Electro-oxidation of rutin in the presence of p-toluenesulfinic acid

Abstract

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.

Application of a Cu–chitosan/multiwalled carbon nanotube film-modified electrode for the sensitive determination of rutin

“…The latter species is rapidly dehydrated to yield the final product of 3',4'-diquinone. These results confirm the suggested mechanism for the redox reactions of rutin that have been reported in pervious works [17,[40][41][42]. …”

“…A mechanism for the electrochemical oxidation of rutin has been suggested by several researchers [17,[40][41][42]. According to these reports, the oxidation of rutin occurs at the catechol moiety and results in the formation of the corresponding o-quinone (Scheme 2).…”

Electrochemical Sensor for Determination of Various Phenolic Compounds in Wine Samples Using Fe3O4 Nanoparticles Modified Carbon Paste Electrode

“…The results suggest that the nanoparticles’ presence can facilitate electron transfer between the electrode surface and the redox solution, thereby increasing electro-conductibility. Hence, Fe 3 O 4 nanoparticle was very efficient for developing an electrochemical sensor for the analysis of phenolic compounds [ 23 , 42 , 43 ].…”

Morin hydrate as pro-ecological antioxidant and pigment for polyolefin polymers

“…In this paper, we present the use of morin hydrate, one of the most popular flavonoids, as a natural anti-ageing substance for ethylene-octene rubber. Polyolefins [19][20][21][22][23][24][25][26] are widely used for various purposes, so the stabilisation of this type In our studies, we propose the use of natural, pro-ecological substances, such as flavonoids to protect elastomers against ageing. One of these substances, namely morin hydrate, was incorporated into ethylene-octene rubbers (Engage); then the vulcanisates of Engage containing the antioxidant under investigation were subjected to ageing processes.…”