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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

1,* , 1,*  and 2
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. Hydroxytyrosol; antioxidants; hydroxytyrosyl esters; protective groups.
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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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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