Effect of polar solvents on β-carotene radical precursor

Abstract

β-Carotene forms radicals in chloroform upon photo-excitation (i) in the femtosecond time-scale by direct electron ejection into chloroform and (ii) in the microsecond time-scale by secondary reactions with chloroform radicals formed in the faster reactions. The precursor for β-carotene radical cation decays in a second-order reaction in the mixed solvents, with a rate decreasing for increasing dielectric constant of cosolvent (acetic acid < ethanol < acetonitrile∼methanol). The precursor is assigned as an ion pair from which the β-carotene radical cation is formed in neat chloroform, but in more polar solvents it reacts at least partly through disproportionation in a bimolecular reaction promoted by the presence of ions. The stabilization of the radical precursor by increased solvent polarity, allowing for deactivation of the precursor by an alternative reaction channel, is discussed in relation to the balance of pro- and antioxidative properties of β-carotene at lipid/water interfaces.

• β-Carotene
• radical
• solvent effect
• antioxidant

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Erratum