The catecholic antioxidant piceatannol is an effective nitrosation inhibitor via an unusual double bond nitration

Piceatannol (1) was found to be more effective than caffeic acid, an established antinitrosating agent, in inhibiting N-nitrosation of 2,3-diaminonaphthalene. Product analysis of the reaction mixture of 1 (20 μM) with nitrite ions (80 μM) at pH 3.0 and at 37 °C showed conversion to a single major nitration product, (E)-3,3′,4,5′-tetrahydroxy-β-nitrostilbene (2) (68% yield). This would result from an unexpected nitration at the double bond sector via the 4-phenoxyl radical, which was analyzed at the unrestricted DFT level.