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

The Dihydro-Irones

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Photo by permission of M. Roudintska - Art & Parfum

(1'R,3'R,6'R)-(E)-(-)-dihydroirone - Woody, powdery, incense.

The description given for racemate is: iris-violet note, powdery, balsamic, reminiscent of myrrh, woody, exceptional strength and tenacity odor

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

Ref: Chapuis;Christian; Schulte-Elte; Karl-Heinrich; Pamingle; Herve; Margot; Christian, United States Patent 5,118,865, June 2, 1992; 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; Elisabetta Brenna, Claudio Fuganti and Stefano Serra, Enantioselective perception of chiral odorants, Tetrahedron: Asymmetry, 14, 1–42 (2003)

(1'S,3'S,6'S)-(E)-(+)-dihydroirone - iris-irone note with a very warm balsamic-myrrh, woody character. The violet-iris character is more pronounced than in (1'R,3'R,6'R)-(E)-(-)-enantiomer or the racemate and the odor note is even stronger

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

Ref: Chapuis;Christian; Schulte-Elte; Karl-Heinrich; Pamingle; Herve; Margot; Christian, United States Patent 5,118,865, June 2, 1992; 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; Elisabetta Brenna, Claudio Fuganti and Stefano Serra, Enantioselective perception of chiral odorants, Tetrahedron: Asymmetry, 14, 1–42 (2003)

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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