Acrylamide

Acrylamide
Names
Preferred IUPAC name
Prop-2-enamide[2]
Other names
Acrylamide
Acrylic amide[1]
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.001.067 Edit this at Wikidata
KEGG
UNII
  • InChI=1S/C3H5NO/c1-2-3(4)5/h2H,1H2,(H2,4,5) checkY
    Key: HRPVXLWXLXDGHG-UHFFFAOYSA-N checkY
  • InChI=1/C3H5NO/c1-2-3(4)5/h2H,1H2,(H2,4,5)
    Key: HRPVXLWXLXDGHG-UHFFFAOYAS
  • O=C(C=C)N
  • C=CC(=O)N
Properties
C3H5NO
Molar mass 71.079 g·mol−1
Appearance white crystalline solid, no odor[1]
Density 1.322 g/cm3
Melting point 84.5 °C (184.1 °F; 357.6 K)
Boiling point None (polymerization); decomposes at 175-300°C[1]
390 g/L (25 °C)[3]
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 potential occupational carcinogen[1]
GHS labelling:
GHS06: ToxicGHS08: Health hazard[4]
H301, H312, H315, H317, H319, H332, H340, H350, H361, H372[4]
P201, P280, P301+P310, P305+P351+P338, P308+P313[4]
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 2: Must be moderately heated or exposed to relatively high ambient temperature before ignition can occur. Flash point between 38 and 93 °C (100 and 200 °F). E.g. diesel fuelInstability 2: Undergoes violent chemical change at elevated temperatures and pressures, reacts violently with water, or may form explosive mixtures with water. E.g. white phosphorusSpecial hazards (white): no code
2
2
2
Flash point 138 °C (280 °F; 411 K)
424 °C (795 °F; 697 K)
Lethal dose or concentration (LD, LC):
100-200 mg/kg (mammal, oral)
107 mg/kg (mouse, oral)
150 mg/kg (rabbit, oral)
150 mg/kg (guinea pig, oral)
124 mg/kg (rat, oral)[5]
NIOSH (US health exposure limits):
PEL (Permissible)
 TWA 0.3 mg/m3 [skin][1]
REL (Recommended)
 Ca TWA 0.03 mg/m3 [skin][1]
IDLH (Immediate danger)
 60 mg/m3[1]
Safety data sheet (SDS) ICSC 0091
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

Acrylamide (or acrylic amide) is an organic compound with the chemical formula CH2=CHC(O)NH2. It is a white odorless solid, soluble in water and several organic solvents. From the chemistry perspective, acrylamide is a vinyl-substituted primary amide (CONH2). It is produced industrially mainly as a precursor to polyacrylamides, which find many uses as water-soluble thickeners and flocculation agents.[6]

Acrylamide forms in burnt areas of food, particularly starchy foods like potatoes, when cooked with high heat, above 120 °C (248 °F).[7] Despite health scares following its discovery in 2002, and its classification as a probable carcinogen, acrylamide from diet is thought unlikely to cause cancer in humans; Cancer Research UK categorized the idea that eating burnt food causes cancer as a "myth".[8][9]

Production

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Acrylamide can be prepared by the hydration of acrylonitrile, which is catalyzed enzymatically:[6]

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, CH=CHC(O)NH2·H2SO4. This salt can be converted to acrylamide with a base or to methyl acrylate with methanol.

Uses

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Proteins of the erythrocyte 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.[6]

Toxicity and carcinogenicity

[edit]
N-(D-glucos-1-yl)-L-asparagine, precursor to acrylamide in cooked food[10]

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.[11] 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.[8]

Europe

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According to the EFSA, the main toxicity risks of acrylamide are "Neurotoxicity, adverse effects on male reproduction, developmental toxicity and carcinogenicity".[9][12] 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.[9][13] Food industry workers exposed to twice the average level of acrylamide do not exhibit higher cancer rates.[9]

United States

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Acrylamide is classified as an extremely hazardous substance in the United States as defined in Section 302 of the U.S. Emergency Planning and Community Right-to-Know Act (42 U.S.C. 11002), and is subject to strict reporting requirements by facilities which produce, store, or use it in significant quantities.[14]

Acrylamide is considered a potential occupational carcinogen by U.S. government agencies and classified as a Group 2A carcinogen by the IARC.[15] 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.[5]

Opinions of health organizations

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Baking, grilling or broiling food causes significant concentrations of acrylamide. This discovery in 2002 led to international health concerns. Subsequent research has however found that it is not likely that the acrylamides in burnt or well-cooked food cause cancer in humans; Cancer Research UK categorizes the idea that burnt food causes cancer as a "myth".[9]

The American Cancer Society says that laboratory studies have shown that acrylamide is likely to be a carcinogen, but that as of 2019 evidence from epidemiological studies suggests that dietary acrylamide is unlikely to raise the risk of people developing most common types of cancer.[8]

Hazards

[edit]

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.[15]

Laboratory research has found that some phytochemicals may have the potential to be developed into drugs which could alleviate the toxicity of acrylamide.[16]

Mechanism of action

[edit]
Glycidamide 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.[17][18]

Occurrence in food

[edit]
French fries are cooked to a high temperature.

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 120 °C (248 °F). Production of acrylamide in the heating process was shown to be temperature-dependent. It was not found in food that had been boiled,[19] or in foods that were not heated.[20]

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.[21] 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.[21]

Acrylamide levels appear to rise as food is heated for longer periods of time. Although researchers are still unsure of the precise mechanisms by which acrylamide forms in foods,[22] 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 120 °C (248 °F).[23][24]

Later studies have found acrylamide in black olives,[25] dried plums,[26][27] dried pears,[26] coffee,[28][29] and peanuts.[27]

The US FDA has analyzed a variety of U.S. food products for levels of acrylamide since 2002.[30]

Occurrence in cigarettes

[edit]

Cigarette smoking is a major acrylamide source.[31][32] It has been shown in one study to cause an increase in blood acrylamide levels three-fold greater than any dietary factor.[33]

See also

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References

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  1. ^ a b c d e f g NIOSH Pocket Guide to Chemical Hazards. "#0012". National Institute for Occupational Safety and Health (NIOSH).
  2. ^ "Front Matter". Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 842. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4.
  3. ^ "Human Metabolome Database: Showing metabocard for Acrylamide (HMDB0004296)".
  4. ^ a b c Sigma-Aldrich Co., Acrylamide. Retrieved on 2022-02-15.
  5. ^ a b Centers for Disease Control and Prevention (1994). "Documentation for Immediately Dangerous To Life or Health Concentrations (IDLHs) - Acrylamide".
  6. ^ a b c Herth, Gregor; Schornick, Gunnar; l. Buchholz, Fredric (2015). "Polyacrylamides and Poly(Acrylic Acids)". Ullmann's Encyclopedia of Industrial Chemistry. pp. 1–16. doi:10.1002/14356007.a21_143.pub2. ISBN 9783527306732.
  7. ^ "Does burnt food give you cancer?". University of Birmingham. Retrieved 2022-09-30.
  8. ^ a b c "Acrylamide and Cancer Risk". American Cancer Society. 11 February 2019.
  9. ^ a b c d e "Can eating burnt foods cause cancer?". Cancer Research UK. 15 October 2021.
  10. ^ Mendel Friedman (2003). "Chemistry, Biochemistry, and Safety of Acrylamide. A Review". J. Agric. Food Chem. 51 (16): 4504–4526. doi:10.1021/jf030204+. PMID 14705871.
  11. ^ Ohara, Takashi; Sato, Takahisa; Shimizu, Noboru; Prescher, Günter; Schwind, Helmut; Weiberg, Otto; Marten, Klaus; Greim, Helmut (2003). "Acrylic Acid and Derivatives". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a01_161.pub2. ISBN 3527306730.
  12. ^ "Scientific Opinion on acrylamide in food". EFSA Journal. 13 (6). June 2015. doi:10.2903/j.efsa.2015.4104.
  13. ^ "Acrylamide and Cancer Risk". National Cancer Institute (U.S. Department of Health and Human Services). December 5, 2017. Retrieved April 23, 2018.
  14. ^ "40 C.F.R.: Appendix A to Part 355—The List of Extremely Hazardous Substances and Their Threshold Planning Quantities" (PDF). Edocket.access.gpo.gov (July 1, 2008 ed.). Government Printing Office. Archived from the original (PDF) on February 25, 2012. Retrieved October 29, 2011.
  15. ^ a b Dotson, GS (April 2011). "NIOSH skin notation (SK) profile: acrylamide [CAS No. 79-06-1]" (PDF). DHHS (NIOSH) Publication No. 2011-139.
  16. ^ Adewale OO, Brimson JM, Odunola OA, Gbadegesin MA, Owumi SE, Isidoro C, Tencomnao T (2015). "The Potential for Plant Derivatives against Acrylamide Neurotoxicity". Phytother Res (Review). 29 (7): 978–85. doi:10.1002/ptr.5353. PMID 25886076. S2CID 5465814.
  17. ^ "Scientific Opinion on acrylamide in food". EFSA Journal. 13 (6). 2015. doi:10.2903/j.efsa.2015.4104.
  18. ^ Friedman, Mendel (2003). "Chemistry, Biochemistry, and Safety of Acrylamide. A Review". Journal of Agricultural and Food Chemistry. 51 (16): 4504–4526. doi:10.1021/jf030204+. PMID 14705871.
  19. ^ "Acrylamide: your questions answered". Food Standards Agency. 3 July 2009. Archived from the original on 2012-02-12.
  20. ^ Tareke, Eden; Rydberg, Per; Karlsson, Patrik; Eriksson, Sune; Törnqvist, Margareta (August 2002). "Analysis of Acrylamide, a Carcinogen Formed in Heated Foodstuffs". Journal of Agricultural and Food Chemistry. 50 (17): 4998–5006. doi:10.1021/jf020302f. PMID 12166997.
  21. ^ a b Ono, H.; Chuda, Y.; Ohnishi-Kameyama, M.; Yada, H.; Ishizaka, M.; Kobayashi, H.; Yoshida, M. (March 2003). "Analysis of acrylamide by LC-MS/MS and GC-MS in processed Japanese foods". Food Additives and Contaminants. 20 (3): 215–220. doi:10.1080/0265203021000060887. PMID 12623644. S2CID 9380981.
  22. ^ Jung, MY; Choi, DS; Ju, JW (2003). "A Novel Technique for Limitation of Acrylamide Formation in Fried and Baked Corn Chips and in French Fries". Journal of Food Science. 68 (4): 1287–1290. doi:10.1111/j.1365-2621.2003.tb09641.x.
  23. ^ Mottram D.S.; Wedzicha B.L.; Dodson A.T. (2002). "Acrylamide is formed in the Maillard reaction". Nature. 419 (6906): 448–449. doi:10.1038/419448a. PMID 12368844. S2CID 4360610.
  24. ^ Van Noorden, Richard (5 December 2007). "Acrylamide cancer link confirmed". Chemistry World.
  25. ^ "Acrylamide detected in prune juice and olives" Food Safety & Quality Control Newsletter 26 March 2004, William Reed Business Media SAS, citing "Survey Data on Acrylamide in Food: Total Diet Study Results" Archived 2009-06-05 at the Wayback Machine United States Food and Drug Administration February 2004; later updated in June 2005, July 2006, and October 2006
  26. ^ a b Cosby, Renata (September 20, 2007). "Acrylamide in dried Fruits". ETH Life. Swiss Federal Institute of Technology Zurich. Retrieved 2017-05-29.
  27. ^ a b De Paola, Eleonora L; Montevecchi, Giuseppe; Masino, Francesca; Garbini, Davide; Barbanera, Martino; Antonelli, Andrea (February 2017). "Determination of acrylamide in dried fruits and edible seeds using QuEChERS extraction and LC separation with MS detection". Food Chemistry. 217: 191–195. doi:10.1016/j.foodchem.2016.08.101. hdl:11380/1132604. PMID 27664625.
  28. ^ Mucci, Lorelei A.; Sandin, Sven; Bälter, Katarina; Adami, Hans-Olov; Magnusson, Cecilia; Weiderpass, Elisabete (16 March 2005). "Acrylamide Intake and Breast Cancer Risk in Swedish Women". JAMA. 293 (11): 1322–1327. doi:10.1001/jama.293.11.1326. PMID 15769965. S2CID 46166341.
  29. ^ Top Eight Foods by Acrylamide Per Portion Archived 2016-03-02 at the Wayback Machine. p. 17. jifsan.umd.edu (2004). Retrieved on 2012-06-11.
  30. ^ "Survey Data on Acrylamide in Food". FDA. 20 February 2020.
  31. ^ "Public Health Statement for Acrylamide". ATSDR. CDC. December 2012.
  32. ^ Vesper, H. W.; Bernert, J. T.; Ospina, M.; Meyers, T.; Ingham, L.; Smith, A.; Myers, G. L. (1 November 2007). "Assessment of the Relation between Biomarkers for Smoking and Biomarkers for Acrylamide Exposure in Humans". Cancer Epidemiology, Biomarkers & Prevention. 16 (11): 2471–2478. doi:10.1158/1055-9965.EPI-06-1058. PMID 18006939.
  33. ^ Thonning Olesen, Pelle; Olsen, Anja; Frandsen, Henrik; Frederiksen, Kirsten; Overvad, Kim; Tjønneland, Anne (8 January 2008). "Acrylamide exposure and incidence of breast cancer among postmenopausal women in the Danish Diet, Cancer and Health Study". International Journal of Cancer. 122 (9): 2094–2100. doi:10.1002/ijc.23359. PMID 18183576. S2CID 22388855.

Further reading

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