Formation of acrylamide from lipids.
Heating amino acids with dietary oils or animal fats at elevated temperatures produced various amounts of acrylamide. The amount of acrylamide formation corresponded to the degree of unsaturation of the oils and animal fats. The decreasing order of acrylamide formation from dietary oils or animal fats with asparagine was sardine oil (642 microg/g asparagine) > cod liver oil (435.4 microg/g) > soybean oil (135.8 microg/g) > corn oil (80.7 microg/g) > olive oil (73.6 microg/g) > canola oil (70.7 microg/g) > corn oil (62.1 microg/g) > beef fat (59.3 microg/g) > lard (36.0 microg/g). Three-carbon unit compounds such as acrylic acid and acrolein, which are formed from lipids by oxidation also produced acrylamide by heat treatment with amino acids, in particular with asparagine. The results of the present study suggest that acrylamide forms in asparagine-rich foods during deep fat frying in the absence reducing sugars.
Ehling
Stefan
S
Department of Environmental Toxicology, University of California Davis, One Shield Ave, Davis, CA 95616, USA. sehling@ucdavis.edu
Hengel
Matt
M
Shibamoto
Takayuki
T
D000171:Acrolein / Q000737:chemistry; D020106:Acrylamide / Q000737:chemistry*; D000179:Acrylates / Q000737:chemistry; D000596:Amino Acids / Q000737:chemistry; D001216:Asparagine / Q000737:chemistry; D002241:Carbohydrates / Q000737:chemistry; D002849:Chromatography, Gas; D002853:Chromatography, Liquid; D003060:Cod Liver Oil / Q000737:chemistry; D003314:Corn Oil / Q000737:chemistry; D004041:Dietary Fats / Q000032:analysis; D004042:Dietary Fats, Unsaturated / Q000032:analysis; D004305:Dose-Response Relationship, Drug; D005229:Fatty Acids, Monounsaturated / Q000737:chemistry; D006358:Hot Temperature; D008055:Lipids / Q000737:chemistry*; D008956:Models, Chemical; D009821:Oils / Q000737:chemistry; D000069463:Olive Oil; D010100:Oxygen / Q000737:chemistry; D010938:Plant Oils / Q000737:chemistry; D000074262:Rapeseed Oil; D013024:Soybean Oil / Q000737:chemistry; D013229:Stearic Acids / Q000737:chemistry; D013696:Temperature; D014304:Triolein / Q000737:chemistry
D000179:Acrylates; D000596:Amino Acids; D002241:Carbohydrates; D004041:Dietary Fats; D004042:Dietary Fats, Unsaturated; D005229:Fatty Acids, Monounsaturated; D008055:Lipids; D009821:Oils; D000069463:Olive Oil; D010938:Plant Oils; D000074262:Rapeseed Oil; D013229:Stearic Acids; D014304:Triolein; D020106:Acrylamide; C031183:stearic acid; D001216:Asparagine; D000171:Acrolein; D013024:Soybean Oil; D003314:Corn Oil; D003060:Cod Liver Oil; C036658:acrylic acid; D010100:Oxygen; C029310:lard