Journal of Industrial and Engineering Chemistry, Vol.17, No.3, 537-542, May, 2011
Synergetic and antagonistic role of natural antioxidant in the autoxidation of soybean oil
E-mail:
The antioxidant effects of ascorbic acid (vitamin C), a-tocopherol (vitamin E), 2,6-di-t-butyl-4-cresol (BHT) and 4-hydroxy-2,2,6,6-tetramethyl-piperidine-N-oxyl (abbr. N-oxyl = 4-hydroxy-TEMPO) on the autoxidation of soybean oil (SBO) were evaluated at 140 ℃ in four different concentrations (at 1.0, 0.7, 0.5, and 0.3 wt% of SBO). Ascorbic acid and a-tocopherol showed lower active oxygen concentration at the range of 0.5.0.7 wt% concentrations than that at 1.0 wt%. However, on the contrary, 2,6-di-t-butyl-4-cresol and N-oxyl showed higher effect with increasing concentration. In 1.0 wt% antioxidant concentration, the inhibiting effect showed in the following order, 2,6-di-t-butyl-4-cresol > atocopherol > N-oxyl > ascorbic acid and in lower concentration of 0.5 wt%, the order was inverted as follows: ascorbic acid > a-tocopherol > 2,6-di-t-butyl-4-cresol > N-oxyl. The inversion of the order at lower concentration could be attributed to the synergetic and antagonistic effect arousing from hydrogen bonding. The composition of oxidized triglyceride was investigated by means of LC/ESI-MS/MS spectroscopy.
Keywords:Soybean oil;Antioxidant;Ascorbic acid;α-Tocopherol;Hydrogen bonding;Synergetic/antagonistic role
- Bernardini E, Oilseeds Oils and Fats, vols. I and II, Interstampa, Rome, 1981-1983
- Saito I, Matsuura T, The Chemistry of Active Oxygen, Japan Chemical Society, 1990 (Chapter 1).
- Lee KW, Mei BX, Bo Q, Kim YW, Chung KW, Han Y, J. Ind. Eng. Chem., and therein cited., 13(4), 530 (2007)
- Abe Y, Plastic stabilizer for PVC, Nitkankogyoshimbumsha (1966)
- Lee KW, Hailan C, Yinhua J, Kim YW, Chung KW, Korean J. Chem. Eng., 25(3), 474 (2008)
- Khot SN, Lascala JJ, Can E, Morye SS, Williams GI, Palmese GR, Kusefoglu SH, Wool RP, J. Appl. Polym. Sci., 82(3), 703 (2001)
- Emanuel NM, Liquid Phase Oxidation of Hydrocarbons, Plenum Press, New York, (Chapter 6)., 223 (1967)
- Judde A, Villeneuve P, Rossignol-Castera A, Le Guillou A, J. Am. Oil Chem. Soc., 80, 1209 (2003)
- Nihro Y, Miyadaka H, Sudo T, Matsumoto H, Satoh T, J. Med. Chem., 34, 2152 (1991)
- Liu ZQ, J. Phys. Chem. A., 110, 6371 (2006)
- Weissermel K, Arpe HJ, Industrielle Organische Chemie, Verlag Chemie, pp. 199, 120.124, 292, 302.305. (1976)
- Lee IK, Yun BS, Bioorg. Med. Chem. Lett., 16, 2376 (2006)
- Katsuyama K, Inoue T, Takahashi T, Kai T, J. Jpn. Petrol. Inst., 49, 121 (2006)
- Klemchuk PP, ‘‘Antioxidant’’, Ullmann’s Encycl.Ind. Chem, vol. A3, VCH, 91 (1985)
- Lee KW, Hong Z, Piao F, Kim YW, Chung KW, J. Ind. Eng. Chem., 16(3), 419 (2010)
- Chungsan Chemical Co., CSS . J 520, October 1 (2003)
- Lee KW, Choi MJ, Kim SB, Choi CS, Ind. Eng. Chem. Res., 26, 1951 (1987)
- LG-QA-20-03-A, April 15 (2002)
- Hvattum E, Rapid Commun. Mass Spectrum., 15, 187 (2001)
- Kinen MM, Afaf Kamal-Eldin AM, Hopia LA, J. Am. Oil Chem. Soc., 77(8), 801 (2000)