A Convenient Synthesis of Hydroxytyrosol Monosulfate Metabolites.
The growing interest in the bioactivity of natural polyphenols and of their metabolites requires metabolites to be used in bioassays and as standards in research protocols. We report here on the synthesis of several hydroxytyrosol metabolite monosulfates achieved using a simplified protocol with improved yields. A synthetic solution based on avoidance of high temperature conditions during the synthesis and of low pressure conditions during purification has been established. Monosulfates of several phenolic compounds, namely, hydroxytyrosol, hydroxytyrosol acetate, homovanillyl alcohol, homovanillyl alcohol acetate, homovanillic acid, ferulic acid, and 3,4-dihydroxyphenylethanoic acid, were efficiently synthesized in 1-2 steps in good yield and isolated using simple procedures. The proposed protocol was shown to be relatively rapid, efficient, cheap, and widely applicable to a number of catechol scaffolds.
REQUIMTE, Faculdade de Ciências, Universidade do Porto , Rua do Campo Alegre, 687, 4169-007 Porto, Portugal.
Vânia Patrícia Martins
VP
Gomes
REQUIMTE, Faculdade de Ciências, Universidade do Porto , Rua do Campo Alegre, 687, 4169-007 Porto, Portugal.
Carmen
C
Torres
REQUIMTE, Faculdade de Ciências, Universidade do Porto , Rua do Campo Alegre, 687, 4169-007 Porto, Portugal.
José Enrique
JE
Rodríguez-Borges
REQUIMTE, Faculdade de Ciências, Universidade do Porto , Rua do Campo Alegre, 687, 4169-007 Porto, Portugal.
Fátima
F
Paiva-Martins
D060326:Chemistry Techniques, Synthetic / Q000379:methods*; D015394:Molecular Structure; D010626:Phenylethyl Alcohol / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000378:metabolism; D059808:Polyphenols / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism; D013431:Sulfates / Q000737:chemistry* / Q000378:metabolism
D059808:Polyphenols; D013431:Sulfates; C005975:3,4-dihydroxyphenylethanol; D010626:Phenylethyl Alcohol
homovanillyl alcohol; hydroxytyrosol; hydroxytyrosol acetate; metabolites; olive oil; polyphenols; sulfates