Efficient scavenging of β-carotene radical cations by antiinflammatory salicylates

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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 k = 3.2 × 10 L mol s in 9:1 v/v chloroform-methanol at 23 °C, less efficiently by the anion of salicylic acid with 2.2 × 10 L mol s, 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.
Original languageEnglish
JournalFood & Function
Volume5
Issue number2
Pages (from-to)291-294
Number of pages4
ISSN2042-6496
DOIs
Publication statusPublished - 2014

ID: 101954154