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-(1R,2S)-georgywood.gif)
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(-)-(1R,2S)-Georgywood®
= "Georgyone" - Woody-ambery; Bottom
note: Fresh, minty, green, sweet (Frater, et.
al.); Hong & Corey describe the odor as "an
intense clean woody odor".
Odor
threshold - 20 pg/L (Determined on the
sniff-outlet of a chiral GC-column with a panel
of three experienced fragrance chemists. The
authors were aware of the fact that the
separated enantiomers contained 4–6% of
their antipodes. This means, however, that the
factor of the odour threshold values is >175,
because
(+)-(1S,2R)-Georgywood®
is even weaker.
=
(-)-1-[(1R,2S)-1,2,8,8-tetramethyl-1,2,3,4,5,6,7,8-octahydronaphthalen-2-yl]ethanone
Ref:
Ref: Sungwoo Hong and E. J. Corey,
Enantioselective Syntheses of Georgyone,
Arborone, and Structural Relatives. Relevance to
the Molecular-Level Understanding of Olfaction,
J. Am. Chem. Soc., 2006; 128(4) pp 1346 - 1352;
Georg Frater, Urs Muller and Fridtjof Schroder,
Synthesis and olfactory properties of
(-)-(1R,2S)-Georgywood, Tetrahedron: Asymmetry,
15, 3967–3972 (2004)
An outline of
Hong & Corey's synthesis can be found
HERE.
Georgywood®
is a trademark
of Givaudan SA
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-(1s,2r)-georgywood.gif)
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(+)-(1S,2R)-Georgywood®
= ent-Georgyone - Weakly woody; Bottom note:
musty (Frater, et. al.); Hong & Corey found
this enantiomer to possess a relatively weak
odor which is best described as distinctly
unpleasant-acrid-musty.
Odor
threshold - 3.5 ng/L (Determined on the
sniff-outlet of a chiral GC-column with a panel
of three experienced fragrance
chemists.
=
(+)-1-[(1S,2R)-1,2,8,8-tetramethyl-1,2,3,4,5,6,7,8-octahydronaphthalen-2-yl]ethanone
Ref:
Ref: Sungwoo Hong and E. J. Corey,
Enantioselective Syntheses of Georgyone,
Arborone, and Structural Relatives. Relevance to
the Molecular-Level Understanding of Olfaction,
J. Am. Chem. Soc., 2006; 128(4) pp 1346 - 1352;
Georg Frater, Urs Muller and Fridtjof Schroder,
Synthesis and olfactory properties of
(-)-(1R,2S)-Georgywood, Tetrahedron: Asymmetry,
15, 3967–3972 (2004)
An outline of
Hong & Corey's synthesis can be found
HERE.
Georgywood®
is a trademark
of Givaudan SA
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