Contribution to further understanding of the evolution of sunflower oil submitted to frying temperature in a domestic fryer: Study by1H Nuclear Magnetic Resonance

Journal of Agricultural and Food Chemistry

Volumn 57, Issue 17, 2009, Pages 7790-7799

  Guillén, Maria D ^a   Uriarte, Patricia S ^a  

^a UNIVERSITY OF THE BASQUE COUNTRY UPV EHU   (Spain)

Author keywords

Acyl groups; Aldehydes; 4 hydroxy trans 2 alkenals; Deep fryer; 1h nuclear magnetic resonance (1h nmr); Degradation; Frying temperature; Polar compounds; Rate of formation; Sunflower oll; Viscosity

Indexed keywords

ALDEHYDE; LINOLEIC ACID; SUNFLOWER OIL; TRIACYLGLYCEROL; VEGETABLE OIL;

ARTICLE; CHEMISTRY; HEAT; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OXIDATION REDUCTION REACTION; TIME; VISCOSITY;

ALDEHYDES; HOT TEMPERATURE; LINOLEIC ACID; MAGNETIC RESONANCE SPECTROSCOPY; OXIDATION-REDUCTION; PLANT OILS; TIME FACTORS; TRIGLYCERIDES; VISCOSITY;

HELIANTHUS;

EID: 69949187604     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf900510k     Document Type: Article

References (44)

1. Guilĺn M.D. Cabo N. Usefulness of the frequency data of the Fourier transform infrared spectra to evaluate the degree of oxidation of edible oils Journal of Agricultural and Food Chemistry 1999 47 2 709-719 DOI 10.1021/jf9808123 (1) Guillén, M. D.; Cabo, N. Usefulness of the frequency data of the Fourier transform infrared spectra to evaluate the degree of oxidation of edible oils. J. Agric. Food Chem. 1999, 47, 709-719. (Pubitemid 29185250)
2. Chang, S. S.; Peterson, R. J.; Ho, C. T. Chemical reactions involved in the deep-fat frying of foods. J. Am. Oil Chem. Soc. 1978, 55, 718-727
3. Peled, M.; Gutfinger, T.; Letan, A. Effect of water and BHT on stability of cottonseed oil during frying. J. Sci. Food Agric. 1975, 26, 1655-1666
4. Takeoka, G. R.; Full, G. H.; Dao, L. T. Effect of heating on the characteristics and chemical composition of selected frying oils and fats. J. Agric. Food Chem. 1997, 45, 3244-3249.
5. Waltking, A. E.; Wessels, H. Chromatographic separation of polar and nonpolar components of frying fats. J. Assoc. Off. Anal. Chem. 1981, 64, 1329-1330.
6. Totoki, T.; Hatanaka, H. Assessment of new TLC method for measuring total polar compounds in deteriorated oils. J. Oleo Sci. 2001, 50, 569-573.
7. Stier, R. F. Tests to monitor quality of deep-frying fats and oils. Eur. J. Lipid Sci. Technol. 2004, 106, 766-771.
8. Kaufmann, A.; Ryser, B.; Suter, B. Comparison of different methods to determine polar compounds in frying oils. Eur. Food Res. Technol. 2001, 213, 377-380.
9. Marmesat S. Rodrigues E. Velasco J. Dobarganes C. Quality of used frying fats and oils: Comparison of rapid tests based on chemical and physical oil properties International Journal of Food Science and Technology 2007 42 5 601-608 DOI 10.1111/j.1365-2621.2006.01284.x (9) Marmesat, S.; Rodrigues, E.; Velasco, J; Dobarganes, C. Quality of used frying fats and oils: comparison of rapid tests based on chemical and physical oil properties. Int. J. Food Sci. Technol. 2007, 42, 601608. (Pubitemid 46616320)
10. Choe, E.; Min, D. B. Chemistry of deep-fat frying oils. J. Food Sci. 2007, 72, R77-R86.
11. 1H nuclear magnetic resonance. J. Sci. Food Agric. 2005, 55, 2413-2420.
12. Guillen M.D. Ruiz A. Study by proton nuclear magnetic resonance of the thermal oxidation of oils rich in oleic acyl groups JAOCS, Journal of the American Oil Chemists' Society 2005 82 5 349-355 J11059 (12) Guillén, M. D.; Ruiz, A. Study by proton nuclear magnetic resonance of the thermal oxidation of oils rich in oleic acyl groups. J. Am. Oil Chem. Soc. 2005, 82, 349-355. (Pubitemid 43066417)
13. Guillen M.D. Ruiz A. Monitoring the oxidation of unsaturated oils and formation of oxygenated aldehydes by proton NMR European Journal of Lipid Science and Technology 2005 107 1 36-47 DOI 10.1002/ejlt.200401056 (13) Guillén, M. D.; Ruiz, A. Monitoring the oxidation of unsaturated oils and formation of oxygenated aldehydes by proton NMR. Eur. J. Lipid Sci. Technol. 2005, 107, 36-47. (Pubitemid 40312230)
14. Gullen M.D. Ruiz A. Monitoring of heat-induced degradation of edible oils by proton NMR European Journal of Lipid Science and Technology 2008 110 1 52-60 DOI 10.1002/ejlt.200600299 (14) Guillén, M. D.; Ruiz, A. Monitoring of heat-induced degradation of edible oils by proton NMR. Eur. J. Lipid Sci. Technol. 2008, 110, 5260. (Pubitemid 351184989)
15. 1H NMR) in sunflower oil during the storage. J. Agric. Food Chem. 2007, 55, 10729-10736.
16. Guillen M.D. Ruiz A. Formation of hydroperoxy- and hydroxyalkenals during thermal oxidative degradation of sesame oil monitored by proton NMR European Journal of Lipid Science and Technology 2004 106 10 680-687 DOI 10.1002/ejlt.200401026 (16) Guillén, M. D.; Ruiz, A. Formation of hydroperoxy and hydroxyalkenals during thermal oxidative degradation of sesame oil monitored by proton NMR. Eur. J. Lipid Sci. Technol. 2004, 106, 680-687. (Pubitemid 39530785)
17. Johnson, L. F.; Shoolery, J. N. Determination of unsaturation and average molecular weight of natural fats by nuclear magnetic resonance (NMR). Anal. Chem. 1962, 34, 1136-1139.
18. 13C NMR of virgin olive oil. An overview. Magn. Reson. Chem. 1997, 35, S133-S145.
19. Miyake Y. Yokomizo K. Matsuzaki N. Determination of unsaturated fatty acid composition by high-resolution nuclear magnetic resonance spectroscopy JAOCS, Journal of the American Oil Chemists' Society 1998 75 9 1091-1094 (19) Miyake, Y.; Yokomizo, K.; Matsuzaki, N. Determination of unsaturated fatty acid composition by high-resolution nuclear magnetic resonance spectroscopy. J. Am. Oil Chem. Soc. 1998, 75, 10911094. (Pubitemid 128567003)
20. 1H nuclear magnetic resonance as a fast tool for determining the composition of acyl chains in acylglycerol mixtures European Journal of Lipid Science and Technology 2003 105 9 502-507 DOI 10.1002/ejlt.200300799 (20) Guillén, M. D.; Ruiz, A. 1H nuclear magnetic resonance as a fast tool for determining the composition of acyl chains in acylglycerol mixtures. Eur. J. Lipid Sci. Technol. 2003, 105, 502-507. (Pubitemid 37206153)
21. 1H nuclear magnetic resonance. J. Sci. Food Agric. 2003, 83, 338-346.
22. Kochhar S.P. Gertz C. New theoretical and practical aspects of the frying process European Journal of Lipid Science and Technology 2004 106 11 722-727 DOI 10.1002/ejlt.200400996 (22) Kochhar, S. P.; Gertz, C. New theoretical and practical aspects of the frying process. Eur. J. Lipid Sci. Technol. 2004, 106, 722-727. (Pubitemid 39662716)
23. Guillen M.D. Ruiz A. Rapid simultaneous determination by proton NMR of unsaturation and composition of acyl groups in vegetable oils European Journal of Lipid Science and Technology 2003 105 11 688-696 DOI 10.1002/ejlt.200300866 (23) Guillén, M. D.; Ruiz, A. Rapid simultaneous determination by proton NMR of unsaturation and composition of acyl groups in vegetable oils. Eur. J. Lipid Sci. Technol. 2003, 105, 688-696. (Pubitemid 37533026)
24. Dobarganes, M. C.; Perez-Camino, M. C. Fatty acid composition: a useful tool for the determination of alteration level in heated fats. Rev. Fr. Corps Gras. 1988, 35, 67-70.
25. 1H nuclear magnetic resonance in the study of edible oils and fats. Trends Food Sci. Technol. 2001, 12, 328-338.
26. 1H nuclear magnetic resonance data. Food Chem. 2009, 116, 183-192.
27. Guillén, M. D; Uriarte, P. S. Evidence of the very early formation in sunflower oil under frying conditions of 4-hydroxy-trans-2-nonenal and other toxic aldehydes. 6th Euro Fed Lipid Congress, Athens, Greece, Sept 7-10; Euro Fed Lipid: Frankfurt, Germany, 2008; p 296.
28. Seppanen, C. M.; Csallany, A. S. The effect of intermittent and continuous heating of soybean oil at frying temperature on the formation of 4-hydroxy-2-trans-nonenal and other α,β-unsaturated hydroxyaldehydes. J. Am. Oil Chem. Soc. 2006, 83, 121-127.
29. Takeoka, G. R.; Buttery, R. G.; Perrino, C. T., Jr. Synthesis and occurrence of oxoaldehydes in used frying oils. J. Agric. Food Chem. 1995, 43, 22-26
30. Noordermeer, M. A.; Feussner, I.; Kolbe, A.; Veldink, G. A.; Vliegenthart Oxygenation of (3Z)-alkenals to 4-hydroxy-(2E)alkenals in plant extracts: A nonenzymatic process. Biochem. Biophys. Res. Commun. 2000, 277, 112-116.
31. Lee, S. H.; Elipe, M. V. S.; Arora, J. S.; Blair, I. A. Dioxododecenoic acid: A lipid hydroperoxide-derived bifunctional electrophile responsible for etheno DNA adduct formation. Chem. Res. Toxicol. 2005, 18, 566-578.
32. Schneider C. Tallman K.A. Porter N.A. Brash A.R. Two distinct pathways of formation of 4-hydroxynonenal. Mechanisms of nonenzymatic transformation of the 9- and 13-hydroperoxides of linoleic acid to 4-hydroxyalkenals Journal of Biological Chemistry 2001 276 24 20831-20838 DOI 10.1074/jbc.M101821200 (32) Schneider, C.; Tallman, K. A.; Porter, N. A.; Brash, A. R. Two distinct pathways of formation of 4-hydroxynonenal. Mechanisms of nonenzymatic transformation of the 9- and 13-hydroperoxides of linoleic acid to 4-hydroxyalkenals. J. Biol. Chem. 2001, 276, 20831-20838. (Pubitemid 37413062)
33. Gardner, H. W. 9-hydroxy-traumatin, a new metabolite of the lipoxygenase pathway. Lipids 1998, 33, 745-749.
34. Salomon, R. G. Isolevuglandins, oxidatively truncated phospholipids, and atherosclerosis. Ann. N. Y. Acad. Sci. 2005, 1043, 327-342.
35. Sun, M.; Salomon, R. G. Oxidative fragmentation of hydroxy octadecadienoates generates biologically active γ-hydroxyalkenals. J. Am. Chem. Soc. 2004, 126, 5699-5708.
36. Zhang, W.; Sun, M.; Salomon, R. G. Preparative singlet oxygenation of linoleate provides doubly allylic dihydroperoxides: Putative intermediates in the generation of biologically active aldehydes in vivo. J. Org. Chem. 2006, 71 (15), 5607-5615.
37. Deng Y. Salomon R.G. Total synthesis of oxidized phospholipids. 3. The (11E)-9-hydroxy-13-oxotridec-11-enoate ester of 2-lysophosphatidylcholine Journal of Organic Chemistry 2000 65 20 6660-6665 DOI 10.1021/jo000809u (37) Deng, Y.; Salomon, R. Total synthesis of oxidized phospholipids. 3. The (11E)-9-Hydroxy-13-oxotridec-11-enoate ester of 2-lysophosphatidylcholine. J. Org. Chem. 2000, 65, 6660-6665. (Pubitemid 30751997)
38. Poli G. Schaur R.J. Siems W.G. Leonarduzzi G. 4-Hydroxynonenal: A membrane lipid oxidation product of medicinal interest Medicinal Research Reviews 2008 28 4 569-631 DOI 10.1002/med.20117 (38) Poli, G.; Schaur, R. J; Siems, W. G; Leonarduzzi, G. 4-Hydroxynonenal: A membrane lipid oxidation product of medicinal interest. Med. Res. Rev. 2008, 28, 569-631. (Pubitemid 351842143)
39. 1H NMR study FEBS Letters 1994 355 1 81-90 (39) Claxson, A. W. D.; Hawkes, G. E.; Richardson, D. P.; Naughton, D. P.; Haywood, R. M.; Chander, C. L.; Atherton, M.; Lynch, E. J.; Grootveld, M. C. Generation of lipid peroxidation products in culinary oils and fats during episodes of thermal stressing: A high field 1H NMR study. FEBS Lett. 1994, 355, 81-90. (Pubitemid 124011924)
40. Seppanen C.M. Csallany A.S. Simultaneous determination of lipophilic aldehydes by high-performance liquid chromatography in vegetable oil JAOCS, Journal of the American Oil Chemists' Society 2001 78 12 1253-1260 J9992 (40) Seppanen, C. M.; Csallany, A. S. Simultaneous determination of lipophilic aldehydes by high-performance liquid chromatography in vegetable oil. J. Am. Oil Chem. Soc. 2001, 78, 1253-1260. (Pubitemid 34180241)
41. Seppanen, C. M.; Csallany, A. S. Formation of 4-hydroxynonenal, a toxic aldehyde, in soybean oil at frying temperature. J. Am. Oil Chem. Soc. 2002, 79, 1033-1038.
42. Seppanen, C. M.; Csallany, A. S. Incorporation of the toxic aldehyde 4-hydroxy-2-trans-nonenal into food fried in thermally oxidized soybean oil. J. Am. Oil Chem. Soc. 2004, 81, 1137-1141.
43. Han, I. H.; Csallany, A. S. Temperature dependence of HNE formation in vegetable oils and butter oil. J. Am. Oil Chem. Soc. 2008, 55, 777-782.
44. Andrikopoulos, N. K.; Chiou, A.; Mylona, A.; Boskou, G.; Dedoussis, G. V. Z. Monitoring of 2,4-decadienal in oils and fats used for frying in restaurants in Athens, Greece. Eur. J. Lipid Sci. Technol. 2004, 106, 671-679.