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Hydroxyanthraquinones Carminic Acid and Chrysazin Anodic Oxidation
Authors:Eric de Souza Gil  Severino Carlos B de Oliveira  Ana Maria de Oliveira‐Brett
Institution:1. Departamento de Química, Faculdade de Ciências e Tecnologia, Universidade de Coimbra, 3004‐535 Coimbra, Portugal;2. Faculdade de Farmácia, Universidade Federal de Goiás, Setor Universitário, 74605‐220, Goiania, Goiás, Brasil
Abstract:The anodic oxidation of the hydroxyanthraquinones carminic acid (CA) and chrysazin (CR) was investigated. The oxidation of CA proceeds in a pH‐dependent cascade mechanism, concerning the hydroquinone, the catechol and the 3‐OH groups in the anthraquinone moiety. The oxidation of the hydroquinone following the catechol electron‐donating groups occurs first at low positive potentials, the 3‐OH group is oxidized irreversibly at a higher potential. The oxidation of CR is pH‐dependent and occurs in successive steps. Oxidation of the hydroquinone tautomer in the CR‐ring occurs first, and the symmetrical 1‐OH and 8‐OH groups are irreversibly oxidized at the same higher potential.
Keywords:Hydroxyanthraquinones  Carminic acid  Chrysazin  Oxidation mechanism  Tautomerism
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