Photo- and thermal-oxidation studies on methyl and phenyl linoleate: Anti-oxidant behaviour and rates of reaction

Chemistry and Physics of Lipids

Volumn 107, Issue 1, 2000, Pages 107-120

  Chacón, Jorge N ^a   Gaggini, Paul ^a   Sinclair, Roy S ^a   Smith, Frank J ^a  

^a UNIVERSITY OF THE WEST OF SCOTLAND   (United Kingdom)

Author keywords

Anti oxidants; Free radical; High performance liquid chromatography; Linoleate esters; Photo oxidation; Singlet oxygen; Thermal oxidation

Indexed keywords

ANTIOXIDANT; LINOLEIC ACID; POLYUNSATURATED FATTY ACID;

ARTICLE; AUTOOXIDATION; COMPETITIVE INHIBITION; COMPLEX FORMATION; DRUG DETERMINATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; LIPID PEROXIDATION; PRIORITY JOURNAL; REACTION ANALYSIS; THERMAL ANALYSIS;

ANTIOXIDANTS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; KINETICS; LINOLEIC ACIDS; OXIDATION-REDUCTION; OXYGEN; PHOTOCHEMISTRY; SINGLET OXYGEN; SOLVENTS; SPECTROPHOTOMETRY, ULTRAVIOLET;

EID: 0034284056     PISSN: 00093084     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0009-3084(00)00157-2     Document Type: Article

References (24)

1. Adachi S., Ishiguro T., Matsuno R. Autoxidation kinetics for fatty acids and their esters. J. Am. Oil Chem. Soc. 72:1995;547-551.
2. Banni S., Contini M.S., Angioni E., Deiana M., Dessi M.A., Delis M.P., Carta G., Corongiu F. A novel approach to study linoleic acid autoxidation: importance of simultaneous detection of the substrate and its derivative oxidation products. Free Radic. Res. 25:1996;43-53.
3. Bryans, D., 1991. Dye-sensitised photo-oxidation reactions in model membranes. Ph.D. thesis, Paisley College of Technology, CNAA.
4. Chacón, J.N., 1986. Dye photosensitised oxidation of oleic and linoleic esters. Ph.D. thesis, Paisley College of Technology, CNAA.
5. Chacón J.N., Jamieson G.R., Sinclair R.S. Dye sensitised photo-oxidation of the methyl and phenyl esters of oleic and linoleic acids. Chem. Phys. Lipids. 43:1987;81-89.
6. Chacón J.N., McLearie J., Sinclair R.S. Singlet oxygen yields and radical contributions in the dye sensitised photo-oxidation in methanol of esters of polyunsaturated fatty acids (oleic, linoleic, linolenic and arachadonic). Photochem. Photobiol. 47:1988;647-656.
7. Evans C., Scaiano J.C., Ingold K.U. Absolute kinetics of hydrogen abstraction from α-tocopherol by several reactive species including an alkyl radical. J. Am. Chem. Soc. 114:1992;4589-4593.
8. Frankel E.N. Chemistry of free radical and singlet oxidation of lipids. Prog. Lipid Res. 23:1985;197-221.
9. Girotti A.W. Lipid peroxidation in photodynamic systems. Vigo-Pelfrey C. Membrane Lipid Oxidation. 1:1990;203-218 CRC Press, Boca Raton, FL.
10. Gunstone F.D. Reactions of oxygen and unsaturated fatty acids. J. Am. Oil Chem. Soc. 61:1984;441-447.
11. Hicks M., Gebicki J. A spectrophotometric method for the determination of lipid hydroperoxides. Anal. Biochem. 99:1979;249-253.
12. Hopia A., Huang S.-W., Frankel E.N. Effect of a α-tocopherol and trolox on the decomposition of methyl linoleate hydroperoxides. Lipids. 31:1996;357-365.
13. Iliou J.P., Jourd'heuil D., Robin F., Serkiz B., Guivarc'h P., Volland J.-P., Vilaine J.-P. Kinetics of photoperoxidation of arachidonic acid; molecular mechanisms and effects of antioxidants. Lipids. 27:1992;959-967.
14. McLearie J., Sinclair R.S., Chacón J.N., Smith F.J. Synthesis and characterisation of the photosensitised oxidation reaction products of phenyl esters of linolenic and arachidonic acids. Chem. Phys. Lipids. 62:1992;165-176.
15. McMoneagle, A., 1999. Antioxidant behaviour in photo-oxidation studies of model lipid systems. Ph.D. thesis, University of Paisley.
16. Mukai K., Sawada K., Kohno Y., Terao J.Y. Kinetic study of the prooxidant effect of tocopherol. Hydrogen abstraction from lipid hydroperoxides by tocopheroxyls in solution. Lipids. 28:1993;747-752.
17. Porter N.A., Mills K.A., Carter R.A. A mechanistic study of autoxidation: competing peroxyl H-atom abstraction and re-arrangement. J. Am. Chem. Soc. 116:1994;6690-6696.
18. Pospišil J. Chemical and photochemical behaviour of phenolic antioxidants in polymer stabilisation - a state of the art report, part I. Pol. Deg. Stab. 40:1993;217-232.
19. Rekdal K., Melø T.B. UV-initiated autooxidation of methyl linoleate in micelles - studied by optical absorption. Chem. Phys. Lipids. 75:1995;127-136.
20. Sinclair, R.S., McLearie, J., Chacón, J.N., 1988. The photophysics and photochemistry of some dye sensitisers. In: Moreno, G., Pottier, R.H., Truscott, T.G. (Eds.), Photosensitisation: Molecular, Cellular and Medical Aspects. NATO ASI Series H15, pp. 53-62.
21. Tanielian C., Mechin R. Reaction and quenching of singlet molecular oxygen with esters of polyunsaturated fatty acids. Photochem. Photobiol. 59:1994;263-268.
22. Yamamura T., Ishida T., Tatara H., Nishiyama T. Chain breaking fused heterocyclic antioxidants: antioxidant activities of 9-H-xanthene-2,7-diols and α-tocopherol upon liposomal membranes. J. Am. Oil Chem. Soc. 74:1997;739-744.
23. Yamauchi R., Miyake N., Kato K., Ueno Y. Reaction of α-tocopherol with alkyl and alkylperoxyl radicals of methyl linoleate. Lipids. 28:1993;201-206.
24. Yasaei P.M., Yang G.C., Warner C.R., Daniels D.H., Ku Y. Singlet oxygen oxidation of lipids resulting from photochemical sensitisers in the presence of antioxidants. J. Am. Oil Chem. Soc. 73:1996;1177-1181.