Efficient scavenging of β-carotene radical cations by antiinflammatory salicylates

Food & Function Pub Date: 2013-12-12 DOI: 10.1039/C3FO60519A

Abstract

The radical cation generated during photobleaching of β-carotene is scavenged efficiently by the anion of methyl salicylate from wintergreen oil in a second-order reaction approaching the diffusion limit with k2 = 3.2 × 109 L mol?1 s?1 in 9?:?1 v/v chloroform–methanol at 23 °C, less efficiently by the anion of salicylic acid with 2.2 × 108 L mol?1 s?1, but still of possible importance for light-exposed tissue. Surprisingly, acetylsalicylate, the aspirin anion, reacts with an intermediate rate in a reaction assigned to the anion of the mixed acetic–salicylic acid anhydride formed through base induced rearrangements. The relative scavenging rate of the β-carotene radical cation by the three salicylates is supported by DFT-calculations.

Graphical abstract: Efficient scavenging of β-carotene radical cations by antiinflammatory salicylates
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