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Study of ellagic acid electro-oxidation mechanism

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Abstract

Ellagic acid is a biologically active polyphenol found in numerous fruits and vegetables. However, not many papers dealing with the electrochemical properties and protolytic equilibria of ellagic acid have been published so far. The electro-oxidation mechanism of ellagic acid was studied in methanol aqueous media (1:1, v/v) within the pH range of 1.5–9.0, t = 25 ± 1 °C, using cyclic voltammetry on a glassy carbon electrode, and by semiempirical calculations. Results show that oxidation of ellagic acid is a pH-dependent, two-step quasireversible process. The slope of peak 1 indicates the exchange of the same number of electrons and protons within the whole studied pH range; the slope of peak 2 changes with the increase of pH, and three different regions are visible. As protolytic equilibria studies revealed that ellagic acid acts as a diprotic acid in the studied conditions (acidity constants were potentiometrically determined as pK a1 = 5.42 ± 0.01 and pK a2 = 6.76 ± 0.01), it is obvious that the electro-oxidation occurs at the hydroxyl group subjected to dissociation. The three different regions are therefore recognized as regions with different dominating species: unionized molecule (H4A), monoanion (H3A−), and dianion (H2A2−). UV/Vis spectral changes confirmed the proposed equilibria. Heat of formation and electron densities calculated at semiempirical level were used to propose the hydrogen and electron abstraction sites. According to the obtained results, a new mechanism of ellagic acid electro-oxidation is proposed.

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Acknowledgments

The Ministry of Education and Science of Serbia supports this work (grants 172030 and 172035). The reported computational work makes use of results produced by the High-Performance Computing Infrastructure for South East Europe’s Research Communities (HP-SEE), a project cofunded by the European Commission (under contract number 261499) through the Seventh Framework Programme HP-SEE (http://www.hp-see.eu/).

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Authors and Affiliations

  1. Faculty of Chemistry, University of Belgrade, Studentski Trg 12-16, 11158, Belgrade, Serbia

    Aleksandra Z. Simić, Tatjana Ž. Verbić, Milica N. Sentić, Mirjana P. Vojić & Dragan D. Manojlović

  2. Institute of Chemistry, Technology, and Metallurgy, Njegoševa 12, 11000, Belgrade, Serbia

    Ivan O. Juranić

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  1. Aleksandra Z. Simić
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  2. Tatjana Ž. Verbić
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  3. Milica N. Sentić
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  4. Mirjana P. Vojić
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  5. Ivan O. Juranić
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  6. Dragan D. Manojlović
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Correspondence to Tatjana Ž. Verbić.

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Simić, A.Z., Verbić, T.Ž., Sentić, M.N. et al. Study of ellagic acid electro-oxidation mechanism. Monatsh Chem 144, 121–128 (2013). https://doi.org/10.1007/s00706-012-0856-8

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