Formation of modified fatty acids and oxyphytosterols during refining of low erucic acid rapeseed oil

Journal of Agricultural and Food Chemistry

Volumn 51, Issue 15, 2003, Pages 4284-4290

  Lambelet, Pierre ^a   Grandgirard, André ^b   Gregoire, Stéphane ^b   Juaneda, Pierre ^b   Sebedio, Jean Louis ^b   Bertoli, Constantin ^a  

^a NESTLÉ RESEARCH CENTER   (Switzerland)

^b CEMAGREF   (France)

Author keywords

Canola oil; Cyclic fatty acid monomers; Deodorization; Oxyphytosterols; Refining; Trans fatty acids

Indexed keywords

6BETA HYDROXYBRASSICASTANOL; 6BETA HYDROXYCAMPESTANOL; 6BETA HYDROXYSITOSTANOL; BRASSICASTEROL OXIDE; ERUCIC ACID; FATTY ACID; LINOLENIC ACID; MONOMER; OXYPHYTOSTEROL; PEROXIDE; PHYTOSTEROL; RAPESEED OIL; TOCOPHEROL; UNCLASSIFIED DRUG;

ARTICLE; BLEACHING; CHEMICAL COMPOSITION; DEODORIZATION; FOOD INDUSTRY; MASS SPECTROMETRY; TEMPERATURE; TIME;

BRASSICA NAPUS VAR. NAPUS; SINAPIS ARVENSIS;

EID: 0038492866     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf030091u     Document Type: Article

References (32)

1. Bockisch, M. Fats and Oils Handbook; AOCS Press: Champaign, IL, 1998; Chapter 7.
2. Bertoli, C.; Delvecchio, A.; Durand, P.; Gumy, D.; Bellini, A.; Stancanelli, M. Formation of trans fatty acids during deodorization of low erucic acid rapeseed oil. Proceedings of the World Conference on Oilseed and Edible Oil Processing; Koseoglu, S. S., Rhee, K. C., Wilson, R. F., Eds.; AOCS Press: Champaign IL, 1998; Vol. 2, pp 67-71.
3. Hénon, G.; Kemény, Z.; Recseg, K.; Zwobada, F.; Kovari, K. Deodorization of vegetable oils. Part 1: Modelling the geometrical isomerization of polyunsaturated fatty acids, J. Am. Oil Chem. Soc. 1999, 76, 73-81.
4. Pelura, T. J. The effect of deodorization time and temperature on the chemical, physical and sensory characteristics of menhaden oil. Diss. Abstr. Int. B 1988, 49, 2012.
5. De Greyt, W. F.; Kellens, M. J.; Huyghebaert, A. Effect of physical refining on selected minor components in vegetable oils. Fett/Lipid 1999, 101, 428-432.
6. Ferrari, R. A.; Schulte, E.; Esteves, W.; Brühl, L.; Mukherjee, K. D. Minor constituents of vegetable oils during industrial processing. J. Am. Oil Chem. Soc. 1996, 73, 587-592.
7. Hénon, G.; Vigneron, P. Y.; Stoclin, B.; Caigniez, J. Rapeseed oil deodorization study using the reponse surface methodology. Eur. J. Lipid Sci. Technol. 2001, 103, 467-477.
8. De Greyt, W. F.; Kellens, M. J.; Huyghebaert, A. D. Polymeric and oxidized triglyceride content of crude and refined vegetable oils - an overview. Fett/Lipid 1997, 99, 287-290.
9. Kemény, Z.; Recseg, K.; Hénon, G.; Kovari, K.; Zwobada, F. Deodorization of vegetable oils: prediction of trans polyunsaturated fatty acid content. J. Am. Oil Chem. Soc. 2001, 78, 973-979.
10. Wolff, R. L. Analysis of α-linolenic acid geometrical isomers in deodorized oils by capillary gas-liquid chromatography on cyanoalkyl polysiloxane stationary phases: A note of caution. J. Am. Oil Chem. Soc. 1994, 71, 907-909.
11. Wolff, R. L. Ubiquité et caractéristiques des isomères trans de l'acide linolénique: une revue. Ol. Corps Gras Lipides 1995, 2, 391-400.
12. Chardigny, J. M.; Wolff, R. L.; Mager, E.; Sébédio, J. L.; Martine, L.; Juanéda, P. Trans mono- and polyunsaturated fatty acids in human milk. Eur. J. Clin. Nutr. 1995, 49, 523-531.
13. Sébédio, J. L.; Prévost, J.; Ribot, E.; Grandgirard, A. Utilization of high performance liquid chromatography as an enrichment step for determination of cyclic fatty acid monomers in heated fats and biological samples. J. Chromatogr. A 1994, 659, 101-109.
14. Lai, S. M.; Gray, J. I.; Zabik, M. E. Evaluation of solid-phase extraction and gas chromatography for determination of cholesterol oxidation products in spray-dried whole egg. J. Agric. Food Chem. 1995, 43, 1122-1126.
15. Aringer, L.; Nordström, L. Chromatographic properties and mass spectrometric fragmentation of dioxygenated C27-, C28-, C29-steroids. Biomed. Mass Spectrom. 1981, 8, 183-203.
16. Dumazer, M.; Farines, M.; Soulier, J. Identification de stérols par spectrométrie de masse. Rev. Fr. Corps Gras 1986, 33, 151-156.
17. Nourooz-Zadeh, J.; Appelqvist, L. A. Isolation and quantitative determination of sterol oxides in plant-based foods: soybean oil and wheat flour. J. Am. Oil Chem. Soc. 1992, 69, 288-293.
18. Dutta, P. C.; Przybylski, R.; Appelqvist, L. A.; Eskin, N. A. M. Formation and analysis of oxidized sterols in frying fat. In Deep Frying. Chemistry, Nutrition and Practical Applications; Perkins, E. G., Erickson, M. D., Eds.; AOCS Press: Champaign IL, 1996; pp 112-150.
19. Dutta, P. C. Studies on phytosterol oxides. 2) Content in some vegetable oils and in French fries prepared in these oils. J. Am. Oil Chem. Soc. 1997, 74, 659-666.
20. Przylbylski, R.; Zambiazi, R.; Li, W. Kinetics of sterol changes during storage and frying of canola oils. Proceedings of the 10th International Rapeseed Congress, Canberra, Australia; The Regional Institute Ltd.: Gosford, NSW, Australia, 1999.
21. Martin, J. C.; Nour, M.; Lavillonnière, F.; Sébédio, J. L. Effect of fatty acid positional distribution and triacylglycerol composition on lipid by-products formation during heat treatment: II trans isomers. J. Am. Oil Chem. Soc. 1998, 75, 1073-1078.
22. Sébédio, J. L.; Grandgirard, A. Cyclic fatty acid: natural sources, formation during heat treatment, synthesis and biological properties. Prog. Lipid Res. 1989, 28, 303-336.
23. Sébédio, J. L.; Catte, M.; Boudier, M. A.; Prévost, J.; Grandgirard, A. Formation of fatty acid geometrical isomers and cyclic fatty acid monomers during the finish frying of frozen prefried potatoes. Food Res. Int. 1996, 29, 109-116.
24. Dobson, G.; Christie, W. W.; Brechany, E. Y.; Sébédio, J. L.; Le Quere, J. L. Silver ion chromatography and gas chromatography-mass spectrometry in the structural analysis of cyclic dienoic acids formed in frying oils. Chem. Phys. Lipids 1995, 75, 171-182.
25. Sébédio, J. L.; Chardigny, J. M. In Frying Oils. Chemistry, Nutrition, and Practical Applications; Perkins, E. G., Erickson, M. D., Eds.; AOCS: Champaign, IL, 1996; pp 183-209.
26. Acar, N.; Chardigny, J. M.; Bonhomme, B.; Almanza, S.; Doly, M.; Sébédio, J. L. Long-term intake of trans (n-3) polyunsaturated fatty acids reduces the b-wave amplitude of electroretinogram in rat. J. Nutr. 2002, 132, 3151-3154.
27. Martin, J. C.; Joffre, F.; Siess, M. H.; Vernevaut, M. F.; Collenot, P.; Genty, M.; Sébédio, J. L. Cyclic fatty acid monomers from heated oil modify the activities of lipid synthesizing and oxidizing enzymes in rat liver. J. Nutr. 2000, 130, 1524-1530.
28. Balchen, S.; Adler-Nissen, J. Deodorization principles. Int. News Fats, Oils Relat. Mater. 1999, 10, 245-254, 262.
29. Romero, A.; Cuesta, C.; Sánchez-Muniz, F. J. Cyclic fatty acids monomers and thermoxidative alteration compounds formed during frying of frozen foods in extra virgin olive oil. J. Am. Oil Chem. Soc. 2000, 77, 1169-1175.
30. Grandgirard, A.; Julliard, F. Etude critique des méthodes de dosage des monomères cycliques dans les huiles chauffées. Rev. Fr. Corps Gras 1983, 30, 123-128.
31. Sébédio, J. L.; de Rasilly, A. Analysis of cyclic fatty acids in fish oil concentrates. Proceeding of the 17th Nordic Lipid Symposium, Imatra, Finland, June 1993; Lipid Forum: Bergen, Norway, 1993; pp 212-216.
32. Frankel, E. N.; Smith, L. M.; Hamblin, C. L.; Creveling, R. K.; Clifford, A. J. Occurrence of cyclic fatty acid monomers in frying oils used for fast foods. J. Am. Oil Chem. Soc. 1984, 61, 87-90.