Effect of heating and frying on oil and food fatty acids

Fatty Acids in Foods and their Health Implications, Third Edition

Volumn , Issue , 2007, Pages 511-543

  Sánchez Muniz, Francisco J ^a   Bastida, Sara ^b   Márquez Ruiz, Gloria ^b   Dobarganes, Carmen ^c  

^a UNIVERSIDAD COMPLUTENSE DE MADRID   (Spain)

^b INSTITUTO DEL FRÍO CSIC   (Spain)

^c INSTITUTO DE LA GRASA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

CHOLESTEROL; GENE EXPRESSION; LINOLEIC ACID; LIPOPROTEINS; METABOLISM; MICELLES; MOLECULES; NUTRITION; PHOSPHOLIPIDS; SATURATED FATTY ACIDS; THERMAL PROCESSING (FOODS); TISSUE; VEGETABLE OILS;

BIOACTIVE MOLECULES; CELLULAR MEMBRANES; LIPOPROTEIN METABOLISM; LONG CHAIN FATTY ACID; MEMBRANE PHOSPHOLIPIDS; METABOLIC ENERGY; METABOLIC REGULATIONS; SOLUBLE COMPOUNDS;

UNSATURATED FATTY ACIDS;

EID: 67349159115     PISSN: None     EISSN: None     Source Type: Book    
DOI: None     Document Type: Chapter

References (173)

1. Abidi, S.L., and Rennick, K.A., Determination of non volatile components in polar fractions of rice bran oils, J. Am. Oil Chem. Soc., 80, 1057, 2003.
2. Abidi, S.L., and Warner, K.J., Molecular-weight distributions of degradation products in selected frying oils, J. Am. Oil Chem. Soc., 78, 763, 2001.
3. Abidi, S.L., Kim, I.H., and Rennick, K.A., Determination of non volatile components of heated soybean oils separated with high-efficiency mixed-bed polystyrene/divinylbenzene columns, J. Am. Oil Chem. Soc., 76, 939, 1999.
4. Ackman, R.G., Hooper, S.N., and Hooper, D.L., Linolenic acid artefacts from the deodorization of oils, J. Am. Oil Chem. Soc., 51, 42, 1974.
5. Arroyo, R., Cuesta, C., Sánchez-Montero, J.M. et al., High performance size exclusion chromatography of palm olein used for frying, Fat Sci. Technol., 95, 292, 1995.
6. Barrera-Arellano, D., Ruiz-Méndez, M.V., Márquez-Ruiz, G. et al., Loss of tocopherols and formation of degradation compounds in triacylglycerol model systems heated at high temperature, J. Sci. Food Agric., 79, 1923, 1999.
7. Barrera-Arellano, D., Ruiz-Méndez, M.V., Velasco, J. et al., Loss of tocopherols and formation of degradation compounds at frying temperatures in oils differing in degree of unsaturation and natural antioxidant content, J. Sci. Food Agric., 82, 1696, 2002.
8. Bastida, S., and Sánchez-Muniz, F.J., Selección del aceite en la fritura de los alimentos. Desde el aceite de olive a los nuevos aceites, Revista Nutrición Práctica, 5, 67, 2001a.
9. Bastida, S., and Sánchez-Muniz, F.J., Polar content vs. TAG oligomer content in the frying-life assessment of monounsaturated and polyunsaturated oils used in deep-frying, J. Am. Oil Chem. Soc., 79, 447, 2001b.
10. Bastida, S., Sánchez-Muniz, F.J., and Trigueros, G., Aplicación de un test colorimétrico al estudio del rendimiento y vida útil en fritura de alimentos precocinados y frescos en aceite de oliva, aceite de girasol y su mezcla, Grasas y Aceites, 54, 32, 2003.
11. Beatriz, M., Oliveira, P.P., and Ferreira, M.A., Evolution of the quality of the oil and the product in semi-industrial frying, Grasas y Aceites, 45, 113, 1994.
12. Berdeaux, O., Márquez-Ruiz, G., and Dobarganes, M.C., Selection of methylation procedures for quantitation of short-chain glycerol-bound compounds formed during thermoxidation, J. Chromatogr. A, 863, 171, 1999a.
13. Berdeaux, O., Márquez-Ruiz, G., and Dobarganes, M.C., Characterization, quantitation and evolution of monoepoxy compounds formed in model systems of fatty acid methyl esters and monoacid triglycerides heated at high temperature, Grasas y Aceites, 50, 53, 1999b.
14. Berdeaux, O., Velasco, J., Márquez-Ruiz, G. et al., Evolution of short-chain glycerol-bound compounds in fatty acid methyl esters and monoacid triacylglycerols during thermoxidation, J. Am. Oil Chem. Soc., 79, 279, 2002.
15. Blumenthal, M.M., and Stier, R.F., Optimization of deep-fat frying operation, Trends Food Sci. Technol., 2, 144, 1991.
16. Bognár, A., Comparative study of frying to other cooking techniques. Influence on the nutritive value, Grasas y Aceites, 49, 250, 1998.
17. Boon, P.E., de Mul, A., van der Voet, H. et al., Calculations of dietary exposure to acrylamide, Mutation Res., 580, 143, 2005.
18. Brewer, M.S., Vega, J.D., and Perkins, E.G., Volatile compounds and sensory characteristics of frying fats, J. Food Lipids, 6, 47, 1999.
19. Buckley, D.J., Zabik, J.M., Gray, J.I. et al., N-Nitrosamine formation in Irish hand US vacon as influenced by sodium nitrite concentration and the presence of α-tocopherol, Irish J. Process. Preserv., 13, 109, 1989.
20. Capella, P., Les produits de l’evolution des hydroperoxydes, Rev. Fr. Corps Gras., 36, 313, 1989.
21. Caponio, F., Pasqualone, A., and Gomes, T., Effects of conventional and microwave heating on the degradation of olive oil, Eur. Food Res. Technol., 215, 114, 2002.
22. Chang, S.S., Peterson, R.J., and Ho, C., Chemical reactions involved in the deep-fat frying of foods, J. Am. Oil Chem. Soc., 55, 718, 1978.
23. Christie, W.W., Brechany, E.Y., Sebedio, J.L. et al., Silver ion chromatography and gas chromatography-mass spectrometry in the structural analysis of cyclic monoenoic acids formed in frying oils, Chem. Phys. Lipids, 66, 143, 1993.
24. Christopoulou, C.N., and Perkins, E.G., Isolation and characterization of dimers formed in used soybean oil, J. Am. Oil Chem. Soc., 66, 1360, 1989a.
25. Christopoulou, C.N., and Perkins, E.G., Dimer acids: synthesis and mass spectrometry of the tetrahydroxy, dihydroxy, and diketo dimers of methyl stearate, J. Am. Oil Chem. Soc., 66, 1344, 1989b.
26. Christopoulou, C.N., and Perkins, E.G., Chromatographic studies on fatty acid dimers: gas liquid chromatography, high performance chromatography and thin-layer chromatography, J. Am. Oil Chem. Soc., 66, 1353, 1989c.
27. Cuesta, C., and Sánchez-Muniz, F.J., Quality control during repeated frying, Grasas y Aceites, 49, 310, 1998.
28. Cuesta, C., and Sánchez-Muniz, F.J., La fritura de los alimentos. Fritura en aceite de oliva y aceite de olive virgen extra. In Aceite de Oliva Virgen: Nuestro Patrimonio Alimentario, Vol. 1, Mataix, J., eds., Universidad de Granada and Puleva Food, Instituto Omega 3, Granada, 2001, p. 173.
29. Cuesta, C., Sánchez-Muniz, F.J., and Hernández, I., Evaluation of nonpolar methyl esters by column and gas chromatography for the assessment of used frying oils, J. Am. Oil Chem. Soc., 68, 443, 1991.
30. Cuesta, C., Sánchez-Muniz, F.J., and Varela, G., Nutritive value of frying fats. In Frying of Foods. Principles, Changes, New Approaches, Varela, G., Bender, A.E., and Morton, I.D., eds., Ellis Horwood Ltd., chichester, U.K., 1988, p. 112.
31. Cuesta, C., Sánchez-Muniz, F.J., Garrido-Polonio, C. et al., Thermoxidative and hydrolytic changes in sunflower oil used in frying with a fast turnover of fresh oil, J. Am. Oil Chem. Soc., 70, 1069, 1993.
32. Cuesta, C., Rodenas, S., Merinero, M.C. et al., Lipoprotein profile and serum peroxide levels of aged women consuming palm olein or oleic acid-rich sunflower oil diets, Eur. J. Clin. Nutr., 52, 675, 1998.
33. Cuesta, C., Romero, A., and Sánchez-Muniz, F.J., Fatty acids changes in high oleic acid sunflower oil during successive deep-fat frying of frozen foods, Food Sci. Tech. Int., 7, 317, 2001.
34. De Lorgeril, M., Salen, P., Martin, J.L. et al., Mediterranean diet, traditional risk factors, and the rate of cardiovascular complications after myocardial infarction—Final report of the Lyon Diet Heart Study, Circulation, 99, 779, 1999.
35. DGF (German Society for Fat Research), Proceedings of the 3rd international symposium of deep-fat frying. Final recommendations, Eur. J. Lipid Sci. Technol., 102, 594, 2000.
36. Devinat, G., Scamaroni, L., and Naudet, M., Isomerization of linolenic acid during the deodorization of rapeseed and soybean oils, Rev. Fr. Corps Gras, 27, 283, 1980.
37. Dietschy, J.M., Dietary fatty acids and the regulation of plasma low density lipoprotein cholesterol concentrations, J. Nutr., 128, 444S, 1998.
38. Dobarganes, M.C., Formation and analysis of high-molecular weight compounds in frying fats and oils, OCL, 5, 41, 1998.
39. Dobarganes, M.C., and Márquez-Ruiz, G., Regulation of used fats and validity of quick tests for discarding the fats, Grasas y Aceites, 49, 331, 1998.
40. Dobarganes, M.C., and Márquez-Ruiz, G., Oxidized fats in foods, Curr. Opin. Clin. Nutr. Metabol. Care, 6, 157, 2003.
41. Dobarganes, M.C., Márquez-Ruiz, G., and Pérez-Camino, M.C., Thermal stability and frying performance of genetically modified sunflower seed (Helianthus annuus L.) oils, J. Agric. Food Chem., 41, 678, 1993.
42. Dobarganes, M.C., and Pérez-Camino, M.C., Métodos analíticos de aplicación en grasas calentadas. III. Evolución de los ácidos grasos e influencia de su posición en la molécula de triglicéridos, Grasas yAceites, 36, 186, 1985.
43. Dobarganes, M.C., and Pérez-Camino, M.C., Non-polar dimer formation during thermoxidation of edible fats, Fat Sci. Technol., 89, 216, 1987.
44. Dobarganes, M.C., and Pérez-Camino, M.C., Fatty acid composition: A useful tool for the determination of alteration level in heated fats, Rev. Fr. Corps Gras, 35, 67, 1988a.
45. Dobarganes, M.C., and Pérez-Camino, M.C., Systematic evaluation of heated fats based on quantitative analytical methods, J. Am. Oil Chem. Soc., 65, 101, 1988b.
46. Dobarganes, M.C., Pérez-Camino, M.C., and Gutiérrez González-Quijano, R., Métodos analíticos de aplicación en grasas calentadas. I. Determinación de ésteres metílicos no alterados, Grasas y Aceites, 35, 172, 1984a.
47. Dobarganes, M.C., Pérez-Camino, M.C., and Ríos, J.J., Métodos analíticos de aplicación en grasas calentadas. II. Determinación de ésteres metílicos de dímeros no polares, Grasas y Aceites, 35, 351, 1984b.
48. Dobarganes, M.C., Pérez-Camino, M.C., and Márquez-Ruiz, G., High performance size exclusion chromatography of polar compounds in heated a non-heated fats, Fat Sci. Technol., 90, 308, 1988.
49. Dobarganes, M.C., Velasco, J., Márquez-Ruiz, G. et al., Determination of oxidation compounds and oligomers by chromatographic techniques. In Frying of Food. Oxidation, Nutrient and Non-Nutrient Antioxidants, Biologically Active Compounds and High Temperatures, Boskou, D. and Elmadfa, I., eds, Technomic Publishing Co. Inc., Lancaster, PA, 1999, p. 143.
50. Dobarganes, M.C., Velasco, J., and Dieffenbacher, A., The determination of polar compounds, polymerised triacylglycerols, oxidised triacylglycerols and diacylglycerols in fats and oils, Pure Appl. Chem., 72, 1563, 2000a.
51. Dobarganes, M.C., Márquez-Ruiz, G., and Velasco, J., Interactions between fat and food during deep frying, Eur. J. Lipid Sci. Technol., 102, 521, 2000b.
52. Dobson, G., Christie, W.W., Brechany, E.Y. et al., Silver ion chromatography and gas chromatography-mass spectrometry in the structural analysis of cyclic dienoic acids formed in frying oils, Chem. Phys. Lipids, 75, 171, 1995.
53. Elmadfa, I., and Wagner, K.-H., Fat and Nutrition. In Frying of Food. Oxidation, Nutrient and Non-Nutrient Antioxidants, Biologically Active Compounds and High Temperatures, Boskou, D. and Elmadfa, I., eds., Technomic Publishing Co. Inc., Lancaster, PA, 1999, p. 1.
54. Fedelli, E., Gasparoli, A., and Daghetta, A., Changes in vegetable oils induced by heating in presence of air. VI. Interactions between olive oil and soybean triglycerides and starch, Riv. Ital. Sost. Gr., 60, 257, 1983.
55. Figge, K., Dimeric fatty acid [1-14C] methyl esters. I. Mechanisms and products of thermal and oxidativethermal reactions of unsaturated fatty acid esters—Literature review, Chem. Phys. Lipids, 6, 164, 1971a.
56. Figge, K., Dimeric fatty acids [1-14C] methyl esters. 2. Preparation and rate of formation; thermal polymerization of monomers, Chem. Phys. Lipids, 6, 178, 1971b.
57. Firestone, D., Regulation of frying fat and oil. In Deep Frying. Chemistry, Nutrition, and Practical Applications, Perkins, E.G. and Erickson, M.D., eds., AOCS Press, Champaign, IL, 1996, p. 323.
58. Fillon, L., and Henry, C.J.K., Nutrient losses and gain during frying, Int. J. Food Sci. Nutr., 49, 157, 1998.
59. Frankel, E.N., Review. Recent advances in lipid oxidation, J. Sci. Food Agric., 54, 495, 1991.
60. Frankel, E.N., Lipid Oxidation, 2nd ed., The Oily Press, Dundee, U.K., 2005.
61. Gall, K.L., Otwell, W.S., Koburger, J.A. et al., Effects of four cooking methods on the proximate mineral and fatty acid composition of fish fillets, J. Food Sci., 48, 1068, 1983.
62. Gamel, T.H., Kiritsakis, A., and Petrakis, C., Effect of phenolic extracts on trans fatty acid formation during frying, Grasas y Aceites, 50, 421, 1999.
63. García-Arias, M.T., García-Linares, M.C., Capita, R. et al., Deep-frying of chicken meat and chicken-based product. Changes in the proximate and fatty acid compositions, Ital. J. Food Sci., 15, 225, 2003.
64. García-Arias, M.T., Pontes, E.A., Linares, M.C.G. et al., Cooking–freezing–reheating (CFR) of sardine (Sardina pilchardus) fillets. Effect of different cooking and reheating procedures on the proximate and fatty acid compositions, Food Chem., 83, 349, 2003.
65. García-Ayuso, L.E., Velasco, J., Dobarganes, M.C. et al., Determination of the oil content in seeds by focused microwave-assisted söxhlet extraction, Chromatographia, 52, 103, 2000.
66. Garrido-Polonio, M.C., Sánchez-Muniz, F.J., Arroyo, R. et al., Small scale frying of potatoes in sunflower oil: Thermoxidative alteration of the fat content in the fried product, Z. Ernährungswiss., 33, 267, 1994.
67. Garrido-Polonio, M.C., García-Linares, M.C., García-Arias, M.T. et al., Thermal oxidized sunflower oil increases liver and serum peroxides and modifies lipoprotein composition in rats, Br. J. Nutr., 92, 257, 2004.
68. González-Muñoz, M.J., Bastida, S., and Sánchez-Muniz, F.J., Short-term in vivo digestibility of triglyceride polymers, dimers and monomers of thermoxidized palm olein used in deep-frying, J. Agric. Food Chem., 46, 5188, 1998.
69. González-Muñoz, M.J., Bastida, S., and Sánchez-Muniz, F.J., Column and high-performance size exclusion chromatography applications to the in vivo digestibility study of a thermoxidized and polymerized olive oil, Lipids, 34, 1187, 1999.
70. González-Muñoz, M.J., Bastida, S., and Sánchez-Muniz, F.J., Short term in vivo digestibility of a highly oxidised and polymerised sunflower oil, J. Sci. Food Agric., 83, 413, 2003.
71. Grandgirard, A., Sébédio, J.L., and Fleury, J., Geometrical isomerization of linolenic acid during heat treatment of vegetable oils, J. Am. Oil Chem. Soc., 61, 1563, 1984.
72. Hamilton, R.J., and Perkins, E.G., Chemistry of deep fat frying. In New Developments in Iindustrial Frying, Kochhar, S.P., ed., PJ Barnes & Associates, Bridgwater, U.K., 1997.
73. Henry, C.J.K., Impact of fried of fried foods on macronutrient intake, with special reference to fat and protein, Grasas y Aceites, 49, 336, 1998.
74. Houhoula, D.P., Oreopoulou, V., and Tzia, C., The effect of process time and temperature on the accumulation of polar compounds in cottonseed oil during deep-fat frying, J. Sci. Food Agric., 83, 314, 2003.
75. IUPAC, Standard method 2.507: Determination of polar compounds in frying fats. In Standard Method for the Analysis of Oils, Fats and Derivatives, 1st Supplement to the 7th edition, International Union of Pureand Applied Chemistry, ed., Blackwell, Oxford, U.K., 1992a.
76. UPAC, Standard method 2.508, Determination of polymerized triglycerides in oils and fats by high performance liquid chromatography. In Standard Method for the Analysis of Oils, Fats and Derivatives, 1st Supplement to the 7th edition. International Union of Pure and Applied Chemistry, ed., Blackwell, Oxford, U.K., 1992b.
77. Iwaoka, W.T., and Perkins, E.G., Metabolism and lipogenic effect of the cyclic monomers of methyl linolenate in the rat, J. Am. Oil Chem. Soc., 55, 734, 1978.
78. Jorge, N., Márquez-Ruiz, G., Martín-Polvillo, M. et al., Influence of dimethylpolysiloxane addition to frying oils: Performance of sunflower oil in discontinuous and continuous laboratory frying, Grasas y Aceites, 47, 20, 1996a.
79. Jorge, N., Márquez-Ruiz, G., Martín-Polvillo, M. et al., Influence of dimethylpolysiloxane addition to edible oils: Dependence on the main variables of the frying process, Grasas y Aceites, 47, 14, 1996b.
80. Jump, D.B., Fatty acid regulation of gene transcription, Crit. Rev. Clin. Lab. Sci., 41, 41, 2004.
81. Kamal-Eldin, A., and Appelqvist, L.A., Aldehydic acids in frying oils: Formation, toxicological significance and analysis, Grasas y Aceites, 47, 342, 1996.
82. Kamal-Eldin, A., Márquez-Ruiz, G., Dobarganes, M.C. et al., Characterization of aldehydic acids in used and unused frying oils, J. Chromatogr. A, 776, 245, 1997.
83. Kamal-Eldin, A., Velasco, J., and Dobarganes, M.C., Oxidation of mixtures of triolein and trilinolein at elevated temperatures, Eur. J. Lipid Sci. Technol., 105, 165, 2003.
84. Kanazawa, K., and Ashida, H., Target enzymes on hepatic dysfunction caused by dietary products of lipid peroxidation, Arch. Biochem. Biophys., 288, 71, 1991.
85. Keys, A., Menotty, A., Karvonen, M.J. et al., The diet and 15-year death rate in the seven countries study, Am. J. Epidemiol., 124, 903, 1986.
86. Kris-Etherton, P.M., AHA Science Advisory monounsaturated fatty acids and risk of cardiovascular disease. American Heart Association. Nutrition Committee, Circulation, 100, 1253, 1999.
87. Lambert, C.R., Formation of free radicals and protection mechanisms in vitro and in vivo. In Frying of Food. Oxidation, Nutrient and Non-Nutrient Antioxidants, Biologically Active Compounds and High Temperatures, Boskou, D. and Elmadfa, I., eds., Technomic Publishing Co. Inc., Lancaster, PA,1999, p. 47.
88. Le Quéré, J.L., and Sébédio, J.L., Cyclic monomers of fatty acids. In Deep Frying. Chemistry, Nutrition, and Practical Applications, Perkins, E.G. and Erickson, M.D., eds., AOCS Press, Champaign, IL, 1996, p. 49.
89. López-Varela, S., Sánchez-Muniz, F.J., and Cuesta, C., Decrease food efficiency ratio, growth retardation and changes in liver composition in rats consuming thermoxidized and polymerized sunflower oil used for frying, Food Chem. Toxicol., 33, 181, 1995.
90. Luque-García, J.L., Velasco, J., Dobarganes, M.C. et al., Fast quality monitoring of oil from prefried and fried foods by focused microwave-assisted Söxhlet extraction, Food Chem., 76, 241, 2002.
91. Mahungu, S.M., Artz, W.E., and Perkins, E.G., Oxidation products and metabolic processes. In Frying of Food. Oxidation, Nutrient and Non-Nutrient Antioxidants, Biologically Active Compounds and High Temperatures, Boskou, D. and Elmadfa, I., eds., Technomic Publishing Co. Inc., Lancaster, PA, 1999, p. 183.
92. Makinson, J.H., Green-Deld, H., Wong, M.L. et al., Fat uptake during deep-fat frying of coated and uncoated foods, J. Food Comp. Anal., 1, 93, 1987.
93. Marmesat, S., Velasco, J., Ruiz Méndez M.V. et al., Performance of sunflower oil with high levels of oleic and palmitic acids during industrial frying of almonds, peanuts and sunflower seeds, J. Am. Oil Chem. Soc., 82, 505, 2005.
94. Márquez-Ruiz, G., and Dobarganes, M.C., Assessments on the digestibility of oxidized compounds from [1-14C]-linoleic acid using a combination of chromatographic techniques, J. Chromatogr. B, 675, 1, 1995.
95. Márquez-Ruiz, G., and Dobarganes, M.C., Short-chain acid formation during thermoxidation and frying, J. Sci. Food Agric., 70, 120, 1996.
96. Márquez-Ruiz, G., and Dobarganes, M.C., Nutritional and physiological effects of used frying oils and fats. In Deep Frying. Chemistry, Nutrition and Practical Applications, 2nd ed., Erickson, M.D., ed., AOCS Press, Champaign, IL, 2006, p. 177.
97. Márquez-Ruiz, G., Pérez-Camino, M.C., and Dobarganes, M.C., Combination of adsorption and size-exclusion chromatography for the determination of fatty acid monomers, dimers and polymers, J. Chromatogr. A, 514, 37, 1990.
98. Márquez-Ruiz, G., Pérez-Camino, M.C., and Dobarganes, M.C., In vitro action of lipase on complex glycerides from thermally oxidized oils, Fat Sci. Technol., 94, 307, 1992.
99. Márquez-Ruiz, G., Pérez-Camino, M.C., and Dobarganes, M.C., Evaluation of hydrolysis and absorption of thermally oxidized olive oil in non-absorbed lipids in the rat, Ann. Nutr. Metab., 37, 121, 1993.
100. Márquez-Ruiz, G., Tasioula-Margari, M., and Dobarganes, M.C., Quantitation and distribution of altered fatty acids in frying fats, J. Am. Oil Chem. Soc., 72, 1171, 1995.
101. Márquez-Ruiz, G., Jorge, N., Martín-Polvillo, M. et al., Rapid, quantitative determination of polar compounds in fats and oils by solid-phase extraction and exclusion chromatography using monostearin as internal standard, J. Chromatogr. A, 749, 55, 1996.
102. Márquez-Ruiz, G., Garcés, R., León-Camacho, M. et al., Thermoxidative stability of triacylglycerols from mutant sunflower seeds, J. Am. Oil Chem. Soc., 76, 1169, 1999.
103. Massaro, M., Basta, G., Lazzerini, G. et al., Quenching of intracellular ROS generation as a mechanism for oleate-induced reduction of endothelial activation and early atherogenesis, Thromb. Haemost., 88, 335, 2002.
104. Massaro, M., Scoditti, E., Carluccio, M.A. et al., Epidemiology of olive oil and cardiovascular disease. In Olive Oil and Health, Quiles, J.L., Ramírez-Tortosa, M.C., and Yaqoob, P., eds., CABI. Org., Oxfordshire, U.K., 2006, p. 152.
105. Masson, L., Robert, P., Romero, N. et al., Comportamiento de aceites poliinsaturados en la preparación de patatas fritas para consumo inmediato: Formación de nuevos compuestos y comparación de métodos analíticos, Grasas y Aceites, 48, 273, 1997.
106. Masson, L., Robert, P., Izaurieta, M. et al., Fat deterioration in deep fat frying of French fries potatoes at restaurant and food shop sector, Grasas y Aceites, 50, 460, 1999.
107. Masson, L., Robert, P., Dobarganes, M.C. et al., Stability of potato chips fried in vegetable oils with different degree of unsaturation. Effect of ascorbyl palmitate during storage, Grasas y Aceites, 53, 190, 2002.
108. Mata, P., Alonso, R., and Mata, N., Los omega-3 y omega-9 en la enfermedad cardiovascular. In Libro blanco de los omega-3. Los ácidos grasos poliinsaturados omega 3 y monoinsaturados tipo oleico y su papel en la salud, Mataix, J. and Gil, A., Coordinators, Instituto Omega 3, Puleva Food, Madrid,2002, p. 50.
109. May, J., Shimp, J., Weirhauch, J. et al., Lipids of fish fillets: Changes following cooking by different methods, J. Food Sci., 43, 1669, 1978.
110. Mensink, R.P., and Katan, M.B., Effect of dietary fatty acids on serum lipids and lipoproteins: A meta-analysis on 27 trials, Arterioscler. Thromb., 12, 911, 1992.
111. Minamoto, S., Kanazawa, K., Ashida, H. et al., Effect of orally administered 9-oxononanoic acid on lipogenesis in rat liver, Biochim. Biophys. Acta, 958, 199, 1988.
112. Monferrer, A., and Villalta, J., La fritura desde un punto de vista práctico. I, Alimentación, equipos y Tecnología, abril, 87, 1993.
113. Mossoba, M.M., Yurawecz, M.P., Roach, J.A.G. et al., Rapid determination of double bond configuration and position along the hydrocarbon chain in cyclic fatty acid monomers, Lipids, 29, 893, 1994.
114. Nawar, W.W., Chemical changes in lipids produced by thermal processing, J. Chem. Edu., 61, 299, 1984.
115. Neff, W.E., and Byrdwell, W.C., Characterization of model triacylglycerol (triolein, trilinolein and trilinolenin) autoxidation products via high-performance liquid chromatography coupled with atmospheric pressure chemical ionization mass spectrometry, J. Chromatogr. A, 818, 169, 1998.
116. Ottaviani, P., Graille, J., Perfetti, P. et al., Produits d’alteration thermoxydative des huiles chauffees II. Composes apolaires ou faiblement polaires, Chem. Phys. Lipids, 24, 57, 1979.
117. Pantzaris, T.P., Palm oil in frying. In Frying of Food. Oxidation, Nutrient and Non-Nutrient Antioxidants, Biologically Active Compounds and High Temperatures, Boskou, D. and Elmadfa, I., eds., TechnomicPublishing Co. Inc., Lancaster, PA, 1999, p. 223.
118. Peers, K.E., and Swoboda, A.T., Deterioration of sunflower seed oil under simulated frying conditions and during small-scale frying of potato chips, J. Sci. Food Agric., 33, 389, 1982.
119. Pérez-Camino, M.C., Márquez-Ruíz, G., Ruíz-Méndez, M.V. et al., Lipid changes during frying of frozen prefried foods, J. Food Sci., 56, 1644, 1991.
120. Perkins, E.G., and Kummerow, F.A., The isolation and characterization of the polymers formed during the thermal oxidation of corn oil, J. Am. Oil Chem. Soc., 36, 371, 1959.
121. Perkins, E.G., Taubold, R., and Hsieh, A., Gel-permeation chromatography of heated fats, J. Am. Oil Chem. Soc., 50, 223, 1973.
122. Perrin, J.L., Redero, F., and Prevot, A., Dosage rapide des polymères de triglycérides par chromatographie d’exclusion, Rev. Fr. Corps Gras, 31, 131, 1984.
123. Perrin, J.L., Perfetti, P., Dimitriades, C. et al., Etude analytique approfondie d’huiles chauffées I. Techniques analytiques et essais préliminaires, Rev. Fr. Corps Gras, 32, 151, 1985.
124. Pokorný, J., Effect of browning reactions on the formation of flavor substances, Nahrung, 24, 115, 1980.
125. Pokorný, J., Substrate influence on the frying process, Grasas y Aceites, 49, 2265, 1998.
126. Pokorný, J., Changes of nutrients at frying temperatures. In Frying of Food. Oxidation, Nutrient and Non-Nutrient Antioxidants, Biologically Active Compounds and High Temperatures, Boskou, D. and Edmalfa, I., eds., Technomic Publishing Co. Inc., Lancaster, PA, 1999, p. 69.
127. Porter, N.A., Cadwell, S.E., and Mills, K.A., Mechanisms of free radical oxidation of unsaturated lipids, Lipids, 30, 277, 1995.
128. Pozo-Díaz, R.M., Masoud Musa, T.A., Pérez-Camino, M.C. et al., Intercambio lipídico durante la fritura de patatas prefritas congeladas en aceite de girasol alto oleico, Grasas y Aceites, 46, 85, 1995.
129. Ramanna, B.R., and Sen, D.P., Influence of water on the changes during heating of oils, J. Food Sci. Technol. India, 20, 146, 1983.
130. Romero, A., Bastida, S., and Sánchez-Muniz, F.J., Cyclic fatty acid monomer formation in domestic frying of frozen foods in sunflower oil and high oleic acid sunflower oil without oil replenishment, Food Chem. Toxicol., 44, 1674, 2006.
131. Romero, A., Bastida, S., and Sánchez-Muniz, F.J., Cyclic fatty acids in sunflower oils during frying of frozen foods with oil replenishment. Eur. J. Lipid Sci. Technol., 109, 165, 2007.
132. Romero, A., Cuesta, C., and Sánchez-Muniz, F.J., Quantitation and distribution of polar compounds in an extra virgin olive oil used in fryings with turnover of fresh oil, Fett Wissens. Technol., 97, 403, 1995.
133. Romero, A., Cuesta, C., and Sánchez-Muniz, F.J., Effect of oil replenishment during deep-fat frying of frozen foods in sunflower oil and high-oleic acid sunflower oil, J. Am. Oil Chem. Soc., 75, 161, 1998.
134. Romero, A., Sánchez-Muniz, F.J., and Cuesta, C., Does frequent replenishment with fresh oil permit the frying of potatoes indefinitely? J. Agric. Food Chem., 47, 1168, 1999.
135. Romero, A., Cuesta, C., and Sánchez-Muniz, F.J., Trans fatty acid production in deep fat frying of frozen foods with different oils and frying modalities, Nutr. Res., 20, 599, 2000a.
136. Romero, A., Sánchez-Muniz, F.J., and Cuesta, C. Deep fat frying of frozen foods in sunflower oil. Fatty acid composition in fryer oil and frozen prefried potatoes, J. Sci. Food. Agric., 80, 2135, 2000b.
137. Romero, A., Cuesta, C., and Sánchez-Muniz, F.J., Cyclic fatty acid monomers in high-oleic acid sunflower oil and extra virgin olive oil used in repeated frying of fresh potatoes, J. Am. Oil Chem. Soc., 80, 437, 2003.
138. Ros, E., Guía para una alimentación cardiosaludable. Aporte de grasa. In Guías Alimentarias para la población Española. Recomendaciones para una dieta saludable, Sociedad Española de la NutriciónComunitaria, ed., IM&C, S.A., Madrid, 2001, p. 413.
139. Sánchez-Muniz, F.J., and Bastida, S., Ácidos grasos omega-3 y protección cardiovascular. Consideraciones sobre su consumo y recomendaciones para la población española, Rev. Nutr. Práctica, 1, 123, 1997.
140. Sánchez-Muniz, F.J., and Bastida, S., Frying oil discarding: Polar content vs. oligomer content determination, Forum Nutr., 56, 345, 2003.
141. Sánchez-Muniz, F.J., and Bastida, S., Effect of frying and thermal oxidation on olive oil and food quality. In Olive Oil and Health, Quiles, J.L., Ramírez-Tortosa, M.C., and Yaqoob, P., eds., CABI. Org., Oxfordshire, U.K., 2006, p. 74.
142. Sánchez-Muniz, F.J., and Sánchez-Montero, J.M., Enzymatic methods for the study of thermally oxidized oils and fats. In Frying of food. Oxidation, nutrient and non-nutrient antioxidants, biologically activecompounds and high temperatures, Boskou, D. and Elmadfa, I., eds., Technomic Publishing Co. Inc., Lancaster, PA, 1999, p. 105.
143. Sánchez-Muniz, F.J., Medina, R., Higón, E. et al., Aceites de oliva y girasol y manteca de cerdo en frituras repetidas de sardinas. Valoración del rendimiento y grado de alteración, Grasas y Aceites, 41, 256, 1990.
144. Sánchez-Muniz, F.J., Viejo, J.M., and Medina, R., Deep-frying of sardines in different culinary fats. Changes in the fatty acid composition of sardines and frying fats, J. Agric. Food Chem., 40, 2252, 1992a.
145. Sánchez-Muniz, F.J., Higón, E., Cava, F. et al., Prevention of dietary hypercholesterolemia in rats using sunflower-oil-fried sardines. Effects on cholesterol and serum enzymes, J. Agric. Food Chem., 40, 2226, 1992b.
146. Sánchez-Muniz, F.J., Cuesta, C., and Garrido-Polonio, M.C., Sunflower oil used for frying. Combination of column, gas and high-performance size-exclusion chromatography for its evaluation, J. Am. Oil Chem. Soc., 70, 235, 1993.
147. Sánchez-Muniz, F.J., Cava, F., Viejo, J.M. et al., Olive oil-fried sardines in the Prevention of dietary hypercholesterolemia in rats. Effects on some serum lipids and cell-damage marker enzymes, Nutr. Res., 16, 111, 1996.
148. Sánchez-Muniz, F.J., García-Linares, M.C., García-Arias, M.T. et al., Fat and protein from olive oil fried sardines interact to normalize serum lipoproteins and liver lipids in hypercholesterolemic rats, J. Nutr., 133, 2302, 2003.
149. Sébédio, J.L., and Chardigny, J.-M., Physiological effects of trans and cyclic fatty acids. In Deep frying. Chemistry, nutrition, and practical applications, Perkins, E.G. and Erickson, M.D., eds., AOCS Press, Champaign, IL, 1996, p. 183.
150. Sébédio, J.L., and Grandgirard, A., Cyclic fatty acids: Natural sources, formation during heat treatment, synthesis and biological properties, Prog. Lipid Res., 28, 303, 1989.
151. Sébédio, J.L., Prevost, J., and Grandgirard, A., Heat treatment of vegetable oils I. Isolation of the cyclic fatty acid monomers from heated sunflower and linseed oils, J. Am. Oil Chem. Soc., 64, 1026, 1987.
152. Sébédio, J.L., Bonpunt, A., Grandgirard, A. et al., Deep fat frying of frozen prefried French fries: Influence of the amount of linolenic acid in the frying medium, J. Agric. Food Chem., 38, 1862, 1990.
153. Sébédio, J.L., Ratnayake, W.M.N., Ackman, R.G. et al., Stability of polyunsaturated ω-3 fatty acids during deep fat frying of Atlantic mackerel, Food Res. Int., 26, 163, 1993.
154. Sébédio, J.L., Dobarganes, M.C., Márquez-Ruiz, G. et al., Industrial production of crips and prefried French fries using sunflower oils, Grasas y Aceites, 47, 5, 1996.
155. Sen Gupta, A.K., Untersuchungen über die struktur dimerer fettsäuren. V. Thermische und peroxidkatalsierte dimerisierung von linolensäure-methylester, Fette Seifen Anstrichm., 71, 873, 1969.
156. Skjöldebrand, C., Introduction to process group A (Frying, grilling, boiling). In Thermal Processing and Quality of Foods, Varela, G., ed., Elsevier Applied Science Publisher Ltd., New York, 1984, p. 313.
157. Stevenson, S.G., Vaisey-Genser, M., and Eskin, N.A.M., Quality control in the use of deep frying oils, J. Am. Oil Chem. Soc., 61, 1102, 1984.
158. Tareke, E. et al., Analysis of acrylamide, a carcinogen formed in heated food-stuffs, J. Agric. Food Chem., 50, 4998, 2002.
159. Thomson, L.U., and Aust, R., Lipid changes in French fries and heated oils during commercial deep frying and their nutritional and toxicological implications, Can. Inst. Food Sci. Technol. J., 16, 246, 1983.
160. Tornberg, E., Olsson, A., and Persson, K., A comparison in fat holding between hamburgers and emulsion sausages, Proc. Ing. Congr. Meat Sci. Technol., 35, 752, 1989.
161. Trichopoulos, A., Costacou, T., Bamia, C. et al., Adherence to a Mediterranean diet and survival in a Greek population, N. Engl. J. Med., 348, 2599, 2003.
162. Varela, G., Current facts about the frying of food. In Frying of Food. Principles, Changes, New Approaches, Varela, G., Bender, A.E., and Morton, I.D., eds., Ellis Horwood Ltd., Chichester, U.K., 1988, p. 9.
163. Varela, G., and Ruiz-Roso, B., Influence of the frying process on the real fat intake, Grasas y Aceites, 49, 366, 1998.
164. Velasco, J., Berdeaux, O., Márquez-Ruiz, G. et al., Sensitive and accurate quantitation of monoepoxy fatty acids in thermoxidized oils by gas-liquid chromatography, J. Chromatogr. A, 982, 145, 2002.
165. Velasco, J., Marmesat, S., Bordeaux, O. et al., Formation and evolution of monoepoxy fatty acids in thermoxidized olive and sunflower oils and quantitation in used frying oils from restaurants and fried food outlets, J. Agric. Food Chem., 52, 4438, 2004a.
166. Velasco, J., Marmesat, S., Márquez-Ruiz, G. et al., Formation and occurrence of short-chain fatty acids and oxidized monomeric triglycerides during deep-frying, Eur. J. Lipid Sci. Technol., 106, 728, 2004b.
167. Velasco, J., Marmesat, S., Bordeaux, O. et al., Quantitation of short-chain glycerol-bound compounds in thermoxidized and used frying oils. A monitoring study during thermoxidation of olive and sunflower oils, J. Agric. Food Chem., 53, 4006, 2005.
168. Verleyen, T., Kamal-Eldin, A., Dobarganes, M.C. et al., Modelling of alpha-tocopherol loss and oxidation products formed during thermoxidation in triolein and tripalmitin mixtures, Lipids, 36, 719, 2001.
169. Verleyen, T., Kamal-Eldin, A., Mozuraityte, R. et al., Oxidation at elevated temperatures: Competition between alpha-tocopherol and unsaturated triacylglycerols, Eur. J. Lipid Sci. Technol., 104, 228, 2002.
170. Waltking, A.E., and Wessels, H.J., Chromatographic separation of polar and non polar components on frying fats, J. Assoc. Off. Anal. Chem., 64, 1329, 1981.
171. Wheeler, D.H., Milun, A., and Linn, F., Dimeric acid structures: Cyclic structures of clay catalized dimers of normal linoleic acid, 9-cis, 12-cis-octadecadienioc acid, J. Am. Oil Chem. Soc., 47, 242, 1970.
172. Williamson, L., The thermal decomposition of methyl linoleate hydroperoxide, J. Appl. Chem., 3, 301, 1953.
173. Zock, P., and Katan, M.B., Hydrogenation alternatives: Effects of trans fatty acids and stearic acid versus linoleic acid on serum lipids and lipoproteins in humans, J. Lipid. Res., 33, 399, 1992.