John C. Leffingwell, Ph.D. Chiral Analogs of Majantol The 2-Methyl-2-(3-methylbenzyl)but-3-en-1-ols & (Hydroxymethyl)methyl(3-methylbenzyl)vinylsilanes You must have
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(-)-(Hydroxymethyl)methyl(3-methylbenzyl)vinylsilane
- lacked the mushroom note of the (+)-antipode,
and instead had a very weak rosy muguet-like
odor Ref: Thomas
Schmid, Darstellung von Sila-Analoga und
siliciumhaltigen Derivaten von Wirk- und
Riechstoffen sowie alpha-Aminosauren im Rahmen von
Untersuchungen zur C/Si-Bioisosterie. PhD Thesis,
Bayerischen Julius-Maximilians-Universität
Würzburg, 2004; See also Thomas Schmid,
Jürgen O. Daiss, Rainer Ilg, Horst Surburg,
and Reinhold Tacke, Enantiopure Chiral Derivatives
of the Fragrance Materials Majantol and
Sila-majantol: A Bioisosteric Carbon/Silicon
Switch with Drastic Effects on the Sensory
Characteristics, Organometallics, 2003, 22 (21), pp
43434346 and I. Doszczak, T. Gaspari, A.
Saint-Dizier, M. A. Loreto and D. Enders,
Silylating Reagents: A powerful Tool for the
Construction of Isosteric Analogs of Highly
Branched Odorants in Perspectives in flavor and
fragrance research, Philip Kraft, Karl A. D. Swift,
Eds. Wiley-VCH, 2005, p 92 |
(+)-(Hydroxymethyl)methyl(3-methylbenzyl)vinylsilane
- not floral at all, but it had a mushroom note
and some muffy nuances; recalling the smell of many
species of fungi containing (R)-1-octene-3-ol and
also showed musty and earthy nuances Ref: Thomas
Schmid, Darstellung von Sila-Analoga und
siliciumhaltigen Derivaten von Wirk- und
Riechstoffen sowie alpha-Aminosauren im Rahmen von
Untersuchungen zur C/Si-Bioisosterie. PhD Thesis,
Bayerischen Julius-Maximilians-Universität
Würzburg, 2004; See also Thomas Schmid,
Jürgen O. Daiss, Rainer Ilg, Horst Surburg,
and Reinhold Tacke, Enantiopure Chiral Derivatives
of the Fragrance Materials Majantol and
Sila-majantol: A Bioisosteric Carbon/Silicon
Switch with Drastic Effects on the Sensory
Characteristics, Organometallics, 2003, 22 (21), pp
43434346 and I. Doszczak, T. Gaspari, A.
Saint-Dizier, M. A. Loreto and D. Enders,
Silylating Reagents: A powerful Tool for the
Construction of Isosteric Analogs of Highly
Branched Odorants in Perspectives in flavor and
fragrance research, Philip Kraft, Karl A. D. Swift,
Eds. Wiley-VCH, 2005, p 92 |
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Ionones, Irones, Damascones & Structurally Related Odorants |
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