O comportamento eletroquímico da quercetina em meio hidro-alcoólico foi estudado na faixa de pH 2,2-9,2 aplicando-se as técnicas voltametria cíclica, eletrólise com potencial controlado e espectroscopia UV-Vis. Voltamogramas cíclicos para a quercetina mostraram três picos de oxidação e um pico de redução dependente das condições experimentais. Um processo de oxidação envolvendo dois prótons e dois elétrons no primeiro pico conduziu à formação da orto-quinona correspondente, a qual é uma espécie eletroquimicamente ativa e instável, como evidenciado pela dependência do perfil dos voltamogramas cíclicos com a velocidade de variação de potencial, em concordância com um mecanismo do tipo eletroquímico-químico (EC). Eletrólises com potencial controlado geraram três produtos caracterizados por espectroscopia UV-Vis. Um esquema reacional envolvendo as etapas eletroquímica e química foi proposto para a eletro-oxidação da quercetina em solução hidro-alcoólica, com base em dados obtidos da literatura e em evidências experimentais.The electrochemistry of quercetin hydro-alcoholic solutions of pH 2.2 to 9.2 was studied by cyclic voltammetry, controlled-potential electrolysis and UV-Vis spectroscopy. Cyclic voltammograms for quercetin showed three oxidation peaks and one reduction peak depending on the experimental conditions. The two-electron two-proton oxidation process at the first peak led to the formation of the corresponding ortho-quinone, which is an electrochemically active and unstable species, as evidenced by the dependence of the cyclic voltammogram profile on the applied scan rate, in agreement with the EC mechanism. Controlled-potential electrolysis yielded three products as characterized by UV-Vis spectroscopy. A reaction scheme comprising electrochemical and chemical steps was proposed for the electro-oxidation of the quercetin in hydro-alcoholic solutions on basis of experimental evidences obtained in this work and elsewhere.

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We report the electrochemical oxidation of rutin in acetonitrile-sodium phosphate (4:1 (v/v); pH 2.0) in the presence of p-toluenesulfinic acid. Cyclic voltammetry and controlled potential electrolysis were used to study rutin electro-oxidation and to prepare the sulfone derivatives. Chromatographic methods were employed to separate the products and IR, 1 H NMR, 13 C NMR, MS and microanalysis to their characterization. Data from cyclic voltammetry allow the identification of three rutin oxidation processes in the presence of p-toluenesulfinic acid (E p I = 0.56 V, E p II = 0.81 V and E p III = 1.32 V). Only the electrode process around peak I was exhaustively studied. The first oxidation step leads to the formation of the corresponding o-quinone, which participates in a Michael addition reaction with the p-toluenesulfinic acid, forming the 6¢(4-methylphenylsulfonyl)rutin and 6¢(4-methylphenylsulfonyl)quercetin as majority products.