New lipophilic piceatannol derivatives exhibiting antioxidant activity prepared by aromatic hydroxylation with 2-iodoxybenzoic acid (IBX).
Piceatannol (E-3,5,3',4'-tetrahydroxystilbene) is a phytoalexin synthesized in grapes in response to stress conditions. It exhibits strong antioxidant and antileukaemic activities due to the presence of the catechol moiety. To modify some physical properties like solubility, and miscibility in non-aqueous media some new previously unreported piceatannol derivatives having lipophilic chains on the A-ring were prepared in good yields by a simple and efficient procedure. The key step was a chemo- and regioselective aromatic hydroxylation with 2-iodoxybenzoic acid (IBX). The new compounds showed antioxidant activity and seemed promising for possible applications as multifunctional emulsifiers in food, cosmetic and pharmaceutical fields.
Bernini
Roberta
R
Agrobiology and Agrochemistry Department, University of Tuscia, Viterbo, Italy. berninir@unitus.it
Barontini
Maurizio
M
Spatafora
Carmela
C
D000975:Antioxidants / Q000138:chemical synthesis* / Q000737:chemistry*; D007462:Iodobenzenes; D007463:Iodobenzoates / Q000737:chemistry*; D015394:Molecular Structure; D013267:Stilbenes / Q000138:chemical synthesis* / Q000737:chemistry*; D013329:Structure-Activity Relationship
D000975:Antioxidants; D007462:Iodobenzenes; D007463:Iodobenzoates; D013267:Stilbenes; C476101:o-iodoxybenzoic acid; C041525:3,3',4,5'-tetrahydroxystilbene