Acrylamide
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Names | |||
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Preferred IUPAC name
Prop-2-enamide[2] | |||
Other names
Acrylamide
Acrylic amide[1] | |||
Identifiers | |||
3D model (
JSmol ) |
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ChEBI | |||
ChEMBL | |||
ChemSpider | |||
ECHA InfoCard
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100.001.067 | ||
IUPHAR/BPS |
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KEGG | |||
PubChem CID
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UNII | |||
CompTox Dashboard (EPA)
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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
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potential occupational carcinogen[1] | ||
GHS labelling: | |||
[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) | |||
Flash point | 138 °C (280 °F; 411 K) | ||
424 °C (795 °F; 697 K) | |||
Lethal dose or concentration (LD, LC): | |||
LD50 (median dose)
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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)
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TWA 0.3 mg/m3 [skin][1] | ||
REL (Recommended)
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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).
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Acrylamide (or
Acrylamide forms in burnt areas of
Production
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
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
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.
Europe
According to the
United States
Acrylamide is classified as an
Acrylamide is considered a potential occupational carcinogen by U.S. government agencies and classified as a
Opinions of health organizations
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
Hazards
Acrylamide is also a
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
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
Acrylamide was discovered in foods, mainly in
Acrylamide has been found in
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,
Later studies have found acrylamide in
The
Occurrence in cigarettes
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
- Acrydite: research on this compound casts light on acrylamide
- Acrolein
- Alkyl nitrites
- Deep-frying
- Deep fryer
- Vacuum fryer
- Substance of very high concern
- Heterocyclic amines
- Polycyclic aromatic hydrocarbons
References
- ^ a b c d e f g NIOSH Pocket Guide to Chemical Hazards. "#0012". National Institute for Occupational Safety and Health (NIOSH).
- ISBN 978-0-85404-182-4.
- ^ "Human Metabolome Database: Showing metabocard for Acrylamide (HMDB0004296)".
- ^ a b c Sigma-Aldrich Co., Acrylamide. Retrieved on 2022-02-15.
- ^ a b Centers for Disease Control and Prevention (1994). "Documentation for Immediately Dangerous To Life or Health Concentrations (IDLHs) - Acrylamide".
- ^ ISBN 9783527306732.
- ^ "Does burnt food give you cancer?". University of Birmingham. Retrieved 2022-09-30.
- ^ a b c "Acrylamide and Cancer Risk". American Cancer Society. 11 February 2019.
- ^ a b c d e "Can eating burnt foods cause cancer?". Cancer Research UK. 15 October 2021.
- PMID 14705871.
- ISBN 978-3527306732.
- .
- ^ "Acrylamide and Cancer Risk". National Cancer Institute (U.S. Department of Health and Human Services). December 5, 2017. Retrieved April 23, 2018.
- ^ "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.
- ^ a b Dotson, GS (April 2011). "NIOSH skin notation (SK) profile: acrylamide [CAS No. 79-06-1]" (PDF). DHHS (NIOSH) Publication No. 2011-139.
- S2CID 5465814.
- .
- PMID 14705871.
- ^ "Acrylamide: your questions answered". Food Standards Agency. 3 July 2009. Archived from the original on 2012-02-12.
- PMID 12166997.
- ^ S2CID 9380981.
- .
- S2CID 4360610.
- ^ Van Noorden, Richard (5 December 2007). "Acrylamide cancer link confirmed". Chemistry World.
- ^ "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
- ^ ETH Life. Swiss Federal Institute of Technology Zurich. Retrieved 2017-05-29.
- ^ PMID 27664625.
- S2CID 46166341.
- ^ 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.
- ^ "Survey Data on Acrylamide in Food". FDA. 20 February 2020.
- ATSDR. CDC. December 2012.
- PMID 18006939.
- S2CID 22388855.
Further reading
- Lineback, David R.; Coughlin, James R.; Stadler, Richard H. (2012-04-10). "Acrylamide in Foods: A Review of the Science and Future Considerations". Annual Review of Food Science and Technology. 3 (1): 15–35. PMID 22136129.