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Issue 2, 2014
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Efficient scavenging of β-carotene radical cations by antiinflammatory salicylates

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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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Article information


Submitted
23 Oct 2013
Accepted
25 Nov 2013
First published
12 Dec 2013

Food Funct., 2014,5, 291-294
Article type
Paper

Efficient scavenging of β-carotene radical cations by antiinflammatory salicylates

H. Cheng, R. Liang, R. Han, J. Zhang and L. H. Skibsted, Food Funct., 2014, 5, 291
DOI: 10.1039/C3FO60519A

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