Acrylamide

Acrylamide can be prepared by the hydration of acrylonitrile, which is catalyzed enzymatically: :CH2=CHCN + H2O → CH2=CHC(O)NH2 This reaction also is catalyzed by sulfuric acid as well as various metal salts. Treatment of acrylonitrile with sulfuric acid gives acrylamide sulfate, . This salt can be converted to acrylamide with a base or to methyl acrylate with methanol. ==Uses==

separated by use of polyacrylamide gels (SDS-PAGE) The majority of acrylamide is used to manufacture various polymers, especially polyacrylamide. This water-soluble polymer, which has very low toxicity, is widely used as thickener and flocculating agent. These functions are valuable in the purification of drinking water, corrosion inhibition, mineral extraction, and paper making. Polyacrylamide gels are routinely used in medicine and biochemistry for purification and assays. ==Toxicity and carcinogenicity==

Acrylamide can arise in some cooked foods via a series of steps by the reaction of the amino acid asparagine and glucose. This condensation, one of the Maillard reactions, followed by dehydrogenation produces N-(D-glucos-1-yl)-L-asparagine, which upon pyrolysis generates some acrylamide. The discovery in 2002 that some cooked foods contain acrylamide attracted significant attention to its possible biological effects. IARC, NTP, and the EPA have classified it as a probable carcinogen, although epidemiological studies (as of 2019) suggest that dietary acrylamide consumption does not significantly increase people's risk of developing cancer. However, according to their research, there is no concern on non-neoplastic effects. Furthermore, while the relation between consumption of acrylamide and cancer in rats and mice has been shown, it is still unclear whether acrylamide consumption has an effect on the risk of developing cancer in humans, and existing epidemiological studies in humans are very limited and do not show any relation between acrylamide and cancer in humans. Food industry workers exposed to twice the average level of acrylamide do not exhibit higher cancer rates. Acrylamide is considered a potential occupational carcinogen by U.S. government agencies and classified as a Group 2A carcinogen by the IARC. The Occupational Safety and Health Administration and the National Institute for Occupational Safety and Health have set dermal occupational exposure limits at 0.03 mg/m3 over an eight-hour workday. Following the Safe Drinking Water and Toxic Enforcement Act, products in the state of California containing Acrylamide had been placed with a warning label explaining that the product contained the chemical and that it was known to cause cancer, birth defects, and reproductive harm. However, starting in 2019, the California Chamber of Commerce challenged the warning label believing it violated first amendment rights. In June of 2025, a Federal District Court In California ruled that the warning label was unconstitutional. The American Cancer Society says that laboratory studies have shown that acrylamide is likely to be a carcinogen, but that evidence from epidemiological studies suggests that dietary acrylamide is unlikely to raise the risk of people developing most common types of cancer. Hazards Radiolabeled acrylamide is also a skin irritant and may be a tumor initiator in the skin, potentially increasing risk for skin cancer. Symptoms of acrylamide exposure include dermatitis in the exposed area, and peripheral neuropathy. Mechanism of action is the dangerous metabolite produced from acrylamide, which in turn is produced by heating certain proteins. Acrylamide is metabolized to the genotoxic derivative glycidamide. On the other hand, acrylamide and glycidamide can be detoxified via conjugation with glutathione. ==Occurrence in food==

Acrylamide was discovered in foods, mainly in starchy foods, such as potato chips (UK: potato crisps), French fries (UK: chips), and bread that had been heated higher than . Production of acrylamide in the heating process was shown to be temperature-dependent. It was not found in food that had been boiled, or in foods that were not heated. Acrylamide has been found in roasted barley tea, called mugicha in Japanese. The barley is roasted so it is dark brown prior to being steeped in hot water. The roasting process produced 200–600 micrograms/kg of acrylamide in mugicha. This is less than the >1000 micrograms/kg found in potato crisps and other fried whole potato snack foods cited in the same study and it is unclear how much of this enters the drink to be ingested. Rice cracker and sweet potato levels were lower than in potatoes. Potatoes cooked whole were found to have significantly lower acrylamide levels than the others, suggesting a link between food preparation method and acrylamide levels. many believe it is a byproduct of the Maillard reaction. In fried or baked goods, acrylamide may be produced by the reaction between asparagine and reducing sugars (fructose, glucose, etc.) or reactive carbonyls at temperatures above . Later studies have found acrylamide in black olives, dried plums, dried pears, and peanuts. ==Occurrence in cigarettes==

Cigarette smoking is a major acrylamide source. It has been shown in one study to cause an increase in blood acrylamide levels three-fold greater than any dietary factor. ==See also==