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

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

1
Agrobiology and Agrochemistry Department, University of Tuscia, Via S. Camillo De Lellis, 01100 Viterbo, Italy
2
Department of Chemical Sciences, University of Catania, Via A. Doria 6, I-95125 Catania, Italy
*
Author to whom correspondence should be addressed.
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 (CC BY 3.0).

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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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