Advertisement

Kinetics and Catalysis

, Volume 45, Issue 6, pp 813–820 | Cite as

Correlation between the structure and inhibiting activity of phenosan derivatives

  • N. M. Storozhok
  • M. G. Perevozkina
  • G. A. Nikiforov
  • I. F. Rusina
  • E. B. Burlakov
Peroxides-XI

Abstract

Sterically hindered phenolic antioxidants (AOs) of the IKhFAN family are characterized as inhibitors of initiated oxidation of methyl oleate in homogeneous chlorobenzene solutions and in aqueous emulsions in the presence of dodecyl sulfate. The IKhFANs inhibit oxidation by scavenging peroxo radicals and by decomposing hydroperoxides to yield molecular products. The effect of an IKhFAN is governed by its chemical structure and by oxidation conditions. The IKhFANs slow down methyl oleate oxidation in lipid solution more effectively than comparable concentrations of α-tocopherol, dibunol, phenosan K, or phenosan ester. The most effective is IKhFAN-10, in which the R3 radical is the shortest (CH3). The inhibiting effect of the AOs weakens markedly with increasing chain length of R3. The specific features of the observed oxidation kinetics are explained by the formation of microheterogeneous systems involving AOs. In these systems, the phenolic OH groups are directed to the micelle center and, as a consequence, can hardly react with RO 2 · radicals. In the IKhFAN group in which R3 ranges from C8H17 to C16H33, the induction period grows in proportion to the number of carbon atoms. In an aqueous emulsion, the overall inhibiting effects of structurally different IKhFANs are similar and weaker than effects in homogeneous solution.

Keywords

Hydroperoxide Chlorobenzene Methyl Oleate Oxidation Kinetic Phenolic Antioxidant 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

REFERENCES

  1. 1.
    Molochkina, E.M., Ozerova, I.B., Braginskaya, F.I., Zorina, O.M., and Shishkina, L.N., in Bioantioksidant (Bioantioxidant), 1998, p. 153.Google Scholar
  2. 2.
    Bogatyrenko, T.N., Burlakova, E.B., and Konradov, A.A., in Bioantioksidant (Bioantioxidant), 1998, p. 26.Google Scholar
  3. 3.
    Shlyapintokh, V.Ya, Karpukhin, O.N., Postnikov, L.M. 1972Khemilyuminestsentnye metody issledovaniya medlennykh khimicheskikh protsessovNaukaMoscow138(Chemiluminescence-Based Methods for Studying Slow Chemical Processes)Google Scholar
  4. 4.
    Fendlez, J.H., Fendlez, E.J. 1975Catalysis in Micellar and Macromolecular SystemsAcademicNew York290Google Scholar
  5. 5.
    Dulitskaya, R.F., Fel’dman, R.I. 1978Praktikum po fizicheskoi i kolloidnoi khimiiVysshaya ShkolaMoscow296(Practical Course of Physical and Colloid Chemistry)Google Scholar
  6. 6.
    Nikiforov, G.A., Belostotskaya, I.S., Vol’eva, V.B., Komissarova, N.L., and Gorbunov, D.V., in Nauchnyi vestnik Tyumenskoi meditsinskoi akademii: Bioantioksidanty (Scientific Bulletin of the Tyumen Academy of Medicine: Bioantioxidants), 2003, p. 50.Google Scholar
  7. 7.
    Roginskii, V.A. 1988Fenol’nye antioksidanty: Reaktsionnaya sposobnost’ i effektivnost’NaukaMoscow247(Phenolic Antioxidants: Reactivity and Effectiveness)Google Scholar
  8. 8.
    Antonovskii, V.L. 1972Organicheskie perekisnye initsiatoryKhimiyaMoscow445(Organic Peroxide Initiators)Google Scholar
  9. 9.
    Ershov, Yu.A., Popkov, V.A., Berlyand, A.S. 1993Obshchaya khimiya. Biofizicheskaya khimiya. Khimiya biogennykh elementovNaukaMoscow560(General Chemistry. Biophysical Chemistry. Chemistry of Biogenic Elements)Google Scholar

Copyright information

© MAIK “Nauka/Interperiodica” 2004

Authors and Affiliations

  • N. M. Storozhok
    • 1
  • M. G. Perevozkina
    • 1
  • G. A. Nikiforov
    • 2
  • I. F. Rusina
    • 2
  • E. B. Burlakov
    • 2
  1. 1.Tyumen State Medical AcademyTyumenRussia
  2. 2.Emanuel Institute of Biochemical PhysicsRussian Academy of SciencesMoscowRussia

Personalised recommendations