Formation of 4-hydroxy-2-(E)-nonenal in a corn-soy oil blend: A controlled heating study using a French fried potato model

JAOCS, Journal of the American Oil Chemists' Society

Volumn 88, Issue 6, 2011, Pages 763-772

  LaFond, Sean I ^a   Jerrell, John P ^b   Cadwallader, Keith R ^b   Artz, William E ^b  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b UNIVERSITY OF ILLINOIS AT URBANA CHAMPAIGN   (United States)

Author keywords

4 hydroxy 2 (E) nonenal; Frying oil; HNE; Stable isotope dilution assay; Unsaturated hydroxy aldehydes

Indexed keywords

4-HYDROXY-2-(E)-NONENAL; FRYING OIL; HNE; STABLE ISOTOPE DILUTION ASSAY; UNSATURATED HYDROXY ALDEHYDES;

ALDEHYDES; CONCENTRATION (PROCESS); DRYING OILS; ISOTOPES;

HEATING;

GLYCINE MAX; SOLANUM TUBEROSUM; TRIFLUORO; ZEA MAYS;

EID: 79958863434     PISSN: 0003021X     EISSN: None     Source Type: Journal    
DOI: 10.1007/s11746-010-1738-z     Document Type: Article

References (32)

1. Schauenstein E, Esterbauer H, Zollner H (1977) Aldehydes in biological systems, their natural occurrence and biological activities. Pion Limited, London
2. Benedetti A, Comporti M, Esterbauer H (1980) Identification of 4-hydroxynonenal as a cytotoxic product originating from the peroxidation of liver microsomal lipids. Biochim Biophys Acta 620:281-296 (Pubitemid 11216247)
3. Guillen MD, Goicoechea E (2008) Toxic oxygenated a, β-unsaturated aldehydes and their study in foods: a review. Crit Rev Food Sci Nutr 48:119-136 (Pubitemid 351263318)
4. Nakamura T, Toyomizu M (1982) Lipid degradation products capable of reacting with amino acid. II. Identification of hydroxyl and hydroperoxyl carbonyls in autoxidized triglyceride. Nippon Suisan Gakk 48:1357-1362
5. Seppanen CM, Csallany AS (2002) Formation of 4-hydroxynonenal, a toxic aldehyde, in soybean oil at frying temperature. J Am Oil Chem Soc 79:1033-1038 (Pubitemid 35295488)
6. Grootveld M, Atherton MD, Sheerin AN, Hawkes J, Blake D, Richens TE, Silwood CJL, Lynch E, Claxson AWD (1998) In vivo absorption, metabolism, and urinary excretion of alpha, beta-unsaturated aldehydes in experimental animals. J Clin Invest 101:1210-1218
7. Indart A, Viana M, Grootveld MC, Silwood CJL, S'anchez-Vera I, Bonet B (2002) Teratogenic actions of thermally-stressed culinary oils in rats. Free Rad Res 36:1051-1058
8. Seppanen CM, Csallany AS (2001) Simultaneous determination of lipophilic aldehydes by high-performance liquid chromatography in vegetable oil. J Am Oil Chem Soc 78:1253-1260 (Pubitemid 34180241)
9. Surh J, Kwon H (2005) Estimation of daily exposure to 4-hydroxy-2-alkenals in Korean foods containing n-3 and n-6 polyunsaturated fatty acids. Food Addit Contam 22:701-708 (Pubitemid 41236602)
10. Kawai Y, Takeda S, Terao J (2007) Lipidomic analysis for lipid peroxidation-derived aldehydes using gas chromatography-mass spectrometry. Chem Res Toxicol 20:99-107 (Pubitemid 46220160)
11. Gupta MK, Warner K, White PJ (eds) (2004) Frying technology and practices. AOCS Press, IL
12. Seppanen CM, Csallany AS (2004) Incorporation of the toxic aldehyde 4-hydroxy-2-trans-nonenal into food fried in thermally oxidized soybean oil. J Am Oil Chem Soc 81:1137-1141 (Pubitemid 40163210)
13. USDA Economic Research Service. (accessed Jul. 2009) ERS/ USDA Data-Food Availability (Per Capita) Data System. http://www.ers.usda.gov/Data/ FoodConsumption/
14. Firestone D (ed) (1993) AOCS official methods and recommended practices of the American Oil Chemists' Society, 4th edn. American Oil Chemists' Society, IL
15. Caldwell JD, Cooke BS, Greer MK (2009) High performance size exclusion chromatography for determination of total polar compounds in used frying oils [abstract]. In: Proceedings of 100 annual meeting of the American Oil Chemists' Society; 2009 May 3-6; Orlando, FL. Abstract # 30515
16. Chandra A, Srivastava S (1997) A synthesis of 4-hydroxy-2-trans-nonenal and 4-(3H)4-hydroxy-2-trans-nonenal. Lipids 37:779-782
17. Lin J, Welti DH, Vera FA, Fay LB, Blank I (1999) Synthesis of deuterated volatile lipid degradation products to be used as internal standards in isotope dilution assays. 1. Aldehydes. J Agric Food Chem 47:2813-2820
18. Schuh C, Schieberle P (2006) Characterization of key aroma compounds in the beverage prepared from Darjeeling black tea: quantitative differences between tea leaves and infusion. J Agric Food Chem 54:915-924
19. Lang J, Celotto C, Esterbauer H (1985) Quantitative determination of the lipid peroxidation product 4-hydroxynonenal by high performance liquid chromatography. Anal Biochem 150:369-378 (Pubitemid 16201201)
20. Cancilla DA, Que Hee SS (1992) O-(2,3,4,5,6-Pentafluorophenyl)- methylhydroxyamine hydrochloride: a versatile reagent for the determination of carbonyl-containing compounds. J Chrom 627:1-16 (Pubitemid 23016076)
21. Samuelsson B, Hamberg M, Sweeley CC (1970) Quantitative gas chromatography of prostaglandin E1 at the nanogram level: use of deuterated carrier and multiple-ion analyzer. Anal Biochem 38:301-304
22. Gaffney TE, Hammar CG, Holmstedt B, McMahon RE (1971) Ion specific detection of internal standards labeled with stable isotopes. Anal Chem 43:307-310
23. Gay ML, White KD, Obermeyer WR, Betz JM, Musser SM (2001) Determination of ephedrine-type alkaloids in dietary supplements by LC/MS using a stable-isotope labeled internal standard. J Am Oil Chem Soc 84:761-769 (Pubitemid 33615021)
24. Schneider C, Tallman KA, Porter NA, Brash AR (2001) 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 276:20831-20838
25. Chang SS, Peterson RJ, Ho C (1978) Chemical reactions involved in the frying of foods. J Am Oil Chem Soc 55:718-727
26. Perkins EG, Van Akkeren LA (1965) Heated fats. IV. Chemical changes in fats subjected to deep fat frying processes-cottonseed oil. J Am Oil Chem Soc 42:782-786
27. Fritsch CW (1981) Measurements of frying fat determination: a brief review. J Am Oil Chem Soc 58:272-274
28. Arroyo R, Cuesta C, Garddo-Polonio C, Lopez-Varela S, Sanchez-Muniz FJ (1992) High-performance size-exclusion chromatographic studies on polar components formed in sunflower oil used for frying. J Am Oil Chem Soc 69:557-563
29. Artz WE, Soheili KC, Arjona IM (1999) Esterified propoxylated glycerol soyate, a fat substitute model compound, and soy oil after heating. J Agric Food Chem 47:3816-3821 (Pubitemid 29449511)
30. Surh J, Kwon H (2003) Simultaneous determination of 4-hydroxy-2-alkenals, lipid peroxidation toxic products. Food Addit Contam 20:325-330 (Pubitemid 36656585)
31. Han IH, Csallany AS (2008) Temperature dependence of HNE formation in vegetable oils and butter oil. J Am Oil Chem Soc 85:777-782
32. Matthaus B (2008) 4-Hydroxy-2-trans-nonenal-an oxidation product of heated edible oils [abstract]. In: Proceedings of the 99th Annual Meeting of the American Oil Chemists' Society, 2008 May 18-21; Seattle, WA. LOQ5 #4