High-Yielding Synthesis of Methyl Orthoformate-Protected Hydroxytyrosol and Its Use in Preparation of Hydroxytyrosyl Acetate
| Autor: | A. Gambacorta, Antonella Migliorini, Daniela Tofani |
|---|---|
| Přispěvatelé: | Gambacorta, Augusto, Tofani, Daniela, Antonella, Migliorini, Augusto, Gambacorta |
| Jazyk: | angličtina |
| Rok vydání: | 2007 |
| Předmět: |
Antioxidant
antioxidant medicine.medical_treatment Catechols Pharmaceutical Science Acetates High yielding Hydroxytyrosyl acetate Analytical Chemistry lcsh:QD241-441 Hydrolysis chemistry.chemical_compound lcsh:Organic chemistry Drug Discovery medicine Organic chemistry Hydroxytyrosol Benzodioxoles Physical and Theoretical Chemistry protective groups Ethanol Full Paper Active principle Organic Chemistry hydroxytyrosyl ester Phenylethyl Alcohol antioxidants chemistry Chemistry (miscellaneous) Molecular Medicine hydroxytyrosyl esters hydroxytyrosol |
| Zdroj: | Molecules, Vol 12, Iss 8, Pp 1762-1770 (2007) Molecules Volume 12 Issue 8 Pages 1762-1770 |
| ISSN: | 1420-3049 |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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