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

The gamma-Irones

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Photo by permission of M. Roudintska - Art & Parfum

(1S,5R)-(+)-cis-gamma-irone - iris, sweet, woody ionone, dry floral (Galfry, et.al, by GC sniffing); Inoue, et. al., indicate the (-)-cis-gamma-irone fragrance is Floral, green; weak; Brenna, et. al. describe it as showing a floral, fatty, sweet, and woody odour character, an ionone-type odour with slightly sweet aspects

Odor threshold = 100 ng/l (0.1 ppb)

also known as (2R,6S)-(+)-cis-gamma-irone

Ref: A. Galfry, P. Martin and M. Petrizilka, J. Essent. Oil Res., 5, 265-277 (1993); T. Inoue, H. Kiyota & T. Oritani, Synthesis of both enantiomers of cis-a-irone and cis-g-irone,principal constituents of iris oil, via resolution of (±)-2,2,4-trimethyl-3-cyclohexene-1-carboxylic acid Tetrahedron: Assymetry, 11(18), 3807-3818 (2000); 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, 2001, 84(1), 69-86; Brenna, Elisabetta; Fuganti, Claudio; Ronzani, Sabrina; Serra, Stefano, Enzyme-Mediated Syntheses of the Enantiomers of gamma-Irones, Helv. Chim. Acta, 84(12), 3650-3666 (2001); Elisabetta Brenna, Claudio Fuganti and Stefano Serra, Enantioselective perception of chiral odorants, Tetrahedron: Asymmetry, 14, 1–42 (2003)

(1R,5S)-(-)-cis-gamma-irone - odourless (Galfry, et. al.); In contrast, Inoue, et. al., indicate the (-)-cis-gamma-irone fragrance is superior to its enantiomer with Floral, sweet, ionone-like notes; Brenna, et. al. describe it as showing a "beta-ionone-type odour of warm floral-woody tonality. Green aspects are present, too. It shows some fruity nuances, reminiscent of pineapples. The odour is linear, and it can be considered a dry-down note"

Odor threshold = 0.75 ng/l (0.00075 ppb)

also known as (2S,6R)-(-)-cis-gamma-irone

Ref: A. Galfry, P. Martin and M. Petrizilka, J. Essent. Oil Res., 5, 265-277 (1993); T. Inoue, H. Kiyota & T. Oritani, Synthesis of both enantiomers of cis-a-irone and cis-g-irone,principal constituents of iris oil, via resolution of (±)-2,2,4-trimethyl-3-cyclohexene-1-carboxylic acid Tetrahedron: Assymetry, 11(18), 3807-3818 (2000); 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, 2001, 84(1), 69-86; Brenna, Elisabetta; Fuganti, Claudio; Ronzani, Sabrina; Serra, Stefano, Enzyme-Mediated Syntheses of the Enantiomers of gamma-Irones, Helv. Chim. Acta, 84(12), 3650-3666 (2001); Elisabetta Brenna, Claudio Fuganti and Stefano Serra, Enantioselective perception of chiral odorants, Tetrahedron: Asymmetry, 14, 1–42 (2003)

(1S,5S)-(-)-trans-gamma-irone - iris and floral note, ionone, like trans-alpha-irone (Galfry, et.al, by GC sniffing); Brenna, et. al. describe it as not very powerful, but it possesses a soft ‘orris-butter’-type of odour

Odor threshold = 26.35 ng/l (0.02635 ppb)

also known as (2S,6S)-(-)-trans-gamma-irone

Ref: A. Galfry, P. Martin and M. Petrizilka, J. Essent. Oil Res., 5, 265-277 (1993); Brenna, Elisabetta; Fuganti, Claudio; Ronzani, Sabrina; Serra, Stefano, Enzyme-Mediated Syntheses of the Enantiomers of gamma-Irones, Helv. Chim. Acta, 84(12), 3650-3666 (2001); Elisabetta Brenna, Claudio Fuganti and Stefano Serra, Enantioselective perception of chiral odorants, Tetrahedron: Asymmetry, 14, 1–42 (2003)

(1R,5R)-(+)-trans-gamma-irone - weak, burnt smell, metallic, chemical (Galfry, et.al, by GC sniffing); Brenna, et. al. describe it as very weak, of a woody odour tonality

Odor threshold = 113.5 ng/l (0.1135 ppb)

also known as (2R,6R)-(+)-trans-gamma-irone

Ref: A. Galfry, P. Martin and M. Petrizilka, J. Essent. Oil Res., 5, 265-277 (1993); Brenna, Elisabetta; Fuganti, Claudio; Ronzani, Sabrina; Serra, Stefano, Enzyme-Mediated Syntheses of the Enantiomers of gamma-Irones, Helv. Chim. Acta, 84(12), 3650-3666 (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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