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.pdf

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