Volatile constituents of used frying oils

Journal of Agricultural and Food Chemistry

Volumn 44, Issue 3, 1996, Pages 654-660

  Takeoka, Gary ^a   Perrino Jr , Charles ^a   Buttery, Ron ^a  

^a WESTERN REGIONAL RESEARCH CENTER   (United States)

Author keywords

Deep fat frying; Frying oil; Simultaneous steam distillation extraction; Volatiles

Indexed keywords

EID: 0001650281     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf950430m     Document Type: Article

References (56)

1. Alencar, J. W.; Alves, P. B.; Craveiro, A. A. Pyrolysis of tropical vegetable oils. J. Agric. Food Chem. 1983, 31, 1268-1270.
2. Alexander, J. C. Chemical and biological properties related to toxicology of heated fats. J. Toxicol. Environ. Health 1981, 7, 125-138.
3. Alexander, J. C.; Valli, V. E.; Chanin, R. E. Biological observations from feeding heated corn oil and heated peanut oil to rats. J. Toxicol. Environ. Health 1987, 21, 295-309.
4. Ames, J. M.; Apriyatono, A. Volatile reaction products from a heated xylose-lysine model system. Food Chem. 1993, 48, 271-277.
5. Andia, A. G.; Street, J. C. Dietary induction of hepatic microsomal enzymes by thermally oxidized fats. J. Agric. Food Chem. 1975, 23, 173-177.
6. Baltes, W.; Bochmann, G. Model reactions on roast aroma formation. II. Mass spectrometric identification of furans and furanones from the reaction of serine and threonine with sucrose under the conditions of coffee roasting. Z. Lebensm. Unters. Forsch. 1987, 184, 179-186.
7. Baltes, W.; Knoch, E. Model reactions on roast aroma formation. XIII. The formation of some uncommon N-heterocyclic compounds and furans after roasting of tryptophan with reducing sugars and sugar degradation products. Food Chem. 1993, 46, 343-349.
8. Billek, G. Heated oils. Chemistry and nutritional aspects. Nutr. Metab. 1976, 24, 200-210.
9. Brown, W. H.; Sawatzky, H. The condensation of furan and Sylvan with some carbonyl compounds. Can. J. Chem. 1956, 34, 1147-1153.
10. Buttery, R. G.; Ling, L. C. Volatile components of tomato fruit and plant parts-relationship and biogenesis. In Bioactive Volatile Compounds from Plants; Teranishi, R., Buttery, R. G., Sugisawa, H., Eds.; ACS Symposium Series 525; American Chemical Society: Washington, DC, 1993; pp 23-34.
11. Buttery, R. G.; Seifert, R. M.; Guadagni, D. G.; Black, D. R.; Ling, L. C. Characterization of some volatile constituents of carrots. J. Agric. Food Chem. 1968, 16, 1009-1015.
12. 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.
13. Chung, T. Y.; Eiserich, J. P.; Shibamoto, T. Volatile compounds identified in headspace samples of peanut oil heated under temperatures ranging from 50 to 200 °C. J. Agric. Food Chem. 1993, 41, 1467-1470.
14. Clark, W. L.; Serbia, G. W. Safety aspects of frying fats and oils. Food Technol. 1991, 45, 84-89.
15. Ferretti, A.; Flanagan, V. P. The lactose-casein (Maillard) browning system: volatile components. J. Agric. Food Chem. 1971, 19, 245-249.
16. Ferretti, A.; Flanagan, V. P.; Ruth, J. M. Nonenzymatic browning in a lactose-casein model system. J. Agric. Food Chem. 1970, 18, 13-18.
17. Formacek, V.; Kubcezka, K.-H. Celery seed oil. In Essential Oil Analysis by Capillary Gas Chromatography and Carbon-13 NMR Spectroscopy; Wiley: New York, 1982; pp 37-39.
18. Furniss, B. S.; Hannaford, A. J.; Smith, P. W. G.; Tatchell, A. R. In Vogel's Textbook of Practical Organic Chemistry, 5th ed.; Longman Scientific & Technical: Essex, England, 1989; pp 827-828, 831.
19. Gardner, H. W.; Selke, E. Volatiles from thermal decomposition of isomeric methyl (12S,13S)-(E)-12,13-epoxy-9-hydroperoxy-10-octadecenoates. Lipids 1984, 19, 375-380.
20. Gassenmaier, K.; Schieberle, P. Comparison of important odorants in puff-pastries prepared with butter or margarine. Lebensm. Wiss. Technol. 1994a, 27, 282-288.
21. Gassenmaier, K.; Schieberle, P. Formation of the intense flavor compound trans-4,5-epoxy-(E)-2-decenal in thermally treated fats. J. Am. Oil Chem. Soc. 1994b, 71, 1315-1319.
22. Gilman, H.; Calloway, N. O. Super-aromatic properties of furan. II. The Friedel-Crafts reaction. J. Am. Chem. Soc. 1933, 55, 4197-4205.
23. Guth, H.; Grosch, W. 3-Methylnonane-2,4-dione - an intense odour compound formed during flavour reversion of soyabean oil. Fat Sci. Technol. 1989, 91, 225-230.
24. Guth, H.; Grosch, W. Comparison of stored soya-bean and rapeseed oils by aroma extract dilution analysis. Lebensm. Wiss. Technol. 1990, 23, 59-65.
25. Hageman, G.; Kikken, R.; Ten Hoor, F.; Kleinjans, J. Assessment of mutagenic activity of repeatedly used deep-frying fats. Mutat. Res. 1988, 204, 593-604.
26. Henderson, S. K.; Witchwoot, A.; Nawar, W. W. The autoxidation of linoleates at elevated temperatures. J. Am. Oil Chem. Soc. 1980, 57, 409-413.
27. Huopalahti, R.; Linko, R. R. Composition and content of aroma compounds in dill, Anethum graveolens L., at three different stages. J. Agric. Food Chem. 1983, 31, 331-333.
28. Konopka, U. C.; Grosch, W. Potent odorants causing the warmed-over flavour in boiled beef. Z. Lebensm. Unters. Forsch. 1991, 193, 123-125.
29. Kovats, E. sz. Gas-chromatographische charakterisierung organischer verbindungen teil 1: retentionindices aliphatischer halogenide, alcohole, aldehydeundketone. Helv. Chim. Acta 1958, 41, 1915-1932.
30. Lam, L. K. T.; Zhang, J.; Zhang, F.; Zhang, B. Inhibition of chemically induced carcinogenesis by 2-n-heptylfuran and 2-n-butylthiophene from roast beef aroma. In Sulfur Compounds in Foods; Mussinan, C., Keelan, M. E., Eds.; ACS Symposium Series 564; American Chemical Society: Washington, DC, 1994; pp 278-291.
31. Loughran, E. D.; Wewerka, E. M.; Hammons, G. J. A mass spectrometric study of substituted furfuryl compounds (1). J. Heterocycl. Chem. 1972, 9, 57-65.
32. MacGregor, J. T.; Wilson, R. E.; Neff, W. E.; Frankel, E. N. Mutagenicity tests of lipid oxidation products in Salmonella typhimurium: monohydroperoxides and secondary oxidation products of methyl linoleate and methyl linolenate. Food Chem. Toxicol. 1985, 23, 1041-1047.
33. Macku, C.; Shibamoto, T. Headspace volatile compounds formed from heated corn oil and corn oil with glycine. J. Agric. Food Chem. 1991a, 39, 1265-1269.
34. Macku, C.; Shibamoto, T. Volatile sulfur-containing compounds generated from the thermal interaction of corn oil and cysteine. J. Agric. Food Chem. 1991b, 39, 1987-1989.
35. Marnett, L. J.; Hurd, H. K.; Hollstein, M. C.; Levin, D. E.; Esterbauer, H.; Ames, B. N. Naturally occurring carbonyl compounds are mutagens in Salmonella tester strain TA104. Mutat. Res. 1984, 148, 25-34.
36. Saleh, M. A.; Ahmed, K. A.; Sharaf, A. N.; Abdel-Latif, M. S. Mutagenicity of heated cottonseed frying oil. J. Food Saf. 1986, 7, 203-213.
37. Schieberle, P. Primary odorants in popcorn. J. Agric. Food Chem. 1991, 39, 1141-1144.
38. Schieberle, P. Studies on the flavour of roasted white sesame seeds. In Progress in Flavour Precursor Studies; Schreier, P., Winterhalter, P., Eds.; Proceedings of the International Conference, Würzburg; Allured Publishing: Carol Stream, IL, 1993; pp 343-360.
39. Schieberle, P.; Grosch, W. Potent odorants of the wheat bread crumb-Differences to the crust and effect of a longer dough fermentation. Z. Lebensm. Unters. Forsch. 1991, 192, 130-135.
40. Schultz, T. H.; Flath, R. A.; Mon, T. R.; Eggling, S. B.; Teranishi, R. Isolation of volatile components from a model system. J. Agric. Food Chem. 1977, 25, 446-449.
41. Selke, E.; Rohwedder, W. K.; Dutton, H. J. Volatile compoents from trilinolein heated in air. J. Am. Oil Chem. Soc. 1980, 57, 25-30.
42. Shaath, N. A.; Griffin, P.; Dedeian, S.; Paloympis, L. The chemical composition of Egyptian parsley seed, absolute and herb oil. In Flavors and Fragrances: A World Perspective; Lawrence, B. M., Mookherjee, B. D., Wills, B. J., Eds.; Proceedings of the 10th International Congress of Essential Oils, Fragrances and Flavors, Washington, DC; Elsevier Science Publishers: Amsterdam, 1986; pp 715-729.
43. Shibamoto, T. Formation of sulfur- and nitrogen-containing compounds from the reaction of furfural with hydrogen sulfide and ammonia. J. Agric. Food Chem. 1977, 25, 206-208.
44. Snyder, J. M.; Frankel, E. N.; Selke, E. Capillary gas chromatographic analysis of headspace volatiles from vegetable oils. J. Am. Oil Chem. Soc. 1985, 62, 1675-1679.
45. Stoll, M.; Winter, M.; Gautschi, F.; Flament, I.; Willhalm, B. Recherches sur les arômes. Sur l'arôme de café. I. Helv. Chim Acta 1967, 50, 628-694.
46. Swoboda, P. A. T.; Peers, K. E. trans-4,5-Epoxyhept-trans-2-enal. The major volatile compound formed by the copper and α-tocopherol induced oxidation of butterfat. J. Sci. Food Agric. 1978, 29, 803-807.
47. 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.
48. Taylor, S. L.; Berg, C. M.; Shoptaugh, N. H.; Scott, V. N. Lack of mutagens in deep-fat-fried foods obtained at the retail level. Food Chem. Toxicol. 1982, 20, 209-212.
49. Taylor, S. L.; Berg, C. M.; Shoptaugh, N. H.; Traisman, E. Mutagen formation in deep-fat fried foods as a function of frying conditions. J. Am. Oil Chem. Soc. 1983, 60, 576-580.
50. Van Gastel, A.; Mathur, R.; Roy, V. V.; Rukmini, C. Ames mutagenicity tests of repeatedly heated edible oils. Food Chem. Toxicol. 1984, 22, 403-405.
51. van Straten, S., Maarse, Eds. In Volatile Compounds in Food Qualitative Data; Division for Nutrition and Food Research, TNO: Zeist, The Netherlands, 1983.
52. Whitfield, F. Volatiles from interactions of Maillard reactions and lipids. Crit. Rev. Food Sci. Nutr. 1992, 31, 1-58.
53. Wu, C.-M.; Chen, S.-Y. Volatile compounds in oils after deep frying or stir frying and subsequent storage. J. Am. Oil Chem. Soc. 1992, 69, 858-865.
54. Yamaguchi, T.; Yamashita, Y. Mutagenicity of hydroperoxides of fatty acids and some hydrocarbons. Agric. Biol. Chem. 1980, 44, 1675-1678.
55. Zheng, G.-Q.; Kenney, P. M.; Lam, L. K. T. Myristicin: a potential cancer chemopreventative agent from parsley leaf oil. J. Agric. Food Chem. 1992a, 40, 107-110.
56. Zheng, G.-Q.; Kenney, P. M.; Zhang, B.-L.; Lam, L. K. T. Inhibition of benzo[a]pyrene-induced tumorigenesis by myristicin, a volatile aroma constituent of parsley leaf oil. Carcinogenesis 1992b, 13, 1921-1923.