Skip to main content
SpringerLink
Log in

Comparative evaluation of the antioxidant activity of some ortho-substituted mono- and dialkylphenols with the para-positioned hydroxymethyl group

  • Full Articles
  • Published:
Russian Chemical Bulletin Aims and scope

Abstract

The para-hydroxymethyl derivatives of 2,6-di-tert-butylphenol, 2,6-diisobornylphenol, 2-isobornyl-6-tert-butylphenol, 2-isobornyl-6-methylphenol, and 2-isobornylphenol were synthesized. A comparative evaluation of the antioxidant properties of the synthesized compounds was carried out in in vitro models. The activity of derivatives is predetermined by the number and bulkiness of the substituents at the ortho positions relative to the phenolic OH group and is consistent with the relationships previously identified by us for other phenolic antioxidants.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. V. K. Kolvolter, Russ. Chem. Bull., 2010, 59, 37.

    Article  Google Scholar 

  2. E. V. Kuzakov, E. N. Shmidt, Chem. Nat. Compd., 2000, 36, 245.

    Article  CAS  Google Scholar 

  3. O. A. Zalevskaya, Ya. A. Gur’eva, A. V. Kutchin, Russ. Chem. Rev., 2019, 88, 979.

    Article  CAS  Google Scholar 

  4. I. Yu. Chukicheva, E. V. Buravlev, I. V. Fedorova, M. F. Borisenkov, A. V. Kutchin, Russ. Chem. Bull., 2010, 59, 2276.

    Article  CAS  Google Scholar 

  5. E. V. Buravlev, I. Yu. Chukicheva, O. G. Shevchenko, K. Yu. Suponitsky, A. V. Kutchin, Russ. Chem. Bull., 2016, 65, 1232.

    Article  CAS  Google Scholar 

  6. E. V. Buravlev, I. Yu. Chukicheva, O. G. Shevchenko, A. V. Kutchin, Russ. Chem. Bull., 2017, 66, 297.

    Article  CAS  Google Scholar 

  7. E. V. Buravlev, I. V. Fedorova, O. G. Shevchenko, Russ. Chem. Bull., 2019, 68, 985.

    Article  CAS  Google Scholar 

  8. I. Yu. Chukicheva, E. V. Buravlev, I. A. Dvornikova, I. V. Fedorova, G. A. Chernysheva, O. I. Aliev, V. I. Smol’yakova, A. M. Anishchenko, A. V. Sidekhmenova, M. B. Plotnikov, A. V. Kutchin, Russ. Chem. Bull., 2019, 68, 993.

    Article  CAS  Google Scholar 

  9. T. G. Borovskaya, S. I. Kamalova, V. A. Grigor’eva, M. E. Poluektova, A. V. Vychuzhanina, A. V. Kuchin, I. Yu. Chukicheva, E. V. Buravlev, T. I. Fomina, M. B. Plotnikov, V. E. Goldberg, A. M. Dygai, Bull. Exp. Biol. Med., 2019, 167, 606.

    Article  CAS  Google Scholar 

  10. T. G. Borovskaya, S. I. Kamalova, N. A. Krivova, O. B. Zaeva, M. E. Poluektova, A. V. Vychuzhanina, V. A. Grigor’eva, M. B. Plotnikov, V. E. Goldberg, Bull. Exp. Biol. Med., 2018, 166, 7.

    Article  CAS  Google Scholar 

  11. E. V. Buravlev, I. Yu. Chukicheva, I. A. Dvornikova, A. V. Churakov, A. V. Kutchin, Russ. J. Org. Chem., 2012, 48, 938.

    Article  CAS  Google Scholar 

  12. E. V. Buravlev, I. V. Fedorova, O. G. Shevchenko, A. V. Kutchin, Russ. Chem. Bull., 2019, 68, 1558.

    Article  CAS  Google Scholar 

  13. E. V. Buravlev, I. A. Dvornikova, O. G. Schevchenko, A. V. Kutchin, Chem. Biodiversity, 2019, 16, e1900362.

    Article  CAS  Google Scholar 

  14. E. V. Buravlev, O. G. Shevchenko, A. A. Anisimov, K. Yu. Suponitsky, Eur. J. Med. Chem., 2018, 152, 10.

    Article  CAS  Google Scholar 

  15. I. A. Dvornikova, E. V. Buravlev, I. V. Fedorova, O. G. Shevchenko, I. Yu. Chukicheva, A. V. Kutchin, Russ. Chem. Bull., 2019, 68, 1000.

    Article  CAS  Google Scholar 

  16. M. B. Gavazza, A. Catalá, Int. J. Biochem. Cell Biol., 2003, 35, 359.

    Article  CAS  Google Scholar 

  17. M. B. Gavazza, A. Catalá, Prostaglandins, Leukotrienes Essent. Fatty Acids, 2006, 74, 247.

    Article  CAS  Google Scholar 

  18. R. J. Aitken, S. D. Roman, Oxid. Med. Cell. Longevity, 2008, 1, 15.

    Article  Google Scholar 

  19. O. G. Shevchenko, S. N. Plyusnina, I. Yu. Chukicheva, I. V. Fedorova, A. V. Kutchin, Biochem. (Moscow) Suppl. Ser. A, 2013, 7, 302.

    Article  Google Scholar 

  20. I. Yu. Chukicheva, O. V. Sukrusheva, O. A. Shumova, L. I. Mazaletskaya, O. G. Shevchenko, A. V. Kuchin, Russ. J. Gen. Chem., 2016, 86, 2052.

    Article  CAS  Google Scholar 

  21. I. Yu. Chukicheva, I. V. Fedorova, N. A. Nizovtsev, A. A. Koroleva, O. G. Shevchenko, A. V. Kuchin, Chem. Nat. Compd., 2018, 54, 875.

    Article  CAS  Google Scholar 

  22. O. V. Shchukina, I. Yu. Chukicheva, O. G. Shevchenko, T. A. Kolegova, K. Yu. Suponitsky, A. V. Kutchin, Russ. J. Gen. Chem., 2018, 88, 664].

    Article  CAS  Google Scholar 

  23. I. A. Dvornikova, E. V. Buravlev, I. V. Fedorova, O. G. Shevchenko, I. Yu. Chukicheva, A. V. Kuchin, Chem. Nat. Compd., 2019, 55, 658.

    Article  CAS  Google Scholar 

  24. G. M. Coppinger, T. W. Campbell, J. Am. Chem. Soc., 1953, 75, 734.

    Article  CAS  Google Scholar 

  25. E. V. Buravlev, I. Yu. Chukicheva, A. V. Churakov, A. V. Kutchin, Russ. J. Org. Chem., 2012, 48, 64.

    Article  CAS  Google Scholar 

  26. B. R. Davis, D. M. Gash, P. D. Woodgate, S. D. Woodgate, J. Chem. Soc., Perkin Trans. 1, 1982, 1499.

  27. K. Sevgi, B. Tepe, C. Sarikurkcu, Food Chem. Toxicol., 2015, 77, 12.

    Article  CAS  Google Scholar 

  28. K. N. Chandrashekar, Muralidhara, Theriogenology, 2008, 70, 97.

    Article  CAS  Google Scholar 

  29. C. I. Acker, R. Brandao, A. R. Rosario, C. W. Nogueira, Environ. Toxicol. Pharmacol., 2009, 28, 280.

    Article  CAS  Google Scholar 

  30. S. T. Stefanello, A. S. Prestes, T. Ogunmoyole, S. M. Salman, R. S. Schwab, C. R. Brender, L. Dornelles, J. B. T. Rocha, F. A. A. Soares, Toxicol. in Vitro, 2013, 27, 1433.

    Article  CAS  Google Scholar 

  31. R. Chawla, R. Arora, R. Kumar, A. Sharma, J. Prasad, S. Singh, R. Sagar, P. Chaudhary, S. Shukla, G. Kaur, R. K. Sharma, S. C. Puri, K. L. Dhar, G. Handa, V. K. Gupta, G. N. Qazi, Mol. Cell. Biochem., 2005, 273, 193.

    Article  CAS  Google Scholar 

  32. J. S. Kim, Food Nutr. Sci., 2013, 4, 177.

    CAS  Google Scholar 

  33. T. Asakawa, S. Matsushita, Lipids, 1980, 15, 137.

    Article  CAS  Google Scholar 

  34. J. Takebayashi, J. Chen, A. A. Tai, Methods Mol. Biol., 2010, 594, 287.

    Article  CAS  Google Scholar 

  35. J. J. M. Van den Berg, J. A. F. Opden Kamp, B. H. Lubin, B. Roelofsen, F. A. Kuypers, Free Radical Biol. Med., 1992, 12, 487.

    Article  CAS  Google Scholar 

  36. E. Nagababu, J. M. Rifkind, Biochem. Biophys. Res. Commun., 1998, 247, 592.

    Article  CAS  Google Scholar 

  37. E. Nagababu, M. E. Fabry, R. L. Nagel, J. M. Rifkind, Blood Cells Mol. Dis., 2008, 41, 60.

    Article  CAS  Google Scholar 

  38. E. Nagababu, J. G. Mohanty, S. Bhamidipaty, G. R. Ostera, J. M. Rifkind, Life Sci., 2010, 86, 133.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Institute of Chemistry, Komi Science Center, Ural Branch of the Russian Academy of Sciences, 48 ul. Pervomayskaya, 167000, Syktyvkar, Russian Federation

    E. V. Buravlev, I. V. Fedorova & A. V. Kutchin

  2. Institute of Biology, Komi Science Center, Ural Branch of the Russian Academy of Sciences, 28 ul. Kommunisticheskaya, 167982, Syktyvkar, Russian Federation

    O. G. Shevchenko

Authors
  1. E. V. Buravlev
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. I. V. Fedorova
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. O. G. Shevchenko
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. A. V. Kutchin
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to E. V. Buravlev.

Additional information

Dedicated to Academician of the Russian Academy of Sciences A. M. Muzafarov on the occasion of his 70th birthday.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 8, pp. 1573–1578, August, 2020.

This work was financially supported by the Russian Foundation for Basic Research (Project No. 18-03-00950_a) and the Ministry of Science and Higher Education of the Russian Federation (State Assignment No. AAAA-A18-118011120004-5).

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Buravlev, E.V., Fedorova, I.V., Shevchenko, O.G. et al. Comparative evaluation of the antioxidant activity of some ortho-substituted mono- and dialkylphenols with the para-positioned hydroxymethyl group. Russ Chem Bull 69, 1573–1578 (2020). https://doi.org/10.1007/s11172-020-2937-x

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11172-020-2937-x

Key words

Search

Navigation