Reaction of α-tocopherol in heated bulk phase in the presence of methyl linoleate (13S)-hydroperoxide or methyl linoleate

Lipids

Volumn 33, Issue 1, 1998, Pages 77-85

  Yamauchi, Ryo ^a   Goto, Kumiko ^a   Kato, Koji ^a  

^a GIFU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

12,13 EPOXY 9 (ALPHA TOCOPHEROXY) 10 OCTADECENOIC ACID METHYL ESTER; 13 HYDROPEROXY 9,11 OCTADECADIENOIC ACID METHYL ESTER; 13 OXO 9,11 OCTADECADIENOIC ACID METHYL ESTER; 9 (ALPHA TOCOPHEROXY) 10,12 OCTADECADIENOIC ACID METHYL ESTER; ALPHA TOCOPHEROL; UNCLASSIFIED DRUG;

ARTICLE; BIOACCUMULATION; DECOMPOSITION; LIPID COMPOSITION; OXIDATION; REACTION ANALYSIS; STEREOISOMERISM;

EID: 0031910317     PISSN: 00244201     EISSN: None     Source Type: Journal    
DOI: 10.1007/s11745-998-0182-1     Document Type: Article

References (30)

1. Gardner, H.W. (1987) Reactions of Hydroperoxides - Products of High Molecular Weight, in Autoxidation of Unsaturated Lipids, (Chan, H.W.-S., ed.) pp. 51-93, Academic Press, London.
2. Frankel, E.N., and Gardner, H.W. (1989) Effect of α-Tocopherol on the Volatile Thermal Decomposition Products of Methyl Linoleate Hydroperoxides, Lipids 24, 603-608.
3. Hopia, A., Huang, S.-W., and Frankel, E.N. (1996) Effect of α-Tocopherol and Trolox on the Decomposition of Methyl Linoleate Hydroperoxides, Lipids 31, 357-365.
4. Burton, G.W., and Ingold, K.U. (1981) Autoxidation of Biological Molecules. 1. The Antioxidant Activity of Vitamin E and Related Chain-Breaking Antioxidants in vitro, J. Am. Chem. Soc. 103, 6472-6477.
5. Niki, E., Saito, T., Kawakami, A., and Kamiya, Y. (1984) Inhibition of Oxidation of Methyl Linoleate in Solution by Vitamin E and Vitamin C, J. Biol. Chem. 259, 4177-4182.
6. Winterle, J., Dulin, D., and Mill, T. (1984) Products and Stoichiometry of α-Tocopherol with Alkylperoxyl Radicals, J. Org. Chem. 49, 491-495.
7. Matsuo, M., Matsumoto, S., Iitaka, Y., and Niki, E. (1989) Radical-Scavenging Reactions of Vitamin Hand Its Model Compound, 2,2,5,7,8-Pentamethylchroman-6-ol, in a tert-Butylperoxyl Radical-Generating System, J. Am. Chem. Soc. 111, 7179-7185.
8. Yamauchi, R., Matsui, T., Satake, Y., Kato, K., and Ueno, Y. (1989) Reaction Products of α-Tocopherol with a Free Radical Initiator, 2,2′-Azobis(2,4-dimethylvaleronitrile), Lipids 24, 204-209.
9. Yamauchi, R., Matsui, T., Kato, K., and Ueno, Y. (1990) Reaction Products of α-Tocopherol with Methyl Linoleate-Peroxyl Radicals, Lipids 25, 152-158.
10. Liebler, D.C., Baker, P.F., and Kaysen, K.L. (1990) Oxidation of Vitamin E: Evidence for Competing Autoxidation and Peroxyl Radical Trapping Reactions of the Tocopheroxyl Radical, J. Am. Chem. Soc. 112, 6995-7000.
11. Urano, S., and Matsuo, M. (1976) A Radical Scavenging Reaction of α-Tocopherol with Methyl Radical, Lipids 11, 380-383.
12. Urano, S., Yamanoi, S., Hattori, Y., and Matsuo, M. (1977) Radical Scavenging Reactions of α-Tocopherol II. The Reaction with Some Alkyl Radicals, Lipids 12, 105-108.
13. Yamauchi, R., Miyake, N., Kato, K., and Ueno, Y. (1993) Reaction of α-Tocopherol with Alkyl and Alkylperoxyl Radicals of Methyl Linoleate, Lipids 28, 201-206.
14. Gardner, H.W., Eskins, K., Grams, G.W., and Inglett, G.E. (1972) Radical Addition of Linoleic Hydroperoxides to α-Tocopherol or the Analogous Hydroxychroman, Lipids 7, 324-334.
15. Kaneko, T., and Matsuo, M. (1985) The Radical-Scavenging Reactions of a Vitamin E Model Compound, 2,2,5,7,8-Pentamethylchroman-6-ol, with Radicals from the Fe(II)-Induced Decomposition of a Linoleic Acid Hydroperoxide, (9Z,11E)-13-Hydroperoxy-9,11-octadecadienoic Acid, Chem. Pharm. Bull. 33, 1899-1905.
16. Yamauchi, R., Yamamoto, N., and Kato, K. (1995) Iron-Catalyzed Reaction Products of α-Tocopherol with Methyl 13(S)-Hydroperoxy-9(Z), 11(E)-octadecadienoate, Lipids 30, 395-404.
17. Yamauchi, R., Kato, K., and Ueno, Y. (1988) Formation of Trimers of α-Tocopherol and Its Model Compound, 2,2,5,7,8-Pentamethylchroman-6-ol in Autoxidizing Methyl Linoleate, Lipids 23, 779-783.
18. Yamauchi, R., Kato, K., and Ueno, Y. (1995) Free-Radical Scavenging Reactions of α-Tocopherol During the Autoxidation of Methyl Linoleate in Bulk Phase, J. Agric. Food Chem. 45, 1455-1461.
19. Nelan, D.R., and Robeson, C.D. (1962) The Oxidation Products from α-Tocopherol and Potassium Ferricyanide and Its Reaction with Ascorbic and Hydrochloric Acids, J. Am. Chem. Soc. 84, 2963-2965.
20. Gardner, H.W. (1975) Isolation of a Pure Isomer of Linoleic Acid Hydroperoxide, Lipids 10, 248-252.
21. Chan, H.W.-S., and Levett, G. (1977) Autoxidation of Methyl Linoleate. Separation and Analysis of Isomeric Mixtures of Methyl Linoleate Hydroperoxides and Methyl Hydroxylinoleates, Lipids 12, 99-104.
22. Gardner, H.W., Kleiman, R., and Weisleder, D. (1974) Homolytic Decomposition of Linoleic Acid Hydroperoxide: Identification of Fatty Acid Products, Lipids 9, 696-706.
23. Hamberg, M. (1975) Decomposition of Unsaturated Fatty Acid Hydroperoxides by Hemoglobin: Structures of Major Products of 13L-Hydroperoxy-9,11-octadecadienoic Acid, Lipids 10, 87-92.
24. Frankel, E.N., Evans, C.D., and Cowan, J.C. (1960) Thermal Dimerization of Fatty Ester Hydroperoxides, J. Am. Oil Chem. Soc. 57, 418-424.
25. Whitlock, C.B., and Nawar, W.W. (1976) Thermal Oxidation of Mono-Unsaturated Short Chain Fatty Acids: Ethyl 3-Hexenoate, J. Am. Oil Chem. Soc. 53, 586-591.
26. Paulose, M.M., and Chang, S.S. (1978) Chemical Reactions Involved in the Deep-Fat Frying of Foods: VIII. Characterization of Nonvolatile Decomposition Products of Triolein, J. Am. Oil Chem. Soc. 55, 375-380.
27. Chan, H.W.-S. (1987) The Mechanism of Autoxidation, in Autoxidation of Unsaturated Lipids (Chan, H.W.-S., ed.) pp. 1-16, Academic Press, London.
28. Frankel, E.N. (1980) Lipid Oxidation, Prog. Lipid Res. 19, 1-22.
29. Porter, N.A., and Wujek, D.G. (1984) Autoxidation of Polyunsaturated Fatty Acids, an Expanded Mechanistic Study, J. Am. Chem. Soc. 106, 2626-2629.
30. Chan, H.W.-S., Levett, G., and Matthew, J.A. (1978) Thermal Isomerization of Methyl Linoleate Hydroperoxides. Evidence of Molecular Oxygen as a Leaving Group in a Radical Rearrangement, J. Chem. Soc., Chem. Commun., 756-757.