Chemical analysis of polymerization products in abused fats and oils

1983

Enzymatic hydrolysis of the acylglycerol products obtained from thermally oxidized vegetable oils was studied. Corn, sunflower and soybean oils were heated in the laboratory at 180 C for 50, 70 and 100 hr with aeration and directly fractionated by silicic acid column chromatography. By successive elution with 20%, then 60% isopropyl ether in n-hexane, and diethyl ether, the thermally oxidized oils were separated into three fractions: the nonpolar fraction (monomeric compounds), slightly polar fraction (dimeric compounds), and polar fraction comprising oligomeric compounds. Enzymatic hydrolysis with pancreatic lipase showed that the monomers were hydrolyzed as rapidly as the corresponding unheated oils, the dimers much more slowly, and the oligomeric compounds barely at all. Overall, the hydrolysis of the dimers was less than 23% of that for the monomers, with small differences among the oils. Longer heating periods resulted in greater reductions in hydrolysis of the dimeric compounds. These results suggest that the degree of enzymatic hydrolysis of the fractionated acylglycerol compounds is related to differences in the thermal oxidative deterioration, and amounts of polar compounds in the products.

Section: Analyses Of Oilsmentioning

confidence: 99%

Enzymatic hydrolysis of fractionated products from oils thermally oxidized in the laboratory

1983

“…Chemical reactions such as thermal and oxidative decompositions produce both volatile and nonvolatile products, which can have adverse effects on experimental animals (8-II). Many decomposition products, both volatile (12,13) and nonvolatile (13)(14)(15)(16)(17), have been identified during the last 20 years. However, no studies had been reported on the effects of heating with aeration on the composition of triacylglycerol species.…”

Section: Introductionmentioning

confidence: 99%

Changes in the structure of soybean triacylglycerols due to heat

1984

Commercially refined soybean oil was heated at 180 C for 50, 70 or 100 hr with aeration. The triacylglycerol fractions separated from the oils by column chromatography on silica gel were fractionated further by silicic acid thin layer chromatography (TLC), and species compositions were determined by argentation TLC and lipase hydrolysis. There was a decrease in the absolute amounts of the triacylglycerols with longer heating periods, such as 21% for 50 hr and 42% for 100 hr. Relatively large changes occurred in the proportion of the molecular species of the triacylglycerols during heating; there was an increase in the more saturated species, 1-4 double bonds, and a decrease in species containing 5-7 double bonds. Although these changes occurred in the percentage of each triacylglycerol species, the positional distribution of the fatty acids in the 2-position remained virtually unchanged throughout heating. Oleic and linoleic acids were commonly found in the 2-position of the acylglycerol moiety, whereas most of the palmitic and stearic acids favored esterification in the 1- and 3-positions. The results indicate that unsaturated fatty acids located in the 2-position are protected significantly from thermal oxidative decomposition.

“…98% at 50 hr of the heating, 97% at 70 hr and 95% at I00 hr ( Table 2). The more polar products tended to be absorbed on the silica gel, and not eluted with the solvents (27) resulting in the lower recovery with longer heating. Therefore, the fractionated products, especially the monomers and dimers, were more purified than the original heated oils and relatively free of lipase inhibitors.…”

Section: Discussionmentioning

confidence: 99%

Enzymatic hydrolysis in vitro of thermally oxidized sunflower oil

1983

The hydrolysis of thermally oxidized sunflower oil by pancreatic lipase was studied in relation to chemical changes in the acylglycerols. Four classes of compounds (monomers, dimers, trimers and polymers) formed from the acylglycerols were separated from the heated oils by column chromatography on silica gel, and further verified by thin layer chromatography. Each fraction, after analyses for generaly properties, was subjected to a time course study of hydrolysis by pancreatic lipase over a 30-min period. After 70 hr of heating, the amount of hydrolysis for the acylglycerol dimers was only about half that of the monomers, and that for the trimers was, in turn, about one-third that of the monomers. The polymers were the least hydrolyzed and showed no further reaction after 5 min. The reduction in enzymatic hydrolysis of isolated fractions from the thermally oxidized oils indicates structural differences, related to formation of polar compounds and polymerization products. Adverse effects on animals from feeding these materials can be attributed partly to inhibition of hydrolysis resulting in less available energy.