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A radical scavenging reaction of α-tocopherol with methyl radical

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Lipids

Abstract

To study a radical scavenging reaction of α-tocopherol, it was reacted with methyl radical in dimethyl sulfoxide. Two main products, a geminal dimethyl cyclohexadienone and methyl ether of α-tocopherol, were obtained and these structures were determined by13C nuclear magnetic resonance spectroscopy. The radical methylation data of α-tocopherol suggested that a delocalized radical species would be an intermediate.

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References

  1. Green, J., in “The Fat-Soluble Vitamins,” Edited by H.F. DeLuca and J.W. Suttie, The University of Wisconsin Press, Madison, WI, 1969, p. 293.

    Google Scholar 

  2. Wasserman, R.H., and A.N. Taylor, Annu. Rev. Biochem. 41:182 (1972).

    Article  Google Scholar 

  3. Tappel, A.L., and J. Green, Ann. N.Y. Acad. Sci. 203:12 and 29 (1972).

    PubMed  CAS  Google Scholar 

  4. McCay, P.B., P.M. Pfeifer, and W.H. Stipe, Ibid. 203:62 (1972).

    PubMed  CAS  Google Scholar 

  5. Goodhue, C.T., and H.A. Risley, Biochemistry 4:857 (1965).

    Google Scholar 

  6. Porter, W.L., L.A. Levasseur, and A.S. Henick, Lipids 6:1 (1971).

    Article  PubMed  Google Scholar 

  7. Gardner, H.W., K. Eskins, G.W. Grams, and G.E. Inglett, Ibid. 7:324 (1972).

    Article  CAS  Google Scholar 

  8. Skinner, W.A., Biochem. Biophys. Res. Commun. 15:469 (1964).

    Article  PubMed  CAS  Google Scholar 

  9. Skinner, W.A., and R.M. Parkhurst, Lipids 6:240 (1971).

    CAS  Google Scholar 

  10. Nilsson, J.L.G., H. Sievertsson, and H. Selander, Acta Chem. Scand. 22:3160 (1968).

    CAS  Google Scholar 

  11. Weisler, L., U.S. Patent 2,464,539 (1949).

  12. Bertilsson, B.M., B. Gustafsson, I. Kühn, and K. Torssell, Acta Chem. Scand. 24:3590 (1970).

    Article  CAS  Google Scholar 

  13. Johnson, L.F., and W.C. Jancowski, “Carbon-13 NMR Spectra,” Wiley-Interscience, New York, NY, 1972, Spectrum No. 496.

    Google Scholar 

  14. Matsuo, M., and S. Urano, Tetrahedron 32:229 (1976).

    Article  CAS  Google Scholar 

  15. Bhacca, N.S., F.W. Wehrli, and N.H. Fischer, J. Org. Chem. 38:3618 (1973).

    CAS  Google Scholar 

  16. Sadler, I.H., J. Chem. Soc. Chem. Commun. 809 (1973).

  17. Boguth, W., and H. Niemann, Biochim. Biophys. Acta 248:121 (1971).

    PubMed  CAS  Google Scholar 

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Authors and Affiliations

  1. Tokyo Metropolitan Institute of Gerontology, 35-2 Sakaecho, Itabashi-ku, 173, Tokyo, Japan

    Shiro Urano & Mitsuyoshi Matsuo

Authors
  1. Shiro Urano
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  2. Mitsuyoshi Matsuo
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TMIG-RI No. 3.

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Urano, S., Matsuo, M. A radical scavenging reaction of α-tocopherol with methyl radical. Lipids 11, 380–383 (1976). https://doi.org/10.1007/BF02532844

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  • DOI: https://doi.org/10.1007/BF02532844

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