(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)
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(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)
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