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Russian Chemical Bulletin

, Volume 56, Issue 4, pp 774–780 | Cite as

Phosphorus-containing derivatives of 2,6-di(tert-butyl)phenol: The antioxidant activity and properties of the corresponding phenoxyl radicals

  • V. Yu. Tyurin
  • Yu. A. Gracheva
  • E. R. MilaevaEmail author
  • A. A. Prishchenko
  • M. V. Livantsov
  • O. P. Novikova
  • L. I. Livantsova
  • A. V. Maryashkin
  • M. P. Bubnov
  • K. A. Kozhanov
  • V. K. Cherkasov
Article

Abstract

The properties of phenoxyl radicals generated by the oxidation of mono-, di-, and triphosphorus derivatives of 2,6-di(tert-butyl)-4-methylphenol (ionol) were studied by ESR. These compounds exist as conformers that are interconvertible with a temperature-dependent rate. Numerical processing of the ESR spectra gave the thermodynamic and activation parameters that characterize the interconversion of the conformers. The antioxidant activities of the compounds were studied in a model oxidation of oleic acid and with biological objects. These phenols efficiently inhibited radical oxidation reactions.

Key words

2,6-di(tert-butyl)phenols phosphonates antioxidant activity phenoxyl radicals ESR 

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References

  1. 1.
    E. Denisov, Handbook of Antioxidants, CRC Press, Boca Raton, New York, 1995, 543 pp.Google Scholar
  2. 2.
    A. A. Prishchenko, M. V. Livantsov, O. P. Novikova, L. I. Livantsova, D. B. Shpakovskii, and E. R. Milaeva, Zh. Obshch. Khim., 2005, 75, 2058 [Russ. J. Gen. Chem., 2005, 75, 1993 (Engl. Transl.)].Google Scholar
  3. 3.
    A. A. Prishchenko, M. V. Livantsov, O. P. Novikova, L. I. Livantsova, D. B. Shpakovskii, and E. R. Milaeva, Zh. Obshch. Khim., 2006, 76, 868 [Russ. J. Gen. Chem., 2006, 76, 794 (Engl. Transl.)].Google Scholar
  4. 4.
    A. A. Prishchenko, M. V. Livantsov, O. P. Novikova, and L. I. Livantsova, Zh. Obshch. Khim., 2006, 76, 871 [Russ. J. Gen. Chem., 2006, 76, 791 (Engl. Transl.)].Google Scholar
  5. 5.
    V. A. Roginskii, Mol. Biol., 1990, 24, 1582 [Mol. Biol., 1990, 24, 1119 (Engl. Transl.)].Google Scholar
  6. 6.
    Yu. A. Vladimirov and A. I. Archakov, Perekisnoe okislenie lipidov v biologicheskikh membranakh [Peroxide Oxidation of Lipids in Biological Membranes], Nauka, Moscow, 1972, 252 pp. (in Russian).Google Scholar
  7. 7.
    H. Ohkawa, N. Onishi, and K. Yagi, Anal. Biochem., 1979, 95, 351.CrossRefGoogle Scholar
  8. 8.
    A. Rieker and H. Kessler, Tetrahedron, 1968, 24, 513.CrossRefGoogle Scholar
  9. 9.
    A. I. Aleksandrov, N. N. Bubnov, G. G. Lazarev, Ya. S. Lebedev, A. I. Prokof’ev, and M. V. Serdobov, Izv. Akad. Nauk SSSR, Ser. Khim., 1976, 515 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1976, 25 (Engl. Transl.)].Google Scholar
  10. 10.
    H. Heller and H. McConnell, J. Chem. Phys., 1960, 32, 1535.CrossRefGoogle Scholar
  11. 11.
    G. K. Fraenkel, J. Phys. Chem., 1967, 71, 139.CrossRefGoogle Scholar
  12. 12.
    E. N. Frankel, Autooxidation in Food and Biological Systems, Eds M. Simic and M. Karel, Plenum, New York, 1980, 183.Google Scholar
  13. 13.
    V. V. Ershov, G. A. Nikiforov, and A. A. Volod’kin, Prostranstvenno-zatrudnennye fenoly [Sterically Hindered Phenols], Khimiya, Moscow, 1972, 352 pp. (in Russian).Google Scholar

Copyright information

© Springer Science+Business Media, Inc. 2007

Authors and Affiliations

  • V. Yu. Tyurin
    • 1
  • Yu. A. Gracheva
    • 1
  • E. R. Milaeva
    • 1
    Email author
  • A. A. Prishchenko
    • 1
  • M. V. Livantsov
    • 1
  • O. P. Novikova
    • 1
  • L. I. Livantsova
    • 1
  • A. V. Maryashkin
    • 1
  • M. P. Bubnov
    • 2
  • K. A. Kozhanov
    • 2
  • V. K. Cherkasov
    • 2
  1. 1.Department of ChemistryM. V. Lomonosov Moscow State UniversityMoscowRussian Federation
  2. 2.G. A. Razuvaev Institute of Organometallic ChemistryRussian Academy of SciencesNizhny NovgorodRussian Federation

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