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Issue 7, 2016
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Chemical quenching of singlet oxygen by betanin

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Betanin is the best known natural dye belonging to the betacyanin family. In this work, efficient singlet oxygen quenching by betanin in deuterated water with the rate constant 1.20 ± 0.15 × 108 M−1 s−1 is reported, deduced from the 1O2 phosphorescence decays measured as a function of betanin concentration. The quenching occurs by a chemical mechanism, as confirmed by the analysis of the transient absorption kinetics at the probe λ ∼ 535 nm, by comparison of the initial triplet signal amplitude of perinaphthenone acting as the 1O2 photosensitizer with the final bleaching signal of betanin. The main betanin oxidation product is 2-decarboxy-2,3-dehydrobetanin, with its formation observed as the transient absorption signal at λ ∼ 445 nm. LC-MS/MS analysis of the photolyzed solutions supports the product identification as 2-decarboxy-2,3-dehydrobetanin, based on the molecular ion [M]+ observed at m/z 505. Isobetanin also undergoes a similar photooxidation reaction.

Graphical abstract: Chemical quenching of singlet oxygen by betanin

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The article was received on 02 Feb 2016, accepted on 23 May 2016 and first published on 24 May 2016

Article type: Paper
DOI: 10.1039/C6PP00037A
Photochem. Photobiol. Sci., 2016,15, 872-878

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    Chemical quenching of singlet oxygen by betanin

    M. Wendel, S. Nizinski, M. Gierszewski, D. Prukala, M. Sikorski, K. Starzak, S. Wybraniec and G. Burdzinski, Photochem. Photobiol. Sci., 2016, 15, 872
    DOI: 10.1039/C6PP00037A

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