synthesis and olfactory evaluation of bulky moiety-modified analogues to the sandalwood odorant polysantol?合成和嗅觉评价笨重的檀香气味polysantol moiety-modified类似物.pdfVIP
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synthesis and olfactory evaluation of bulky moiety-modified analogues to the sandalwood odorant polysantol?合成和嗅觉评价笨重的檀香气味polysantol moiety-modified类似物
Molecules 2009, 14, 2780-2800; doi:10.3390/molecule
OPEN ACCESS
molecules
ISSN 1420-3049
/journal/molecules
Article
Synthesis and Olfactory Evaluation of Bulky Moiety-Modified
Analogues to the Sandalwood Odorant Polysantol®
Laura Chapado, Pablo J. Linares-Palomino, Concepción Badía, Sofía Salido, Manuel Nogueras,
Adolfo Sánchez and Joaquín Altarejos *
Departamento de Química Inorgánica y Orgánica, Facultad de Ciencias Experimentales, Universidad
de Jaén, 23071 Jaén, Spain
* Author to whom correspondence should be addressed; E-mail: jaltare@ujaen.es;
Tel. +34 953 212743; Fax: +34 953 211876
Received: 17 June 2009; in revised form: 21 July 2009 / Accepted: 27 July 2009 /
Published: 28 July 2009
Abstract: Five new bulky moiety-modified analogues of the sandalwood odorant
Polysantol® have been synthesized by aldol condensation of appropriate aldehydes with
butanone, deconjugative -methylation of the resulting -unsaturated ketones, and
reduction of the corresponding -unsaturated ketones. The final compounds were
evaluated organoleptically and one of them seemed to be of special interest for its natural
sandalwood scent.
Keywords: sandalwood odorants; Polysantol® analogues; nopol derivative; odour
evaluation
1. Introduction
(–)-(Z)-β-Santalol (1), the main constituent of natural sandalwood oil, is an odour compound with
typical sandalwood fragrance and is described as warm-woody, creamy and sweet
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