Synthesis, olfactory evaluation and determination of the absolute configuration of the β- and γ-Iralia® isomers

Abstract

The regioselective synthesis of the methyl-ionone isomers 6-9 is described. The enantiomers of the ??-isomers 8 and 9 are prepared by enzyme-mediated resolution of the corresponding 4-hydroxy derivatives followed by reductive elimination of the hydroxy group. The absolute configuration of the latter compound is determined by chemical correlation with the known ??-isomers. Since all the isomers obtained are components of the artificial violet odourants sold under the trade name of Iralia??, their odour properties are evaluated by professional perfumers. ?? 2008 Elsevier Ltd. All rights reserved.