High-Yielding Synthesis of Methyl Orthoformate-Protected Hydroxytyrosol and Its Use in Preparation of Hydroxytyrosyl AcetateReportar como inadecuado




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1

Dipartimento di Ingegneria Meccanica e Industriale, Università degli studi -Roma Tre-, via della Vasca Navale 79, 00146 Roma, Italy

2

Dipartimento di Chimica, Università -La Sapienza-, P.le Aldo Moro 5, 00185 Rome, Italy





*

Authors to whom correspondence should be addressed.



Abstract The new methyl orthoformate of the powerful antioxidant hydroxytyrosol or 2- 3,4-dihydroxyphenylethanol has been synthesized by a two-step high yielding procedure. The protection stabilizes hydroxytyrosol against fast oxidation and allows both easy chromatographic purification and long term storage. The protective group is hydrolyzed over pH = 10 and below pH = 5, thus allowing the release of the active principle under physiological conditions. The use of the methyl orthoformate-protected hydroxytyrosol allows the preparation of protected hydroxytyrosyl esters, like the acetate herein reported, by selective esterification of the alcoholic function. The subsequent quantitative deprotection under non-aqueous and mild conditions affords the hydroxytyrosyl acetate in high yields. View Full-Text

Keywords: Hydroxytyrosol; antioxidants; hydroxytyrosyl esters; protective groups. Hydroxytyrosol; antioxidants; hydroxytyrosyl esters; protective groups.





Autor: Augusto Gambacorta 1,* , Daniela Tofani 1,* and Antonella Migliorini 2

Fuente: http://mdpi.com/



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