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

The Borneols

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Photo by permission of M. Roudintska - Art & Parfum

(1S,2R,4S)-(-)-borneol - camphoraceous, India ink like (odor evaluation by GC-olfactometry) (Nishimura); (-)-Borneol has a camphoraceous and evident woody odor (Tabanca et al. & Jogdeo)

Odor Threshold = 80 ppb in water (Padrayuttawat et al.)

= (-)-(1S,2R,4S)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ol

Ref: Osamu Nishimura, Enantiomer separation of the characteristic odorants in Japanese fresh rhizomes of Zingiber officinale Roscoe (ginger) using multidimensional GC system and confirmation of the odour character of each enantiomer by GC-olfactometry, Flavour & Fragrance Journal, 16, 13-18 (2001); Nurhayat Tabanca, Nese Kirimer, Betul Demirci, Fatih Demirci, and K. Husnu Can Baser, Composition and Antimicrobial Activity of the Essential Oils of Micromeria cristata subsp. phrygia and the Enantiomeric Distribution of Borneol, J. Agric. Food Chem. 2001, 49, 4300-4303; Jogdeo, D. Optical Isomers in Perfumery and their Purification. Fafai J. 1999, 39-46; PADRAYUTTAWAT, A., T. YOSHIZAWA, H. TAMURA & T. TOKUNAGA (1997), Optical isomers and odor thresholds of volatile constituents in Citrus sudachi, Food Sci. Technol. Int. Tokyo, 3, 402-408

(1R,2S,4R)-(+)-borneol - camphoraceous, India ink like, slight fatty-putrid (odor evaluation by GC-olfactometry) (Nishimura); The (+) form has a camphoraceous odor and a slightly sharp, earthy-peppery note different from that of the (-) form (Tabanca et al.).

Odor Threshold = 80 ppb in water (Padrayuttawat et al.)

= (+)-(1R,2S,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ol

Ref: Osamu Nishimura, Enantiomer separation of the characteristic odorants in Japanese fresh rhizomes of Zingiber officinale Roscoe (ginger) using multidimensional GC system and confirmation of the odour character of each enantiomer by GC-olfactometry, Flavour & Fragrance Journal, 16, 13-18 (2001); Nurhayat Tabanca, Nese Kirimer, Betul Demirci, Fatih Demirci, and K. Husnu Can Baser, Composition and Antimicrobial Activity of the Essential Oils of Micromeria cristata subsp. phrygia and the Enantiomeric Distribution of Borneol, J. Agric. Food Chem. 2001, 49, 4300-4303; PADRAYUTTAWAT, A., T. YOSHIZAWA, H. TAMURA & T. TOKUNAGA (1997), Optical isomers and odor thresholds of volatile constituents in Citrus sudachi, Food Sci. Technol. Int. Tokyo, 3, 402-408

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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