-4-(2',2',6'-Trimethyl-cyclohexyl)-but-3-en-2-one

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; Christian Chapuis & Robert Brauchli, Preparation of Optically Active Flowery and Woody-Like Odorant Ketones via Corey-Chaykovsky Oxiranylation: Irones and Analogues , Helv.Chim.Acta 1993, 76: 2070-2088

(1R,6R)-(-)-1,6-dihydroionone - weak woody odor with chemical note (Yamamoto, et. al.); woody, ionone, leather, camphor, weak (Chapuis & Brauchli)

Odor Threshold = 10 ppb

= (1'R,6'R)-(-)- 4-(2',2',6'-Trimethyl-cyclohexyl)-but-3-en-2-one

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; Christian Chapuis & Robert Brauchli, Preparation of Optically Active Flowery and Woody-Like Odorant Ketones via Corey-Chaykovsky Oxiranylation: Irones and Analogues , Helv.Chim.Acta 1993, 76: 2070-2088

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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