Chirality & Odour Perception
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

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Photo by permission of M. Roudintska - Art & Parfum

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(-)-2-Methyl-2-(3-methylbenzyl)but-3-en-1-ol - described as a flowery, but more Majantol like and showed no Linalool like fragrance

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 4343–4346 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

c

 

(+)-2-Methyl-2-(3-methylbenzyl)but-3-en-1-ol - strong floral and linalool-like - With a very weak Majantol-like character - and was perceived as much more intense than that of the (-)-antipode

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 4343–4346 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 - 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 4343–4346 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 4343–4346 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

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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