Anodic oxidation of 3,4-dihydroxyphenylacetic acid on carbon electrodes in acetic acid solutions. 2010

Slawomir Michalkiewicz, and Agata Skorupa
Institute of Chemistry, Jan Kochanowski University of Humanities and Sciences, Swietokrzyska Street 15G, Kielce, Poland. smich@ujk.kielce.pl

The electrochemical oxidation of 3,4-dihydroxyphenylacetic acid (DOPAC) on a carbon fiber microelectrode (CF) and a glassy carbon macroelectrode (GC) in glacial acetic acid solutions was investigated using voltammetric techniques. Voltammograms recorded at these electrodes show well-defined single waves or peaks. The proposed mechanism of the anodic oxidation of DOPAC consists of two successive one-electron one-proton steps. The loss of the first electron proceeds irreversibly and determines the overall rate of the electrode process. This stage is accompanied by the generation of an unstable phenoxyl radical in position 4 of the aromatic ring. The second stage of the electrode reaction produces substituted orto-quinone as the final product of the electrode process of DOPAC. DOPAC exhibits more antioxidative power than synthetic BHT and can be useful in food protection against reactive oxygen species. The results presented can help to explain biochemical and antioxidative properties of DOPAC in a living cell and can be useful in determination of this compound in real samples.

UI MeSH Term Description Entries
D008839 Microelectrodes Electrodes with an extremely small tip, used in a voltage clamp or other apparatus to stimulate or record bioelectric potentials of single cells intracellularly or extracellularly. (Dorland, 28th ed) Electrodes, Miniaturized,Electrode, Miniaturized,Microelectrode,Miniaturized Electrode,Miniaturized Electrodes
D010084 Oxidation-Reduction A chemical reaction in which an electron is transferred from one molecule to another. The electron-donating molecule is the reducing agent or reductant; the electron-accepting molecule is the oxidizing agent or oxidant. Reducing and oxidizing agents function as conjugate reductant-oxidant pairs or redox pairs (Lehninger, Principles of Biochemistry, 1982, p471). Redox,Oxidation Reduction
D002244 Carbon A nonmetallic element with atomic symbol C, atomic number 6, and atomic weight [12.0096; 12.0116]. It may occur as several different allotropes including DIAMOND; CHARCOAL; and GRAPHITE; and as SOOT from incompletely burned fuel. Carbon-12,Vitreous Carbon,Carbon 12,Carbon, Vitreous
D004583 Electrons Stable elementary particles having the smallest known negative charge, present in all elements; also called negatrons. Positively charged electrons are called positrons. The numbers, energies and arrangement of electrons around atomic nuclei determine the chemical identities of elements. Beams of electrons are called CATHODE RAYS. Fast Electrons,Negatrons,Positrons,Electron,Electron, Fast,Electrons, Fast,Fast Electron,Negatron,Positron
D012996 Solutions The homogeneous mixtures formed by the mixing of a solid, liquid, or gaseous substance (solute) with a liquid (the solvent), from which the dissolved substances can be recovered by physical processes. (From Grant & Hackh's Chemical Dictionary, 5th ed) Solution
D015102 3,4-Dihydroxyphenylacetic Acid A deaminated metabolite of LEVODOPA. DOPAC,Homoprotocatechuic Acid,3,4-Dihydroxyphenylacetic Acid, Monosodium Salt,3,4 Dihydroxyphenylacetic Acid
D019342 Acetic Acid Product of the oxidation of ethanol and of the destructive distillation of wood. It is used locally, occasionally internally, as a counterirritant and also as a reagent. (Stedman, 26th ed) Glacial Acetic Acid,Vinegar,Acetic Acid Glacial,Acetic Acid, Glacial,Glacial, Acetic Acid

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