title: Chemistry, biochemistry, and safety of acrylamide. A review.
abstract: Acrylamide (CH2=CH-CONH2), an industrially produced alpha,beta-unsaturated (conjugated) reactive molecule, is used worldwide to synthesize polyacrylamide. Polyacrylamide has found numerous applications as a soil conditioner, in wastewater treatment, in the cosmetic, paper, and textile industries, and in the laboratory as a solid support for the separation of proteins by electrophoresis. Because of the potential of exposure to acrylamide, effects of acrylamide in cells, tissues, animals, and humans have been extensively studied. Reports that acrylamide is present in foods formed during their processing under conditions that also induce the formation of Maillard browning products heightened interest in the chemistry, biochemistry, and safety of this vinyl compound. Because exposure of humans to acrylamide can come from both external sources and the diet, a need exists to develop a better understanding of its formation and distribution in food and its role in human health. To contribute to this effort, this integrated review presents data on the chemistry, analysis, metabolism, pharmacology, and toxicology of acrylamide. Specifically covered are the following aspects: nonfood and food sources; exposure from the environment and the diet; mechanism of formation in food from asparagine and glucose; asparagine-asparaginase relationships; Maillard browning-acrylamide relationships; quenching of protein fluorescence; biological alkylation of amino acids, peptides, proteins, and DNA by acrylamide and its epoxide metabolite glycidamide; risk assessment; neurotoxicity, reproductive toxicity, and carcinogenicity; protection against adverse effects; and possible approaches to reducing levels in food. Further research needs in each of these areas are suggested. Neurotoxicity appears to be the only documented effect of acrylamide in human epidemiological studies; reproductive toxicity, genotoxicity/clastogenicity, and carcinogenicity are potential human health risks on the basis of only animal studies. A better understanding of the chemistry and biology of pure acrylamide in general and its impact in a food matrix in particular can lead to the development of improved food processes to decrease the acrylamide content of the diet.
authors.affiliation: Western Regional Research Center, Agricultural Research Service, U.S. Department of Agriculture, 800 Buchanan Street, Albany, California 94710, USA. mfried@pw.usda.gov
authors.forename: Mendel
authors.initials: M
authors.lastname: Friedman
mesh_terms: D020106:Acrylamide / Q000032:analysis / Q000737:chemistry* / Q000633:toxicity*; D000180:Acrylic Resins / Q000138:chemical synthesis; D000478:Alkylation; D000818:Animals; D001216:Asparagine / Q000737:chemistry; D004781:Environmental Exposure; D005504:Food Analysis; D005511:Food Handling; D006801:Humans; D015416:Maillard Reaction; D009369:Neoplasms / Q000139:chemically induced; D009420:Nervous System / Q000187:drug effects; D012098:Reproduction / Q000187:drug effects; D012307:Risk Factors; D000099166:Polyacrylamides
chemical_list: D020106:Acrylamide; D000180:Acrylic Resins; D001216:Asparagine; D000099166:Polyacrylamides