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

The beta-Irones

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Photo by permission of M. Roudintska - Art & Parfum

(2R)-(+)-beta-irone - iris family, anis, liquorice, green (Galfry, et.al, by GC sniffing); Brenna, et. al. describe it as possessing a beta-ionone-type odour of warm floral-woody tonality with green and anisic aspects. The odour is linear, and the tenacity of the note is good. It can be considered a dry-down note

Also known as (5R)-(+)-beta-irone

Ref: A. Galfry, P. Martin and M. Petrizilka, J. Essent. Oil Res., 5, 265-277 (1993); Brenna, Elisabetta; Delmonte, Marco; Fuganti, Claudio; Serra, Stefano, Enzyme-Mediated Preparation of (+)- and (-)-ß-Irone and (+)- and (-)-cis-gamma-Irone from Irone alpha, Helv. Chim. Acta, 84(1), 69-86 (2001); Elisabetta Brenna, Claudio Fuganti and Stefano Serra, Enantioselective perception of chiral odorants, Tetrahedron: Asymmetry, 14, 1–42 (2003)

(2S)-(-)-beta-irone - poor, weakly iris (Galfry, et.al, by GC sniffing); Brenna, et. al. describe it as having a woody odour with a distinct honey note, that is quite sweet. Besides, it shows floral ionone-type facets, and a fruity tonality, but also an unpleasant smoky character. It belongs to the beta-ionone-type family, without being very close to beta-ionone

Also known as (5S)-(-)-beta-irone

Ref: A. Galfry, P. Martin and M. Petrizilka, J. Essent. Oil Res., 5, 265-277 (1993); Brenna, Elisabetta; Delmonte, Marco; Fuganti, Claudio; Serra, Stefano, Enzyme-Mediated Preparation of (+)- and (-)-ß-Irone and (+)- and (-)-cis-gamma-Irone from Irone alpha, Helv. Chim. Acta, 84(1), 69-86 (2001); 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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Copyright 2001 - Leffingwell & Associates