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

The Citronellols

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Photo by permission of M. Roudintska - Art & Parfum

(3R)-(+)-citronellol - citronella oil-like

Described by Yamamoto et.al., as slightly oily light rosy-leafy, petal like odor with irritating topnote

Also described as Difusive rosy odor close to laevocitronellol with the odor aspects of Bulgarian rose and lily of the valley by Asao et al.

Ref: R. Rienaecker and G. Ohloff, Angew. Chem. 73, 240 (1961); Mans H. Boelens, Harrie Boelens & Leo J. van Gemert, Perfumer & Flavorist, Vol. 18, No. 6, 1-15, 1993; 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; Hiroki Asao, Hiroyuki Sakauchi, Shigefumi Kuwahara and Hiromasa Kiyota, Synthesis and odor description of optically active cyclopropanated analogues of geraniol, nerol, nor-leaf alcohol, and matsutake alcohol, Tetrahedron: Asymmetry, 18 (2007) 537–541

(3S)-(-)-citronellol - floral, rose-like odor, reminiscent of geranium oil

Described by Yamamoto et.al. as very fresh light and clean rosy-leafy, petal-like

Also described as Somewhat citronellal-like odor with woody aspect, less intensive than the racemate and the (R)-enantiomer by Asao et al.

Ref: R. Rienaecker and G. Ohloff, Angew. Chem. 73, 240 (1961); Mans H. Boelens, Harrie Boelens & Leo J. van Gemert, Perfumer & Flavorist, Vol. 18, No. 6, 1-15, 1993; 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

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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