Interconversion of α-tocopherol and its oxidation products

作者: W.H. Harrison , J.E. Gander , E.R. Blakley , P.D. Boyer

DOI: 10.1016/0006-3002(56)90105-6

关键词: Medicinal chemistryTocopherolNeutral phCytochrome cElectromotive forceQuinoneAscorbic acidEthanolVitamin EChemistryInorganic chemistry

摘要: Abstract α-Tocopheroxide is not readily reduced polarographically and in mixtures with α-tocopherol does give a stable electromotive potential; thus α-tocopheroxide the electromotively active, bivalent oxidation product detectable polarographically. Various experiments are reported on conversion of to α-tocopherylquinone; under weakly acidic conditions forms α-tocopherylquinone, whereas similar ascorbic acid present formed. The formation common intermediate hemi-ketal structure both reactions considered as likely possibility. No was detected spectrophotometrically during slow α-tocopheryl;quinone near neutral pH. Treatment α-tocopherylquinone absolute ethanol hydrochloric acids converts quinone principally α-tocopherol, or closely resembling by pathway involving α-tocopherylhydroquinone; some preparations considerable amounts products unknown Ascorbate act synergistically prevention acceleration cytochrome c linoleate Neither effective without ascorbate. implications these other findings discussed.

参考文章(22)
P.D. Boyer, M. Rabinovitz, E. Liebe, Chemical structure in relation to vitamin E function. Journal of Biological Chemistry. ,vol. 192, pp. 95- 103 ,(1951) , 10.1016/S0021-9258(18)55911-1
Alice. Issidorides, H.A. Mattill, The biological activity of α-tocopherylhydroquinone in rats. Journal of Biological Chemistry. ,vol. 188, pp. 313- 316 ,(1951) , 10.1016/S0021-9258(18)56172-X
Julia B. Mackenzie, Harris Rosenkrantz, Stanley Ulick, Ade T. Milhorat, THE BIOLOGICAL ACTIVITY OF α-TOCOPHERYLHYDROQUINONE AND α-TOCOPHERYLQUINONE Journal of Biological Chemistry. ,vol. 183, pp. 655- 662 ,(1950) , 10.1016/S0021-9258(19)51192-9
P. Karrer, A. Geiger, Über α‐Tocopherol‐chinon Helvetica Chimica Acta. ,vol. 23, pp. 455- 459 ,(1940) , 10.1002/HLCA.19400230159
P. Karrer, R. Escher, H. Fritzsche, H. Keller, B. H. Ringier, H. Salomon, Konstitution und Bestimmung des α‐Tocopherols und einiger ähnlicher Verbindungen Helvetica Chimica Acta. ,vol. 21, pp. 939- 953 ,(1938) , 10.1002/HLCA.193802101124
A.L. Tappel, W.O. Lundberg, P.D. Boyer, Effect of temperature and antioxidants upon the lipoxidase-catalyzed oxidation of sodium linoleate Archives of Biochemistry and Biophysics. ,vol. 42, pp. 293- 304 ,(1953) , 10.1016/0003-9861(53)90359-2
Lee Irvin Smith, Leo J. Spillane, I. M. Kolthoff, The Chemistry of Vitamin E. XXXV. The Behavior of Tocopherols at the Dropping Mercury Electrode1 Journal of the American Chemical Society. ,vol. 64, pp. 447- 451 ,(1942) , 10.1021/JA01254A058
O. S. Privett, F. W. Quackenbush, The relation of synergist to antioxidant in fats Journal of the American Oil Chemists Society. ,vol. 31, pp. 321- 323 ,(1954) , 10.1007/BF02632160
Alice Issidorides, The Antioxygenic Synergism of Various Acids with α-Tocopherol1 Journal of the American Chemical Society. ,vol. 73, pp. 5146- 5148 ,(1951) , 10.1021/JA01155A039