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Synthesis and antioxidant activity of sterically hindered bis-pyrocatechol thioethers

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Abstract

A reaction of 3,5-di-tert-butyl-o-benzoquinone with 1,2- and 1,6-dithiols was used to obtain the corresponding bis-pyrocatechol thioethers; a comparative evaluation of their antioxidant activity was carried out. The synthesized thioethers, 2-(4,6-di-tert-butyl-2,3-dihydroxyphenylsulfanyl)acetic acid, and 3,5-di-tert-butylpyrocatechol were studied in the reaction with diphenylpicrylhydrazyl radical. The influence of these compounds on the autooxidation process of oleic (cis-octadec-9-enoic) acid was studied. The antioxidant activity of bis-pyrocatechol thioethers was manifested in the reaction with diphenylpicrylhydrazyl radical in the process of autooxidation of oleic acid, which was confirmed by the experimental EC50 values, the data on the number of transformed molecules of stable radical (nDPPH), and the relative content of oleic acid hydroperoxides. Bis-pyrocatechol thioethers were found to exhibit the inhibitory activity in the course of oxidation of glutathione induced by 2,2’-azobis(2-amidinopropane) dihydrochloride.

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Authors and Affiliations

  1. Astrakhan State Technical University, 16 ul. Tatishcheva, 414056, Astrakhan, Russian Federation

    I. V. Smolyaninov, O. V. Pitikova, E. S. Rychagova, E. O. Korchagina, S. A. Smolyaninova & N. T. Berberova

  2. Southern Scientific Center, Russian Academy of Sciences, 41 ul. Chekhova, 344006, Rostov on Don, Russian Federation

    I. V. Smolyaninov

  3. G. A. Razuvaev Institute of Organometallic Chemistry, Russian Academy of Sciences, 49 ul. Tropinina, 603950, Nizhny Novgorod, Russian Federation

    A. I. Poddel’sky

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  1. I. V. Smolyaninov
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  2. O. V. Pitikova
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  3. E. S. Rychagova
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  4. E. O. Korchagina
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  5. A. I. Poddel’sky
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  6. S. A. Smolyaninova
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  7. N. T. Berberova
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Correspondence to I. V. Smolyaninov.

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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 12, pp. 2861–2867, December, 2016.

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Smolyaninov, I.V., Pitikova, O.V., Rychagova, E.S. et al. Synthesis and antioxidant activity of sterically hindered bis-pyrocatechol thioethers. Russ Chem Bull 65, 2861–2867 (2016). https://doi.org/10.1007/s11172-016-1669-4

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  • DOI: https://doi.org/10.1007/s11172-016-1669-4

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