A Convenient Synthesis of Hydroxytyrosol Monosulfate Metabolites

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• 作者：V芒nia Patr铆cia Martins Gomes ; Carmen Torres ; Jos茅 Enrique Rodr铆guez-Borges ; F谩tima Paiva-Martins
• 刊名：Journal of Agricultural and Food Chemistry
• 出版年：2015
• 出版时间：November 4, 2015
• 年：2015
• 卷：63
• 期：43
• 页码：9565-9571
• 全文大小：363K
• ISSN：1520-5118

文摘

The growing interest in the bioactivity of natural polyphenols and of their metabolites requires metabolites to be used in bioassays and as standards in research protocols. We report here on the synthesis of several hydroxytyrosol metabolite monosulfates achieved using a simplified protocol with improved yields. A synthetic solution based on avoidance of high temperature conditions during the synthesis and of low pressure conditions during purification has been established. Monosulfates of several phenolic compounds, namely, hydroxytyrosol, hydroxytyrosol acetate, homovanillyl alcohol, homovanillyl alcohol acetate, homovanillic acid, ferulic acid, and 3,4-dihydroxyphenylethanoic acid, were efficiently synthesized in 1鈥? steps in good yield and isolated using simple procedures. The proposed protocol was shown to be relatively rapid, efficient, cheap, and widely applicable to a number of catechol scaffolds.