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High-Yielding Synthesis of Methyl Orthoformate-Protected Hydroxytyrosol and Its Use in Preparation of Hydroxytyrosyl Acetate

Dipartimento di Ingegneria Meccanica e Industriale, Università degli studi “Roma Tre”, via della Vasca Navale 79, 00146 Roma, Italy
Dipartimento di Chimica, Università “La Sapienza”, P.le Aldo Moro 5, 00185 Rome, Italy
Authors to whom correspondence should be addressed.
Molecules 2007, 12(8), 1762-1770;
Received: 30 May 2007 / Revised: 31 July 2006 / Accepted: 1 August 2007 / Published: 8 August 2007
(This article belongs to the Special Issue Phenolics and Polyphenolics)
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The new methyl orthoformate of the powerful antioxidant hydroxytyrosol (or 2- (3,4-dihydroxyphenyl)ethanol) 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.

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Gambacorta, A.; Tofani, D.; Migliorini, A. High-Yielding Synthesis of Methyl Orthoformate-Protected Hydroxytyrosol and Its Use in Preparation of Hydroxytyrosyl Acetate. Molecules 2007, 12, 1762-1770.

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