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Revision as of 20:03, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 476073948 of page Acrylamide for the Chem/Drugbox validation project (updated: '').		Latest revision as of 05:40, 24 October 2024 edit Bon courage (talk | contribs)Extended confirmed users66,157 edits →top: clarify
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			{{Short description|Organic chemical compound}}
	{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}}
	{{chembox		{{Chembox
			|Watchedfields = changed
	| verifiedrevid = 443368280
			|verifiedrevid = 477241328
	| ImageFileL1_Ref = {{chemboximage|correct|??}}
			|ImageFileL1_Ref = {{chemboximage|correct|??}}
	| ImageFileL1 = Acrylamide-2D-skeletal.png
			|ImageFileL1 = Acrylamide-2D-skeletal.png
	| ImageSize = 100px
			|ImageSize = 100px
	| ImageFileR1 = Acrylamide-MW-2000-3D-balls.png
			|ImageFileR1 = Acrylamide-MW-2000-3D-balls.png
	| ImageSizeR1 = 120px
			|PIN = Prop-2-enamide<ref name=iupac2013>{{cite book | title = Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book) | publisher = ] | date = 2014 | location = Cambridge | page = 842 | doi = 10.1039/9781849733069-FP001 | isbn = 978-0-85404-182-4| title-link = Nomenclature of Organic Chemistry | chapter = Front Matter }}</ref>
	| ImageFile2 = Acrylamide-MW-2000-3D-vdW.png
			|OtherNames = Acrylamide<br />Acrylic amide<ref name=NIOSH/>
	| ImageSize2 = 150px
			|Section1={{Chembox Identifiers
	| IUPACName = prop-2-enamide
			|IUPHAR_ligand = 4553
	| OtherNames =
			|UNII_Ref = {{fdacite|correct|FDA}}
	| Section1 = {{Chembox Identifiers
			|UNII = 20R035KLCI
	| UNII_Ref = {{fdacite|correct|FDA}}
			|KEGG_Ref = {{keggcite|correct|kegg}}
	| UNII = 20R035KLCI
			|KEGG = C01659
	| KEGG_Ref = {{keggcite|correct|kegg}}
			|InChI = 1/C3H5NO/c1-2-3(4)5/h2H,1H2,(H2,4,5)
	| KEGG = C01659
			|InChIKey = HRPVXLWXLXDGHG-UHFFFAOYAS
	| InChI = 1/C3H5NO/c1-2-3(4)5/h2H,1H2,(H2,4,5)
			|SMILES1 = C=CC(=O)N
	| InChIKey = HRPVXLWXLXDGHG-UHFFFAOYAS
			|ChEMBL_Ref = {{ebicite|correct|EBI}}
	| SMILES1 = C=CC(=O)N
			|ChEMBL = 348107
	| ChEMBL_Ref = {{ebicite|correct|EBI}}
			|StdInChI_Ref = {{stdinchicite|correct|chemspider}}
	| ChEMBL = 348107
			|StdInChI = 1S/C3H5NO/c1-2-3(4)5/h2H,1H2,(H2,4,5)
	| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
			|StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
	| StdInChI = 1S/C3H5NO/c1-2-3(4)5/h2H,1H2,(H2,4,5)
			|StdInChIKey = HRPVXLWXLXDGHG-UHFFFAOYSA-N
	| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
			|CASNo = 79-06-1
	| StdInChIKey = HRPVXLWXLXDGHG-UHFFFAOYSA-N
			|CASNo_Ref = {{cascite|correct|CAS}}
	| CASNo = 79-06-1
	| CASNo_Ref = {{cascite|correct|CAS}}		|ChEBI_Ref = {{ebicite|correct|EBI}}
			|ChEBI = 28619
	| ChEBI_Ref = {{ebicite|correct|EBI}}
	| ChEBI = 28619		|SMILES = O=C(C=C)N
			|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
	| SMILES = O=C(C=C)N
			|ChemSpiderID=6331
	| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
			|PubChem = 6579
	| ChemSpiderID=6331
	| PubChem = 6579
	}}
	| Section2 = {{Chembox Properties
	|C=3|H=5|N=1|O=1
	| Appearance =
	| Density = 1.13 g/cm<sup>3</sup>
	| MeltingPtC = 84.5
	| BoilingPt = -
	| Boiling_notes = ]
	| Solubility = 2.04 kg/L (25 °C)
	}}
	| Section3={{Chembox Hazards
	| GHSPictograms = {{GHSp|GHS06}}{{GHSp|GHS08}}<ref name="sigma">{{SigmaLink
	| Productgroup = Fluka
	| Productcode = 01700
	| Accessdate = June 6, 2011
	}}</ref>
	| HPhrases = {{H-phrases|301|312|315|317|319|332|340|350|361|372}}<ref name="sigma" />
	| PPhrases = {{P-phrases|201|280|301+310|305+351+338|308+313}}<ref name="sigma" />
	| ExternalMSDS =
	| EUClass=Toxic ('''T''')<br/>{{Carc2}}<br/>{{Muta2}}<br/>{{Repr3}}
	| EUIndex=616-003-00-0
	| NFPA-H=3
	| NFPA-F=2
	| NFPA-R=2
	| RPhrases={{R45}}, {{R46}}, {{R20/21}},<br/>{{R25}}, {{R36/38}}, {{R43}},<br/>{{R48/23/24/25}}, {{R62}}
	| SPhrases={{S53}}, {{S45}}
	| FlashPt=138 °C
	| Autoignition=424 °C
	}}
	}}		}}
			|Section2={{Chembox Properties
			|C=3 | H=5 | N=1 | O=1
			|Appearance = white crystalline solid, no odor<ref name=NIOSH/>
			|Density = 1.322 g/cm<sup>3</sup>
			|MeltingPtC = 84.5
			|BoilingPt = None (]); decomposes at 175-300°C<ref name=NIOSH/>
			|Solubility = 390 g/L (25 °C)<ref>{{Cite web | url=https://hmdb.ca/metabolites/HMDB0004296 | title=Human Metabolome Database: Showing metabocard for Acrylamide (HMDB0004296)}}</ref>
			}}
			|Section3={{Chembox Hazards
			|GHSPictograms = {{GHS06}}{{GHS08}}<ref name="sigma">{{Sigma-Aldrich|sial|id=01700|name=Acrylamide|accessdate=2022-02-15}}</ref>
			|HPhrases = {{H-phrases|301|312|315|317|319|332|340|350|361|372}}<ref name="sigma" />
			|PPhrases = {{P-phrases|201|280|301+310|305+351+338|308+313}}<ref name="sigma" />
			|ExternalSDS =
			|NFPA-H=2
			|NFPA-F=2
			|NFPA-R=2
			|FlashPtC =138
			|AutoignitionPtC =424
			|PEL = TWA 0.3 mg/m<sup>3</sup> <ref name=NIOSH>{{PGCH|0012}}</ref>
			|REL = Ca TWA 0.03 mg/m<sup>3</sup> <ref name=NIOSH/>
			|IDLH = 60 mg/m<sup>3</sup><ref name=NIOSH/>
			|MainHazards = potential occupational carcinogen<ref name=NIOSH/>
			|LD50 = 100-200 mg/kg (mammal, oral)<br/>107 mg/kg (mouse, oral)<br/>150 mg/kg (rabbit, oral)<br/>150 mg/kg (guinea pig, oral)<br/>124 mg/kg (rat, oral)<ref name=idlh/>
			}}
			}}
			'''Acrylamide''' (or ]ic ]) is an ] with the ] CH<sub>2</sub>=CHC(O)NH<sub>2</sub>. It is a white odorless solid, soluble in ] and several organic solvents. From the chemistry perspective, acrylamide is a vinyl-substituted ] (CONH<sub>2</sub>). It is produced industrially mainly as a precursor to ]s, which find many uses as water-soluble ]s and ]s.<ref name=Ull/>
			Acrylamide forms in burnt areas of ], particularly ] like ]es, when cooked with high heat, above {{Convert|120|C}}.<ref name=":0">{{Cite web |title=Does burnt food give you cancer? |url=https://www.birmingham.ac.uk/research/perspective/does-burnt-food-give-you-cancer.aspx |access-date=2022-09-30 |website=University of Birmingham |language=en-GB}}</ref> Despite ]s following its discovery in 2002, and its classification as a probable ], acrylamide from diet is thought unlikely to cause cancer in humans; ] categorized the idea that eating burnt food causes cancer as a "myth".<ref name=acs/><ref name=cruk/>
			==Production==
			Acrylamide can be prepared by the hydration of ], which is catalyzed enzymatically:<ref name=Ull>{{cite book |doi=10.1002/14356007.a21_143.pub2 |chapter=Polyacrylamides and Poly(Acrylic Acids) |title=Ullmann's Encyclopedia of Industrial Chemistry |year=2015 |last1=Herth |first1=Gregor |last2=Schornick |first2=Gunnar |last3=l. Buchholz |first3=Fredric |pages=1–16 |isbn=9783527306732 }}</ref>
			:CH<sub>2</sub>=CHCN + H<sub>2</sub>O → CH<sub>2</sub>=CHC(O)NH<sub>2</sub>
			This reaction also is catalyzed by ] as well as various metal salts. Treatment of acrylonitrile with sulfuric acid gives acrylamide sulfate, {{chem2|CH\dCHC(O)NH2*H2SO4}}. This salt can be converted to acrylamide with a base or to ] with methanol.
			==Uses==
			] separated by use of polyacrylamide gels (])]]
			The majority of acrylamide is used to manufacture various polymers, especially ]. 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.<ref name=Ull/>
			==Toxicity and carcinogenicity==
			]
			Acrylamide can arise in some cooked foods via a series of steps by the reaction of the amino acid ] and glucose. This condensation, one of the ]s, followed by dehydrogenation produces ''N''-(<small>D</small>-glucos-1-yl)-<small>L</small>-asparagine, which upon ] generates some acrylamide.
			The discovery in 2002 that some cooked foods contain acrylamide attracted significant attention to its possible biological effects.<ref name=Ullmann>{{Ullmann|doi=10.1002/14356007.a01_161.pub2|title=Acrylic Acid and Derivatives|year=2003|last1=Ohara|first1=Takashi|last2=Sato|first2=Takahisa|last3=Shimizu|first3=Noboru|last4=Prescher|first4=Günter|last5=Schwind|first5=Helmut|last6=Weiberg|first6=Otto|last7=Marten|first7=Klaus|last8=Greim|first8=Helmut|isbn=3527306730}}</ref> ], ], and the ] have classified it as a probable carcinogen, although ] studies (as of 2019) suggest that dietary acrylamide consumption does not significantly increase people's risk of developing ].<ref name=acs/>
			===Europe===
			According to the ], the main toxicity risks of acrylamide are "], adverse effects on male reproduction, ] and ]icity".<ref name=cruk/><ref>{{cite journal |title=Scientific Opinion on acrylamide in food |journal=EFSA Journal |date=June 2015 |volume=13 |issue=6 |doi=10.2903/j.efsa.2015.4104 |doi-access=free }}</ref> However, according to their research, there is no concern on non-] 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 ] in humans are very limited and do not show any relation between acrylamide and cancer in humans.<ref name=cruk/><ref>{{cite web |title=Acrylamide and Cancer Risk |url=https://www.cancer.gov/about-cancer/causes-prevention/risk/diet/acrylamide-fact-sheet |publisher=] (U.S. Department of Health and Human Services) |date=December 5, 2017 |access-date=April 23, 2018}}</ref> Food industry workers exposed to twice the average level of acrylamide do not exhibit higher cancer rates.<ref name=cruk/>
			===United States===
			Acrylamide is classified as an ] in the United States as defined in Section 302 of the U.S. ] (42 U.S.C. 11002), and is subject to strict reporting requirements by facilities which produce, store, or use it in significant quantities.<ref name="gov-right-know">{{Cite journal |title=40 C.F.R.: Appendix A to Part 355—The List of Extremely Hazardous Substances and Their Threshold Planning Quantities |url=http://edocket.access.gpo.gov/cfr_2008/julqtr/pdf/40cfr355AppA.pdf |url-status=dead |journal=Edocket.access.gpo.gov |edition=July 1, 2008 |publisher=] |archive-url=https://web.archive.org/web/20120225051612/http://edocket.access.gpo.gov/cfr_2008/julqtr/pdf/40cfr355AppA.pdf |archive-date=February 25, 2012 |access-date=October 29, 2011}}</ref>
			Acrylamide is considered a potential occupational carcinogen by U.S. government agencies and classified as a ] by the ].<ref name=NIOSHskin>{{Cite journal|url = https://www.cdc.gov/niosh/docs/2011-139/pdfs/2011-139.pdf|title = NIOSH skin notation (SK) profile: acrylamide .|last = Dotson|first = GS|date = April 2011|journal = DHHS (NIOSH) Publication No. 2011-139}}</ref> The ] and the ] have set dermal occupational exposure limits at 0.03&nbsp;mg/m<sup>3</sup> over an eight-hour workday.<ref name=idlh>{{cite web|author=Centers for Disease Control and Prevention|title=Documentation for Immediately Dangerous To Life or Health Concentrations (IDLHs) - Acrylamide|url=https://www.cdc.gov/niosh/idlh/79061.html|year=1994}}</ref>
			===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; ] categorizes the idea that burnt food causes cancer as a "myth".<ref name=cruk>{{cite web |url=https://www.cancerresearchuk.org/about-cancer/causes-of-cancer/cancer-myths/can-eating-burnt-foods-cause-cancer |publisher=Cancer Research UK |title=Can eating burnt foods cause cancer? |date=15 October 2021 }}</ref>
			The ] says that ] have shown that acrylamide is likely to be a carcinogen, but that {{as of|lc=yes|2019}} evidence from ] studies suggests that ] acrylamide is unlikely to raise the risk of people developing most common types of cancer.<ref name="acs">{{cite web |date=11 February 2019 |title=Acrylamide and Cancer Risk |url=https://www.cancer.org/cancer/risk-prevention/chemicals/acrylamide.html |publisher=]}}</ref>
			===Hazards===
			Radiolabeled acrylamide is also a ] and may be a ] in the skin, potentially increasing risk for skin cancer. Symptoms of acrylamide exposure include ] in the exposed area, and ].<ref name=NIOSHskin/>
			Laboratory research has found that some ]s may have the potential to be developed into drugs which could alleviate the toxicity of acrylamide.<ref>{{cite journal |vauthors=Adewale OO, Brimson JM, Odunola OA, Gbadegesin MA, Owumi SE, Isidoro C, Tencomnao T |title=The Potential for Plant Derivatives against Acrylamide Neurotoxicity |journal=Phytother Res |volume= 29|issue= 7|pages= 978–85|year=2015 |pmid=25886076 |doi=10.1002/ptr.5353 |s2cid=5465814 |type=Review}}</ref>
			===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 ]. On the other hand, acrylamide and glycidamide can be detoxified via conjugation with ].<ref>{{cite journal |doi=10.2903/j.efsa.2015.4104|title=Scientific Opinion on acrylamide in food|journal=EFSA Journal|year=2015|volume=13|issue=6|doi-access=free}}</ref><ref>{{cite journal |doi=10.1021/jf030204+|year=2003|volume=51|issue=16|last1=Friedman|first1=Mendel|title=Chemistry, Biochemistry, and Safety of Acrylamide. A Review|journal=Journal of Agricultural and Food Chemistry|pages=4504–4526|pmid=14705871}}</ref>
			==Occurrence in food==
			]
			Acrylamide was discovered in foods, mainly in ]y foods, such as ]s (UK: ''potato crisps''), ] (UK: ''chips''), and bread that had been heated higher than {{convert|120|C|F}}. Production of acrylamide in the heating process was shown to be temperature-dependent. It was not found in food that had been boiled,<ref>{{cite web|website =Food Standards Agency|title = Acrylamide: your questions answered|date = 3 July 2009 |url=http://www.food.gov.uk/safereating/chemsafe/acrylamide_branch/acrylamide_study_faq/ |url-status=dead |archive-url=https://web.archive.org/web/20120212183149/http://www.food.gov.uk/safereating/chemsafe/acrylamide_branch/acrylamide_study_faq/ |archive-date=2012-02-12 }}</ref> or in foods that were not heated.<ref name=tareke>{{cite journal |last1=Tareke |first1=Eden |last2=Rydberg |first2=Per |last3=Karlsson |first3=Patrik |last4=Eriksson |first4=Sune |last5=Törnqvist |first5=Margareta |title=Analysis of Acrylamide, a Carcinogen Formed in Heated Foodstuffs |journal=Journal of Agricultural and Food Chemistry |date=August 2002 |volume=50 |issue=17 |pages=4998–5006 |doi=10.1021/jf020302f |pmid=12166997 }}</ref>
			Acrylamide has been found in ], called ''mugicha'' in Japanese. The ] 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.<ref name=Ono03>{{cite journal |last1=Ono |first1=H. |last2=Chuda |first2=Y. |last3=Ohnishi-Kameyama |first3=M. |last4=Yada |first4=H. |last5=Ishizaka |first5=M. |last6=Kobayashi |first6=H. |last7=Yoshida |first7=M. |title=Analysis of acrylamide by LC-MS/MS and GC-MS in processed Japanese foods |journal=Food Additives and Contaminants |date=March 2003 |volume=20 |issue=3 |pages=215–220 |doi=10.1080/0265203021000060887 |pmid=12623644 |s2cid=9380981 }}</ref> 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. ] and ] 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.<ref name=Ono03/>
			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,<ref>{{Cite journal | doi=10.1111/j.1365-2621.2003.tb09641.x|title = A Novel Technique for Limitation of Acrylamide Formation in Fried and Baked Corn Chips and in French Fries| journal=Journal of Food Science| volume=68| issue=4| pages=1287–1290|year = 2003|last1 = Jung|first1 = MY| last2=Choi| first2=DS| last3=Ju| first3=JW}}</ref> many believe it is a byproduct of the ]. In ] or ] goods, acrylamide may be produced by the reaction between ] and ]s (], ], etc.) or reactive ]s at temperatures above {{convert|120|°C|°F|abbr=on}}.<ref name=mottram>{{cite journal|author1=Mottram D.S. |author2=Wedzicha B.L. |author3=Dodson A.T. |title = Acrylamide is formed in the Maillard reaction|journal = Nature|volume = 419|issue = 6906|pages = 448–449|year = 2002|doi = 10.1038/419448a| pmid = 12368844|s2cid=4360610 }}</ref><ref>{{cite web|work =]|title= Acrylamide cancer link confirmed|url = http://www.rsc.org/chemistryworld/News/2007/December/05120703.asp|last = Van Noorden|first = Richard|date = 5 December 2007}}</ref>
			Later studies have found acrylamide in ],<ref> ''Food Safety & Quality Control Newsletter'' 26 March 2004, William Reed Business Media SAS, ''citing'' {{webarchive|url=https://web.archive.org/web/20090605153328/https://www.fda.gov/Food/FoodSafety/FoodContaminantsAdulteration/ChemicalContaminants/Acrylamide/default.htm |date=2009-06-05 }} ] February 2004; later updated in June 2005, July 2006, and October 2006</ref> ],<ref name="ETH">{{cite web | url=http://www.ethlife.ethz.ch/archive_articles/070920-acrylamid/index_EN.html | title=Acrylamide in dried Fruits | work=] | publisher=Swiss Federal Institute of Technology Zurich| date=September 20, 2007 | access-date=2017-05-29| author=Cosby, Renata}}</ref><ref name="DEP">{{cite journal|last1=De Paola|first1=Eleonora L|first2=Giuseppe |last2=Montevecchi |first3=Francesca |last3=Masino |first4=Davide |last4=Garbini |first5=Martino |last5=Barbanera |first6=Andrea |last6=Antonelli |date=February 2017|title=Determination of acrylamide in dried fruits and edible seeds using QuEChERS extraction and LC separation with MS detection|journal=Food Chemistry|volume=217|pages=191–195|pmid=27664625|doi=10.1016/j.foodchem.2016.08.101|hdl=11380/1132604 |hdl-access=free }}</ref> dried ],<ref name="ETH" /> ],<ref>{{cite journal |last1=Mucci |first1=Lorelei A. |last2=Sandin |first2=Sven |last3=Bälter |first3=Katarina |last4=Adami |first4=Hans-Olov |last5=Magnusson |first5=Cecilia |last6=Weiderpass |first6=Elisabete |title=Acrylamide Intake and Breast Cancer Risk in Swedish Women |journal=JAMA |date=16 March 2005 |volume=293 |issue=11 |pages=1322–1327 |doi=10.1001/jama.293.11.1326 |pmid=15769965 |s2cid=46166341 }}</ref><ref> {{Webarchive|url=https://web.archive.org/web/20160302203549/http://jifsan.umd.edu/docs/acry2004/acry_2004_dinovihoward.pdf |date=2016-03-02 }}. p. 17. jifsan.umd.edu (2004). Retrieved on 2012-06-11.</ref> and ]s.<ref name="DEP"/>
			The ] has analyzed a variety of U.S. food products for levels of acrylamide since 2002.<ref>{{cite web |title=Survey Data on Acrylamide in Food |url=https://www.fda.gov/food/chemical-contaminants-food/survey-data-acrylamide-food |website=FDA |date=20 February 2020 }}</ref>
			==Occurrence in cigarettes==
			] is a major acrylamide source.<ref>{{cite web|website = ] |url = https://www.atsdr.cdc.gov/phs/phs.asp?id=1113&tid=236 |title = Public Health Statement for Acrylamide |date = December 2012|publisher = CDC}}</ref><ref>{{cite journal |last1=Vesper |first1=H. W. |last2=Bernert |first2=J. T. |last3=Ospina |first3=M. |last4=Meyers |first4=T. |last5=Ingham |first5=L. |last6=Smith |first6=A. |last7=Myers |first7=G. L. |title=Assessment of the Relation between Biomarkers for Smoking and Biomarkers for Acrylamide Exposure in Humans |journal=Cancer Epidemiology, Biomarkers & Prevention |date=1 November 2007 |volume=16 |issue=11 |pages=2471–2478 |doi=10.1158/1055-9965.EPI-06-1058 |pmid=18006939 |doi-access=free}}</ref> It has been shown in one study to cause an increase in blood acrylamide levels three-fold greater than any dietary factor.<ref>{{cite journal |last1=Thonning Olesen |first1=Pelle |last2=Olsen |first2=Anja |last3=Frandsen |first3=Henrik |last4=Frederiksen |first4=Kirsten |last5=Overvad |first5=Kim |last6=Tjønneland |first6=Anne |title=Acrylamide exposure and incidence of breast cancer among postmenopausal women in the Danish Diet, Cancer and Health Study |journal=International Journal of Cancer |date=8 January 2008 |volume=122 |issue=9 |pages=2094–2100 |doi=10.1002/ijc.23359 |pmid=18183576 |s2cid=22388855 |doi-access=free }}</ref>
			==See also==
			*]: research on this compound casts light on acrylamide
			*]
			*]
			*]<!--hyphenated!-->
			*]<!--no hyphen!-->
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			*]
			*]
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			==References==
			{{Reflist}}
			==Further reading==
			*{{Cite journal |last1=Lineback |first1=David R. |last2=Coughlin |first2=James R. |last3=Stadler |first3=Richard H. |date=2012-04-10 |title=Acrylamide in Foods: A Review of the Science and Future Considerations |url=https://www.annualreviews.org/doi/10.1146/annurev-food-022811-101114 |journal=Annual Review of Food Science and Technology |language=en |volume=3 |issue=1 |pages=15–35 |doi=10.1146/annurev-food-022811-101114 |pmid=22136129 |issn=1941-1413}}
			== External links ==
			{{commons category|Acrylamide}}
			{{Consumer food safety}}
			{{Authority control}}
			]
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			]