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• W2051219743 abstract "Oxidation of the natural antioxidant hydroxytyrosol (1) with peroxidase/H2O2 in phosphate buffer at pH 7.4 led to the formation of two main ethyl acetate-extractable products. These could be isolated by preparative TLC after reduction and acetylation, and were identified as the tetraacetyl derivative of 2-(2,4,5-trihydroxyphenyl)ethanol (3) and the heptaacetyl derivative of the pentahydroxybiphenyl 4 by 2D NMR and MS analysis. Similar oxidation of 4-methylcatechol gave, after the same work-up, the acetylated derivatives of 1,2,4-trihydroxy-5-methylbenzene (5) and the pentahydroxybiphenyl 6. Mechanistic experiments suggested that hydrogen peroxide affects the course of the oxidation of 1 by adding to the first formed o-quinone to give a hydroxyquinone intermediate. This could bring nucleophilic attack to the o-quinone of 1 to give the dimer 4. These results disclose novel oxidative pathways of 4-alkylcatechols and provide an improved chemical basis to enquire into the mechanism of the antioxidant action of 1." @default.
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• W2051219743 date "2006-02-01" @default.
• W2051219743 modified "2023-09-27" @default.
• W2051219743 title "Oxidative chemistry of the natural antioxidant hydroxytyrosol: hydrogen peroxide-dependent hydroxylation and hydroxyquinone/o-quinone coupling pathways" @default.
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• W2051219743 doi "https://doi.org/10.1016/j.tet.2005.10.055" @default.
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