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

The Isoborneols

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Photo by permission of M. Roudintska - Art & Parfum

(S)-(+)-isoborneol - camphoraceous, celluloid-like (Boelens et al.); Camphoraceous, India ink-like (odor evaluation by GC-olfactometry) (Nishimura)

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

Note on the absolute configuration - (1R,4R)-(+)-camphor produces mainly (1R,2R,4R)-(-)-isoborneol plus lesser amounts of (1R,2S,4R)-(+)-borneol on reduction with Lithium aluminium hydride; conversely (-)-isoborneol produces (+)-camphor on oxidation. As many textbooks have incorrectly stated reversed configurations for camphor, we are sure that both Boelens et al. and Nishimura et al. also assumed the incorrect configuration of (S)-(-)- and (1S,2S,4S)-(-)-isoborneol.

Ref: M. Guillot and R. Batin, CR Acad. Sci., 229(II) 1363-1365 (1949); Mans H. Boelens, Harrie Boelens & Leo J. van Gemert, Perfumer & Flavorist, Vol. 18, No. 6, 1-15, 1993; 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)

(R)-(-)-isoborneol - camphoraceous, sweet & musty (Boelens et al.); Camphoraceous, India ink-like (odor evaluation by GC-olfactometry) (Nishimura)

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

Note on the absolute configuration - (1R,4R)-(+)-camphor produces mainly (1R,2R,4R)-(-)-isoborneol plus lesser amounts of (1R,2S,4R)-(+)-borneol on reduction with Lithium aluminium hydride; conversely (-)-isoborneol produces (+)-camphor on oxidation. As many textbooks have incorrectly stated reversed configurations for camphor, we are sure that both Boelens et al. and Nishimura et al. also assumed the incorrect configuration of (S)-(-)- and (1S,2S,4S)-(-)-isoborneol.

Ref: M. Guillot and R. Batin, CR Acad. Sci., 229(II) 1363-1365 (1949); Mans H. Boelens, Harrie Boelens & Leo J. van Gemert, Perfumer & Flavorist, Vol. 18, No. 6, 1-15, 1993; 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)

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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