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Molecules 2009, 14(11), 4669-4681; doi:10.3390/molecules14114669
Article

New Lipophilic Piceatannol Derivatives Exhibiting Antioxidant Activity Prepared by Aromatic Hydroxylation with 2-Iodoxybenzoic Acid (IBX)

1,* , 1 and 2
Received: 2 October 2009 / Revised: 17 November 2009 / Accepted: 17 November 2009 / Published: 17 November 2009
(This article belongs to the Special Issue Organic Iodine Chemistry)
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Abstract

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.
Keywords: aromatic hydroxylation; 2-iodoxybenzoic acid (IBX); lipophilic piceatannol derivatives; lipophilic antioxidants aromatic hydroxylation; 2-iodoxybenzoic acid (IBX); lipophilic piceatannol derivatives; lipophilic antioxidants
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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Bernini, R.; Barontini, M.; Spatafora, C. New Lipophilic Piceatannol Derivatives Exhibiting Antioxidant Activity Prepared by Aromatic Hydroxylation with 2-Iodoxybenzoic Acid (IBX). Molecules 2009, 14, 4669-4681.

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