High-yielding synthesis of methyl orthoformate-protected hydroxytyrosol and its use in preparation of hydroxytyrosyl acetate.
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.
Gambacorta
Augusto
A
Dipartimento di Ingegneria Meccanica e Industriale, Università degli studi Roma Tre, via della Vasca Navale 79, 00146 Roma, Italy. gambacor@uniroma3.it
Tofani
Daniela
D
Migliorini
Antonella
A
D000085:Acetates / Q000138:chemical synthesis* / Q000737:chemistry; D052117:Benzodioxoles / Q000138:chemical synthesis* / Q000737:chemistry; D002396:Catechols / Q000138:chemical synthesis* / Q000737:chemistry; D010626:Phenylethyl Alcohol / Q000031:analogs & derivatives* / Q000737:chemistry
D000085:Acetates; D052117:Benzodioxoles; D002396:Catechols; C524604:hydroxytyrosyl acetate; C524605:hydroxytyrosyl methyl orthoformate; C005975:3,4-dihydroxyphenylethanol; D010626:Phenylethyl Alcohol