Thermally induced formation of conjugated isomers of linoleic acid

European Journal of Lipid Science and Technology

Volumn 107, Issue 3, 2005, Pages 167-172

  Destaillats, Frédéric ^a,b   Angers, Paul ^a  

^a UNIVERSITÉ LAVAL   (Canada)

^b NESTLÉ RESEARCH CENTER   (Switzerland)

Author keywords

Allylic radical reaction; Conjugated linoleic acid; Sigmatropic reaction; Stability; Thermal degradation; Thermal oxidation

Indexed keywords

HYDROGEN; LINOLEIC ACID; LINOLEIC ACID METHYL ESTER; RADICAL; TERT BUTYL HYDROPEROXIDE; UNCLASSIFIED DRUG;

AIR; ARTICLE; ATMOSPHERE; CONJUGATION; GEOMETRY; HEAT TREATMENT; ISOMER; OXIDATION; OXYGENATION; RADICAL REACTION;

EID: 17144417698     PISSN: 14387697     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejlt.200401088     Document Type: Article

References (14)

1. J. Graille: Réactions chimiques induites par la friture. Oléagineux Corps Gras Lipides. 1998, 5, 36-40.
2. E. N. Frankel: Lipid Oxidation. The Oily Press, Dundee (UK) 1998.
3. J. L. Sébédio, A. Grandgirard, J. Prevost: Linoleic acid isomers in heat treated sunflower oils. J Am Oil Chem Soc. 1988, 65, 362-366.
4. P. Juaneda, O. Cordier, S. Gregoire, J. L. Sebedio: Conjugated linoleic acid (CLA) isomers in heat-treated vegetable oils. Oleagineux Corps Gras Lipides. 2000, 8, 94-97.
5. F. Destaillats, P. Angers: Evidence for a [1,5] sigmatropic rearrangement in conjugated linoleic acids in heated oils. Lipids. 2002, 37, 435-438.
6. W. W. Christie, J. L. Sébédio, P. Juanéda: A practical guide to the analysis of conjugated linoleic acid (CLA). INFORM. 2001, 12, 147-152.
7. 12,14. Eur J Lipid Sci Technol. 2003, 105, 3-8.
8. O. Sjovall, A. Kuksis, H. Kallio: Reversed-phase high performance liquid chromatography separation of tert-butyl hydroperoxide oxidation products of unsaturated triacylglycerols. J Chromatogr A. 2001, 905, 119-132.
9. O. Sjovall, A. Kuksis, L. Marai, J. J. Myher: Elution factors of synthetic oxotriacylglycerols as an aid in identification of peroxidized natural triacylglycerols by reversed-phase high performance liquid chromatography with electrospray mass spectrometry. Lipids. 1997, 32, 1211-1218.
10. S. Bergstrom: Autoxidation of linoleic acid. Nature. 1945, 156, 717-718.
11. F. D. Gunstone, T. P. Hilditch: The union of gaseous oxygen with methyl oleate, linoleate, and linolenate. J Chem Soc. 1945, 105, 836-841.
12. N. A. Porter, S. E. Caldwell, K. A. Mills: Mechanisms of free radical oxidation of unsaturated lipids. Lipids. 1995, 30, 277-290.
13. A. R. Brash: Autoxidation of methyl linoleate: identification of the bis-allylic 11-hydroperoxide. Lipids, 2000, 35, 947-952.
14. C. W. Spangler: Thermal [1,j] sigmatropic rearrangements. Chemical Reviews. 1976, 76, 187-217.