Molecules 2007, 12(8), 1762-1770; doi:10.3390/12081762
Article

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

Augusto Gambacorta 1,* email, Daniela Tofani 1,* email and Antonella Migliorini 2
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.
Received: 30 May 2007; in revised form: 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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Abstract: 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.
Keywords: Hydroxytyrosol; antioxidants; hydroxytyrosyl esters; protective groups.

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MDPI and ACS Style

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.

AMA Style

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(8):1762-1770.

Chicago/Turabian Style

Gambacorta, Augusto; Tofani, Daniela; Migliorini, Antonella. 2007. "High-Yielding Synthesis of Methyl Orthoformate-Protected Hydroxytyrosol and Its Use in Preparation of Hydroxytyrosyl Acetate." Molecules 12, no. 8: 1762-1770.

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