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{{Short description|Organic chemical compound}}
{{chembox
{{Chembox
| verifiedrevid = 410958738
|Watchedfields = changed
| ImageFileL1_Ref = {{chemboximage|correct|??}}
|verifiedrevid = 477241328
| ImageFileL1 = Acrylamide-2D-skeletal.png
|ImageFileL1_Ref = {{chemboximage|correct|??}}
| ImageSize = 100px
| ImageFileR1 = Acrylamide-MW-2000-3D-balls.png
|ImageFileL1 = Acrylamide-2D-skeletal.png
|ImageSize = 100px
| ImageSizeR1 = 120px
| ImageFile2 = Acrylamide-MW-2000-3D-vdW.png
|ImageFileR1 = Acrylamide-MW-2000-3D-balls.png
|PIN = Prop-2-enamide<ref name=iupac2013>{{cite book | title = Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book) | publisher = [[Royal Society of Chemistry|The Royal Society of Chemistry]] | 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>
| ImageSize2 = 150px
|OtherNames = Acrylamide<br />Acrylic amide<ref name=NIOSH/>
| IUPACName = prop-2-enamide
|Section1={{Chembox Identifiers
| OtherNames =
|IUPHAR_ligand = 4553
| Section1 = {{Chembox Identifiers
| UNII_Ref = {{fdacite|correct|FDA}}
|UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 20R035KLCI
|UNII = 20R035KLCI
| KEGG_Ref = {{keggcite|correct|kegg}}
|KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = C01659
|KEGG = C01659
| InChI = 1/C3H5NO/c1-2-3(4)5/h2H,1H2,(H2,4,5)
|InChI = 1/C3H5NO/c1-2-3(4)5/h2H,1H2,(H2,4,5)
| InChIKey = HRPVXLWXLXDGHG-UHFFFAOYAS
|InChIKey = HRPVXLWXLXDGHG-UHFFFAOYAS
| SMILES1 = C=CC(=O)N
|SMILES1 = C=CC(=O)N
| ChEMBL_Ref = {{ebicite|correct|EBI}}
|ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 348107
|ChEMBL = 348107
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
|StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C3H5NO/c1-2-3(4)5/h2H,1H2,(H2,4,5)
|StdInChI = 1S/C3H5NO/c1-2-3(4)5/h2H,1H2,(H2,4,5)
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
|StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = HRPVXLWXLXDGHG-UHFFFAOYSA-N
|StdInChIKey = HRPVXLWXLXDGHG-UHFFFAOYSA-N
| CASNo = 79-06-1
|CASNo = 79-06-1
| CASNo_Ref = {{cascite|correct|CAS}}
|CASNo_Ref = {{cascite|correct|CAS}}
|ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 28619
|ChEBI = 28619
| SMILES = O=C(C=C)N
|SMILES = O=C(C=C)N
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID=6331
|ChemSpiderID=6331
| PubChem = 6579
|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 = [[polymerization]]
| 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 = [http://www.inchem.org/documents/icsc/icsc/eics0091.htm ICSC 0091]
| 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
'''Acrylamide''' (or [[acryl]]ic [[amide]]) is a [[chemical compound]] with the [[chemical formula]] [[Carbon|C]]<sub>3</sub>[[Hydrogen|H]]<sub>5</sub>[[Nitrogen|N]][[Oxygen|O]]. Its [[IUPAC]] name is '''prop-2-enamide'''. It is a white odourless [[crystalline]] solid, soluble in [[water (molecule)|water]], [[ethanol]], [[diethyl ether|ether]], and [[chloroform]]. Acrylamide is incompatible with acids, bases, oxidizing agents, iron, and iron salts. It decomposes non-thermally to form [[ammonia]], and thermal decomposition produces [[carbon monoxide]], [[carbon dioxide]], and oxides of [[nitrogen]].
|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 ([[polymerization]]); 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 = [http://www.inchem.org/documents/icsc/icsc/eics0091.htm ICSC 0091]
|NFPA-H=2
|NFPA-F=2
|NFPA-R=2
|FlashPtC =138
|AutoignitionPtC =424
|PEL = TWA 0.3 mg/m<sup>3</sup> [skin]<ref name=NIOSH>{{PGCH|0012}}</ref>
|REL = Ca TWA 0.03 mg/m<sup>3</sup> [skin]<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 [[acryl]]ic [[amide]]) is an [[organic compound]] with the [[chemical formula]] CH<sub>2</sub>=CHC(O)NH<sub>2</sub>. It is a white odorless solid, soluble in [[water (molecule)|water]] and several organic solvents. From the chemistry perspective, acrylamide is a vinyl-substituted [[primary amide]] (CONH<sub>2</sub>). It is produced industrially mainly as a precursor to [[polyacrylamide]]s, which find many uses as water-soluble [[thickener]]s and [[flocculation|flocculation agent]]s.<ref name=Ull/>


Acrylamide forms in burnt areas of [[food]], particularly [[starchy foods]] like [[potato]]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 [[health scare]]s 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".<ref name=acs/><ref name=cruk/>
Acrylamide is prepared on an industrial scale by the hydrolysis of [[acrylonitrile]] by [[nitrile hydratase]].


==Production==
Most acrylamide is used to synthesize [[polyacrylamide]]s, which find many uses as water-soluble [[thickener]]s. These include use in [[wastewater]] treatment, [[gel electrophoresis]] ([[SDS-PAGE]]), [[papermaking]], [[ore]] processing, and the manufacture of [[permanent press]] fabrics. Some acrylamide is used in the manufacture of [[dye]]s and the manufacture of other [[monomers]].
Acrylamide can be prepared by the hydration of [[acrylonitrile]], 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 [[sulfuric acid]] 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 [[methyl acrylate]] with methanol.
Acrylamide also occurs in many cooked starchy foods and is of concern as a possible carcinogen.<ref name=tareke/> Acrylamide was accidentally discovered in foods in April 2002 by scientists in Sweden when they found the chemical in [[starch]]y foods, such as [[potato chip]]s, [[French fried potatoes|French fries]], and bread that had been heated (production of acrylamide in the heating process was shown to be temperature-dependent).<ref name=tareke>{{cite journal|author = Tareke E, Rydberg P. ''et al.''|title = Analysis of acrylamide, a carcinogen formed in heated foodstuffs|journal = J. Agric. Food. Chem.|volume = 50|issue = 17|pages = 4998–5006|year = 2002|pmid = 12166997|doi = 10.1021/jf020302f|unused_data = DUPLICATE DATA: pmid = 12166997}}</ref> It was not found in food that had been boiled<ref name="tareke"/><ref>Food Standards Agency, Acrylamide: your questions answered [http://www.food.gov.uk/safereating/chemsafe/acrylamide_branch/acrylamide_study_faq/] Retrieved on 2008-01-01</ref> or in foods that were not heated.<ref name="tareke"/>


==Uses==
In February 2009, Health Canada announced that they were assessing whether acrylamide, which occurs naturally during the cooking of French fries, potato chips, and other processed foods, is a hazard to human health and whether any regulatory action needs to be taken. They are currently collecting information on the properties and prevalence of acrylamide in order to make their assessment.<ref>[http://www.hc-sc.gc.ca/fn-an/securit/chem-chim/food-aliment/acrylamide/index-eng.php Health Canada: Acrylamide]</ref> In December 2009, after a positive reception from the food industry, Health Canada invited comment from the public on this proposal.<ref>{{cite news| url=http://www.thestar.com/news/canada/article/741811--do-you-want-anti-cancer-drug-in-junk-food?bn=1|work=The Star|location=Toronto|title=Do you want anti-cancer drug in junk food?|date=2009-12-22|accessdate=2010-04-23}}</ref>
[[File:RBC Membrane Proteins SDS-PAGE gel.jpg|thumb|left|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.<ref name=Ull/>
The [[European Chemical Agency]] added acrylamide to the list of [[substance of very high concern|substances of very high concern]] in March 2010.<ref>[http://echa.europa.eu/chem_data/authorisation_process/candidate_list_table_en.asp Candidate List of Substances of Very High Concern for authorisation]</ref>


==Toxicity and carcinogenicity==
==Laboratory use==
[[File:N-(D-glucos-1-yl)-L-asparagine.png|thumb|none|''N''-(<small>D</small>-glucos-1-yl)-<small>L</small>-asparagine, precursor to acrylamide in cooked food<ref>{{cite journal|title=Chemistry, Biochemistry, and Safety of Acrylamide. A Review|author=Mendel Friedman|journal=J. Agric. Food Chem.|year=2003|volume=51|issue=16|pages=4504–4526|doi=10.1021/jf030204+|pmid=14705871}}</ref>]]
Polyacrylamide was first used in a laboratory setting in the early 1950s. In 1959, the groups of Davis and Ornstein<ref>[http://www.pipeline.com/~lenornst/DiscElectrophoresis.html Davis and Ornstein]</ref> and of Raymond and Weintraub<ref>[http://www.sciencemag.org/cgi/content/abstract/130/3377/711 Raymond and Weintraub]</ref> independently published on the use of [[Gel electrophoresis|polyacrylamide gel electrophoresis]] to separate charged [[molecules]].<ref name=Davis>{{cite journal|author = Reynolds S, Weintraub L.|title = Acrylamide Gel as a Supporting Medium for Zone Electrophoresis|journal = Science|volume = 130|issue = 3377|page = 711|year = 1959|pmid = 14436634|doi = 10.1126/science.130.3377.711}}</ref> The technique is widely accepted today, and remains a common [[Protocol (natural sciences)|protocol]] in [[molecular biology]] labs.


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 reaction]]s, followed by dehydrogenation produces ''N''-(<small>D</small>-glucos-1-yl)-<small>L</small>-asparagine, which upon [[pyrolysis]] generates some acrylamide.
Acrylamide has many other uses in molecular biology laboratories, including the use of [[linear polyacrylamide]] (LPA) as a [[Carrier (DNA)|carrier]], which aids in the precipitation of small amounts of [[DNA]]. Many laboratory supply companies sell LPA for this use.<ref>[http://www.biocompare.com/itemdetails.asp?itemid=349470 Linear Polyacrylamide as a commercially sold DNA carrier]</ref>


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> [[International Agency for Research on Cancer|IARC]], [[National Toxicology Program|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]].<ref name=acs/>
==Prepared foods==
Acrylamide levels appear to rise as food is heated for longer periods of time. Though researchers are still unsure of the precise mechanisms by which acrylamide forms in foods, many believe it is a byproduct of the [[Maillard reaction]]. In [[frying|fried]] or [[baking|baked]] goods, acrylamide may be produced by the reaction between [[asparagine]] and [[reducing sugar]]s ([[fructose]], [[glucose]], etc.) or reactive [[carbonyl]]s at temperatures above {{convert|120|°C|°F|abbr=on}}.<ref name=mottram>{{cite journal|author = Mottram DS, Wedzicha BL. and Dodson AT.|title = Acrylamide is formed in the Maillard reaction|journal = Nature|volume = 419|issue = 6906|pages = 448–449|year = 2002|pmid = 12368844|doi = 10.1038/419448a|unused_data = DUPLICATE DATA: pmid = 12368844}}</ref><ref>Chemistry World, Acrylamide cancer link confirmed [http://www.rsc.org/chemistryworld/News/2007/December/05120703.asp] Retrieved on 2008-01-01</ref>


===Europe===
A study by the [[U.S. Food and Drug Administration]] (FDA) proposed a mechanism that involves [[asparagine]], which, when heated in the presence of [[glucose]], forms acrylamide.
According to the [[EFSA]], the main toxicity risks of acrylamide are "[[Neurotoxicity]], adverse effects on male reproduction, [[developmental toxicity]] and [[carcinogen]]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-[[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 method|epidemiological studies]] 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=[[National Cancer Institute]] (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===
Based on current stage of knowledge, acrylamide is a natural byproduct that forms when certain carbohydrate-rich foods are fried, baked, or roasted at temperatures above 120 °C. Acrylamide causes cancer in rats when administered orally in high-dose experiments, increasing tumors in the nervous system, oral cavity, peritoneum, thyroid gland, mammary gland, uterus, and clitoris.<ref>[http://potency.berkeley.edu/chempages/ACRYLAMIDE.html Animal Test Results on Acrylamide in the Carcinogenic Potency Database]</ref> There is a margin of 900-fold between the dose that gave cancer to 10% of rats and human exposure to acrylamide in the diet.<ref>[http://potency.berkeley.edu/MOE.html Comparing Possible Cancer Hazards from Human Exposures to Rodent Carcinogens]</ref>
Acrylamide is classified as an [[List of extremely hazardous substances|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.<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=[[United States Government Publishing Office|Government Printing Office]] |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 [[List of IARC Group 2A carcinogens|Group 2A carcinogen]] by the [[International Agency for Research on Cancer|IARC]].<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 [CAS No. 79-06-1].|last = Dotson|first = GS|date = April 2011|journal = DHHS (NIOSH) Publication No. 2011-139}}</ref> The [[Occupational Safety and Health Administration]] and the [[National Institute for Occupational Safety and Health]] 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>
===Uncooked foods===
Acrylamide has been found in [[Olive#Fruit harvest and processing|black olives]],<ref>[http://www.foodqualitynews.com/Food-Alerts/Acrylamide-detected-in-prune-juice-and-olives "Acrylamide detected in prune juice and olives"] ''Food Safety & Quality Control Newsletter'' 26 March 2004, William Reed Business Media SAS, ''citing'' [http://www.fda.gov/Food/FoodSafety/FoodContaminantsAdulteration/ChemicalContaminants/Acrylamide/default.htm "Survey Data on Acrylamide in Food: Total Diet Study Results"] [[Food and Drug Administration|United States Food and Drug Administration]] February 2004; later updated in June 2005, July 2006, and October 2006</ref> prunes,<ref name="ETH">[http://www.ethlife.ethz.ch/archive_articles/070920-acrylamid/index_EN Acrylamide in dried Fruits] ETH Life (Swiss Federal Institute of Technology Zurich)</ref> and dried pears.<ref name="ETH" />


===Opinions of health organizations===
===Herbicides===
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".<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>
Acrylamide may be a natural decay product of the polyacrylamide used as a thickening agent in some commercial herbicides. Lab tests have shown that heat and light can decompose polyacrylamide into acrylamide.<ref>{{cite web|url=http://www.i-sis.org.uk/acrylamide.php|last=Cummins|first=Joe|title=Acrylamide In Cooked Foods: The Glyphosate Connection|publisher=Institute of Science in Society|date=2002-08-01|accessdate=2008-08-20}}</ref>


The [[American Cancer Society]] says that [[laboratory studies]] have shown that acrylamide is likely to be a carcinogen, but that {{as of|lc=yes|2019}} evidence from [[epidemiological]] studies suggests that [[dietary]] 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=[[American Cancer Society]]}}</ref>
===Smoking cigarettes===
[[tobacco smoking|Cigarette smoking]] is a major acrylamide source.<ref>[http://cebp.aacrjournals.org/cgi/content/abstract/16/11/2471 Assessment of the Relation between Biomarkers for Smoking and Biomarkers for Acrylamide Exposure in Humans]</ref>


===Beverages===
===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]].<ref name=NIOSHskin/>
Estimates for the proportion of acrylamide in adults’ diet coming from the consumption of [[coffee]] range from twenty to forty percent; [[plum|prune]] juice has a high concentration of acrylamide, though adults consume it in far smaller quantities.<ref>[http://jifsan.umd.edu/docs/acry2004/acry_2004_dinovihoward.pdf page 17 Top Eight Foods by Acrylamide Per Portion]</ref>


Laboratory research has found that some [[phytochemical]]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>
===Cooking methods that affect acrylamide production===
Acrylamide cannot be created by boiling, and very few uncooked foods contain any detectable amounts.


===Mechanism of action===
[[Maillard reaction|Browning]] during [[baking]], [[frying]] or [[deep-frying]] will produce acrylamide, and over-cooking foods may produce large amounts of acrylamide. The FDA has analyzed a variety of U.S. food products for levels of acrylamide since 2002. Results of the analysis can be found here.<ref>http://www.fda.gov/Food/FoodSafety/FoodContaminantsAdulteration/ChemicalContaminants/Acrylamide/ucm053549.htm</ref>
[[file:Glycidamide.svg|thumb|left|[[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]].<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==
==Reduction of acrylamide formation==
[[File:Too hot fried french fries IMG 0660.JPG|thumb|French fries are cooked to a high temperature.]]
The [[Confederation of the Food and Drink Industries]] in the EU (CIAA) has published a number of brochures to help people reduce the amount of acrylamide formed in their food. They offer a general acrylamide "toolbox"<ref>[http://www.ciaa.be/asp/documents/brochures_form.asp?doc_id=41 “toolbox”]</ref> as well as publications specific to reducing the acrylamide in biscuits, crackers & crispbreads,<ref>[http://www.caobisco.com/doc_uploads/biscuitsenfinal.pdf biscuits, crackers & crispbreads]</ref> bread products,<ref>[http://www.ciaa.be/documents/others/bread-EN-final.pdf bread products]</ref> breakfast cereals<ref>[http://www.ciaa.be/documents/others/cereals-EN-final.pdf breakfast cereals]</ref> potato crisps (chips),<ref>[http://www.ciaa.be/documents/others/crisps-EN-final.pdf potato crisps (chips)]</ref> and French fries.<ref>[http://www.ciaa.be/documents/others/french%20fries-EN-final.pdf French fries]</ref>
Acrylamide was discovered in foods, mainly in [[starch]]y foods, such as [[potato chip]]s (UK: ''potato crisps''), [[French fried potatoes|French fries]] (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 [[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.<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. [[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.<ref name=Ono03/>
===Storage===
In the case of potatoes, for instance, the storage temperature should not drop below {{convert|8|°C|°F|abbr=on}}. When the temperature is as low as {{convert|4|°C|°F|abbr=on}} the [[reducing sugar]] content rises sharply, so that the acrylamide formation during baking or deep-frying will be higher. <ref> De Wilde T, De Meulenaer B, Mestdagh F, Govaert Y, Vandeburie S, Ooghe W, Fraselle S, Demeulemeester K, Van Peteghem C, Calus A, Degroodt JM, Verhe RA. (2005) Influence of storage practices on acrylamide formation during potato frying. Journal of Agricultural and Food Chemistry 53(16), 6550-6557</ref>


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 [[Maillard reaction]]. In [[frying|fried]] or [[baking|baked]] goods, acrylamide may be produced by the reaction between [[asparagine]] and [[reducing sugar]]s ([[fructose]], [[glucose]], etc.) or reactive [[carbonyl]]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 =[[Chemistry World]]|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>
===Raw material===
New varieties of [[potato]]es that produce less or no acrylamide are being bred. Using varieties that are low in sugar such as sweet potatoes and blanching the raw potato before frying or roasting removes some of the sugars, thereby rendering the acrylamide in the end-product.<ref>Spivey, A. (2010). A matter of degrees: advancing our understanding of acrylamide. Environmental Health Perspectives, 118, 160(8). Retrieved October 20, 2010, from Health Reference Center-Academic database.</ref> Experiments have also been conducted with oregano extract, which have resulted in a reduction of up to 49% of acrylamide in potatoes.<ref>Ciesarová, Z., Kotsiou, K., Kukurová, K., Tasioula-Margari, M. (2010). Impact of oregano and virgin olive oil phenolic compoungs on acrylamide content in a model system and fresh potatoes. Food Chemistry 123(4), 1149-55. Retrieved October 22, 2010, from ScienceDirect database.</ref>


Later studies have found acrylamide in [[Olive#Harvesting|black olives]],<ref>[http://www.foodqualitynews.com/Food-Alerts/Acrylamide-detected-in-prune-juice-and-olives "Acrylamide detected in prune juice and olives"] ''Food Safety & Quality Control Newsletter'' 26 March 2004, William Reed Business Media SAS, ''citing'' [https://www.fda.gov/Food/FoodSafety/FoodContaminantsAdulteration/ChemicalContaminants/Acrylamide/default.htm "Survey Data on Acrylamide in Food: Total Diet Study Results"] {{webarchive|url=https://web.archive.org/web/20090605153328/https://www.fda.gov/Food/FoodSafety/FoodContaminantsAdulteration/ChemicalContaminants/Acrylamide/default.htm |date=2009-06-05 }} [[Food and Drug Administration|United States Food and Drug Administration]] February 2004; later updated in June 2005, July 2006, and October 2006</ref> [[dried plums]],<ref name="ETH">{{cite web | url=http://www.ethlife.ethz.ch/archive_articles/070920-acrylamid/index_EN.html | title=Acrylamide in dried Fruits | work=[[ETH Life]] | 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 [[pears]],<ref name="ETH" /> [[coffee]],<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>[http://jifsan.umd.edu/docs/acry2004/acry_2004_dinovihoward.pdf Top Eight Foods by Acrylamide Per Portion] {{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 [[peanut]]s.<ref name="DEP"/>
===Production methods===
In many cases, it is advisable to lower the maximum temperature during baking. Also, new production methods such as [[Vacuum fryer|vacuum frying]] may lower the acrylamide formation.
When [[silicone]] is used as a foam inhibitor in deep-frying [[fat]]s in the [[food industry]], the acrylamide content is doubled.


The [[US FDA]] 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>
===Recipe formulation===
[[Asparaginase]], a naturally-occurring enzyme, can be added to bread or potato mixtures to reduce formation of acrylamide during cooking.<ref>{{cite conference
|last = Kornbrust
|first = B. A.
|coauthors = Stringer, M. A., Hendriksen, H. V.
|title = Enzymatic reduction of acrylamide formation using asparaginase from Aspergillus oryzae
|booktitle = World Grains Summit: Foods and Beverages
|date = September 17–20, 2006
|location = San Francisco, California USA
|url = http://www.aaccnet.org/meetings/2006/abstracts/o-94.htm}}
</ref>


==Occurrence in cigarettes==
===Cations===
[[tobacco smoking|Cigarette smoking]] is a major acrylamide source.<ref>{{cite web|website = [[ATSDR]] |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>
Gökmen and Şenyuva (2007) showed that by dipping French fries into calcium chloride, they were able to reduce acrylamide formation by up to 95%. They reported that the treatment did not affect final product quality either. In similar manner, sodium ions were able to reduce acrylamide formation by as much as 50% in a model asparagine and fructose system.<ref> Gökmen, V., Şenyuva, H., (2007). Acrylamide formation is prevented by divalent cations during the Maillard Reaction. Food Chemistry 103, 196-203. </ref>

==Some articles on the potential health risks to humans==
===Inhaled, absorbed or ingested acrylamide===
There is evidence to suggest that exposure to large doses can cause damage to the male [[reproductive]] [[gland]]s. Direct exposure to pure acrylamide by inhalation, skin absorption, or eye contact irritates the exposed [[mucous membranes]], e.g., the [[human nose|nose]], and can also cause [[sweating]], [[urinary incontinence]], [[nausea]], [[myalgia]], [[speech disorder]]s, [[numbness]], [[paresthesia]], and weakened legs and hands. In addition, the acrylamide monomer is a potent [[neurotoxin]], causing the disassembly or rearrangement of [[intermediate filament]]s.<ref name="kuperman">{{cite journal|author = Kuperman AS.|title = Effects of acrylamide on the central nervous system of the cat|journal = J. Pharmacol. Exp. Ther.|volume = 123|issue = 3|pages = 182–192|year = 1958|pmid = 13564393}}</ref><ref>Alberts, Lewis, Johnson, Raff, Roberts, and Walter,''Molecular Biology of the Cell'', 4th Edition, Routledge, March, 2002, ISBN 0-8153-3218-1</ref> Ingested acrylamide is metabolised to a chemically reactive [[epoxide]], [[glycidamide]].<ref>Joint FAO/WHO expert committee on food additives, Sixty-fourth meeting, Rome, 8–17 February 2005, [http://www.who.int/ipcs/food/jecfa/summaries/summary_report_64_final.pdf Summary and conclusions] Retrieved on 2008-01-01</ref>

===British Journal of Cancer===
One study reanalysed a population-based Swedish case-control study encompassing cases with cancer of the large bowel, bladder, and kidney, and 538 healthy controls.<ref name="nature.com">{{cite journal|doi=10.1038/sj.bjc.6600726|title=Dietary acrylamide and cancer of the large bowel, kidney, and bladder: Absence of an association in a population-based study in Sweden|year=2003|last1=Mucci|first1=L A|last2=Dickman|first2=P W|last3=Steineck|first3=G|last4=Adami|first4=H-O|last5=Augustsson|first5=K|journal=British Journal of Cancer|volume=88|page=84|pmid=12556964|issue=1|pmc=2376776}}</ref> Researchers assessed the impact of dietary acrylamide “by linking extensive food frequency data with acrylamide levels in certain food items recorded by the Swedish National Food Administration. Unconditional logistic regression was used to estimate odds ratios, adjusting for potential confounders.” They “found consistently a lack of an excess risk, or any convincing trend, of cancer of the bowel, bladder, or kidney in high consumers of 14 different food items with a high (range 300–1200 µg/kg) or moderate (range 30–299 µg/kg) acrylamide content.” Also, “Unexpectedly, an inverse trend was found for large bowel cancer (P for trend 0.01) with a 40% reduced risk in the highest compared to lowest quartile.” The article concludes “We found reassuring evidence that dietary exposure to acrylamide in amounts typically ingested by Swedish adults in certain foods has no measurable impact on risk of three major types of cancer. It should be noted, however, that relation of risk to the acrylamide content of all foods could not be studied.”<ref name="nature.com"/>

===Cancer, epidemiology, biomarkers, and prevention===
A number of studies pertaining to acrylamide have appeared in various issues of Cancer, Epidemiology, Biomarkers & Prevention. The first study included 62,573 women, aged 55–69 years.<ref name="cebp.aacrjournals.org"/> The acrylamide intake of subcohort members and cases was assessed with a food frequency questionnaire and was based on chemical analysis of all relevant Dutch foods. Subgroup analyses were done for never-smokers to eliminate the influence of smoking, an important source of acrylamide. After 11.3 years of follow-up, the researchers observed 327, 300, and 1,835 cases of endometrial, ovarian, and breast cancer, respectively. They concluded that their subjects faced “increased risks of postmenopausal endometrial and ovarian cancer with increasing dietary acrylamide intake, in particular, among never-smokers. Risk of breast cancer was not associated with acrylamide intake.”<ref name="cebp.aacrjournals.org">{{cite journal|doi=10.1158/1055-9965.EPI-07-0581|title=A Prospective Study of Dietary Acrylamide Intake and the Risk of Endometrial, Ovarian, and Breast Cancer|pmid=18006919|year=2007|last1=Hogervorst|first1=J. G.|last2=Schouten|first2=L. J.|last3=Konings|first3=E. J.|last4=Goldbohm|first4=R. A.|last5=Van Den Brandt|first5=P. A.|journal=Cancer Epidemiology Biomarkers & Prevention|volume=16|issue=11|page=2304}}</ref>

The second study sought to evaluate how much of the acrylamide humans eat is absorbed by the body. The study consisted of six young healthy volunteers consuming a meal containing 0.94&nbsp;mg of acrylamide, and then providing urine for up to 72 hours thereafter. The study concluded that “most of the acrylamide ingested with food is absorbed in humans.”<ref name=s2>{{cite journal|doi=10.1158/1055-9965.EPI-05-0647|pmid=16492914|title=Toxicokinetics of Acrylamide in Humans after Ingestion of a Defined Dose in a Test Meal to Improve Risk Assessment for Acrylamide Carcinogenicity|first9=P|last9=Pournara|first8=D|last8=Tomalik-Scharte|first7=D|last7=Taubert|first6=A|last6=Lazar|first5=A|last5=Jetter|first4=A|last4=Weyer|first3=M|last3=Kinzig-Schippers|first2=MI|year=2006|last2=Boettcher|last1=Fuhr|first1=U.|journal=Cancer Epidemiology Biomarkers & Prevention|volume=15|issue=2|page=266}}</ref>

===Heat-generated food toxicants (HEATOX)===
The Heat-generated Food Toxicants ([http://www.slv.se/default.aspx?id=1379&epslanguage=EN-GB HEATOX]) Project was a “multidisciplinary research project involving 24 partners in 14 countries.” It ran from late 2003 to early 2007. Its objectives were to “estimate health risks that may be associated with hazardous compounds in heat-treated food [, and] find cooking/processing methods that minimise the amounts of these compounds, thereby providing safe, nutritious, and high-quality food-stuffs.”<ref name="autogenerated1">[http://www.slv.se/upload/heatox/documents/D62_final_project_leaflet_.pdf heat-Generated Food Toxicants; Identification, Characterisation and Risk Minimisation]</ref><ref>[http://www.slv.se/upload/heatox/documents/Heatox_Final%20_report.pdf HEATOX, Heat-generated food toxicants: identification, characterisation and risk minimisation]</ref> It found that "the evidence of acrylamide posing a cancer risk for humans has been strengthened,"<ref name="heatox0">[http://www.slv.se/upload/heatox/documents/Pressrelease_HEATOX_project_completed_%E2%80%93_brings_new_pieces_to_the_Acrylamide_Puzzle.pdf HEATOX project completed – brings new pieces to the Acrylamide Puzzle]</ref> and that "compared with many regulated food carcinogens, the exposure to acrylamide poses a higher estimated risk to European consumers."<ref name="autogenerated1" /> HEATOX sought also to provide consumers with advice on how to lower their intake of acrylamide, specifically pointing out that home-cooked food tends to contribute far less to overall acrylamide levels than food that was industrially prepared, and that avoiding overcooking is one of the best ways to minimize exposure at home.<ref name="autogenerated1" /> The report also recommended that national authorities highlight the following:

'''Potatoes low in sugar'''
*Low-sugar potato varieties
*Maintenance of suitable storage temperature during the supply chain
*Low sugar levels in prefabricated potato products for domestic frying.

'''Best frying temperature'''
*Frying temperature in the range {{convert|145|to|170|C|F}} for deep-frying potatoes
*Clear and accurate cooking instruction on the package of pre-fried products
*Clear and accurate instruction for fryers for domestic use.

'''Golden, not brown!'''
*French fries and roasted potatoes cooked to a golden-yellow rather than golden-brown colour
*Bread toasted to the lightest colour acceptable.

===International Journal of Cancer===
In March, 2003, the [[International Journal of Cancer]] reported on a study conducted between 1991–2000 in Italy and Switzerland that analyzed the risk of cancer of the oral cavity and pharynx, esophagus, larynx, large bowel, breast, and ovaries.<ref name="autogenerated558">{{cite journal|doi=10.1002/ijc.11118|title=Fried potatoes and human cancer|pmid=12712450|year=2003|last1=Pelucchi|first1=Claudio|last2=Franceschi|first2=Silvia|last3=Levi|first3=Fabio|last4=Trichopoulos|first4=Dimitrios|last5=Bosetti|first5=Cristina|last6=Negri|first6=Eva|last7=La Vecchia|first7=Carlo|journal=International Journal of Cancer|volume=105|issue=4|page=558}}</ref> It found “reassuring evidence for the lack of an important association between consumption of fried/baked potatoes and cancer risk.”<ref name="autogenerated558"/>

More recently, in January, 2008, one of the HEATOX members published a study, stating “So far, epidemiological studies have not shown any association between human cancer risk and dietary exposure to acrylamide. The purpose of this study was to conduct a nested case control study within a prospective cohort study on the association between breast cancer and exposure to acrylamide using biomarkers.” The study found that “[a]fter adjustment for smoking behavior... a positive association was seen between acrylamide-hemoglobin levels and estrogen receptor positive breast cancer... A weak association between glycidamide hemoglobin levels and incidence of estrogen receptor positive breast cancer was also found, this association, however, entirely disappeared when acrylamide and glycidamide hemoglobin levels were mutually adjusted.”<ref name="content.nejm.org">{{cite journal|pmid=18183576|year=2008|last1=Olesen|first1=PT|last2=Olsen|first2=A|last3=Frandsen|first3=H|last4=Frederiksen|first4=K|last5=Overvad|first5=K|last6=Tjønneland|first6=A|title=Acrylamide exposure and incidence of breast cancer among postmenopausal women in the Danish Diet, Cancer and Health Study|volume=122|issue=9|pages=2094–100|doi=10.1002/ijc.23359|journal=International journal of cancer. Journal international du cancer}}</ref>

===Journal of the American Medical Association===
A 2005 study included 43,404 Swedish women in the Women’s Lifestyle and Health Cohort. The women’s greatest single source of acrylamide was from coffee (54% of intake), fried potatoes (12% of intake), and [[crisp bread]] (9% of intake). The study concluded that “Compared with the lowest quintile of acrylamide intake, there was no significantly increased risk of breast cancer in the higher quintiles and no evidence of a linear dose response. For quintile 5 compared with quintile 1, the relative risk was 1.19 (95% confidence interval, 0.91–1.55). Furthermore, there was no association between breast cancer risk and higher intake of any specific foods including coffee, fried potatoes, and crisp bread.”<ref name="jama.ama-assn.org">{{cite journal|pmid=15769965|year=2005|last1=Mucci|first1=LA|last2=Sandin|first2=S|last3=Bälter|first3=K|last4=Adami|first4=HO|last5=Magnusson|first5=C|last6=Weiderpass|first6=E|title=Acrylamide intake and breast cancer risk in Swedish women.|volume=293|issue=11|pages=1326–7|doi=10.1001/jama.293.11.1326|journal=JAMA : the journal of the American Medical Association}}</ref>

===World Health Organization===
The [[World Health Organization]] (WHO) has set up a [[clearinghouse (GIS)|clearinghouse]] for information about acrylamide that includes a database of researchers/data providers; references for research published elsewhere; information updates about the current status of research efforts; and updates on information relevant to the health risk of acrylamide in food.<ref>[http://www.who.int/foodsafety/chem/chemicals/acrylamide/en/ Acrylamide], WHO</ref>

One question the site’s FAQ addresses is whether there can be an acceptable level of acrylamide in food. The WHO states that “Acrylamide belongs to the group of chemicals thought to have no reliably identifiable ‘threshold’ of effects, meaning that very low concentrations will also result in very low risks, but not in zero risk: Some risk is always present when the chemical is ingested. However, for these carcinogens, risk is thought to increase with increasing exposure.
Very low risks (even of cancer), such as those that are less than one in one million, are considered to be acceptable to some consumers. To others this is unacceptable. The important pre-requisite for any decision is, however, a clear picture of the nature and level of the risk, as well as the potential for lowering this level. This clear picture does not exist for acrylamide at present.” <ref>[http://www.who.int/foodsafety/publications/chem/acrylamide_faqs/en/index1.html WHO|Frequently asked questions - acrylamide in food]</ref>

===American Journal of Epidemiology===
The December 1, 2009, issue of the American Journal of Epidemiology included a study conducted at the Karolinska Institute in Stockholm concerning the relationship between dietary intake of acrylamide and breast cancer. Researchers found no statistically significant association between long-term dietary acrylamide intake and breast cancer. The study examined 61,433 Swedish women who were cancerfree and completed a food frequency questionnaire in 1987–1990 and again in 1997.<ref>{{cite journal|doi=10.1093/aje/kwn319|title=Long-term Dietary Acrylamide Intake and Breast Cancer Risk in a Prospective Cohort of Swedish Women|year=2008|last1=Larsson|first1=S. C.|last2=Akesson|first2=A.|last3=Wolk|first3=A.|journal=American Journal of Epidemiology|volume=169|page=376|pmid=19015201|issue=3}}</ref>
On February 18, 2009, the same journal Advance Access published<ref>{{cite journal|doi=10.1093/aje/kwn421|title=Dietary Acrylamide Intake and Risk of Premenopausal Breast Cancer|year=2009|last1=Wilson|first1=K. M.|last2=Mucci|first2=L. A.|last3=Cho|first3=E.|last4=Hunter|first4=D. J.|last5=Chen|first5=W. Y.|last6=Willett|first6=W. C.|journal=American Journal of Epidemiology|volume=169|page=954|pmid=19224978|issue=8|pmc=2727226 }}</ref> a study by researchers at the Harvard School of Public Health and Brigham and Women’s Hospital in Boston, MA on the relationship between dietary acrylamide intake and premenopausal breast cancer. Similar to the Swedish study, the research revealed no association between dietary acrylamide intake and breast cancer risk. The study examined 90,628 premenopausal women.

===European Journal of Cancer===
The March 2009 issue of the European Journal of Cancer published a study examining the relationship between dietary intake of acrylamide and colorectal cancer. Conducted by Swedish researchers at the Karolinska Institute, this study of 45,306 men found no evidence of a link between dietary intake of acrylamide and risk for colorectal cancer.<ref>{{cite journal|doi=10.1016/j.ejca.2008.12.001|title=Dietary acrylamide intake and risk of colorectal cancer in a prospective cohort of men|year=2009|last1=Larsson|first1=Susanna C.|last2=Åkesson|first2=Agneta|last3=Bergkvist|first3=Leif|last4=Wolk|first4=Alicja|journal=European Journal of Cancer|volume=45|page=513|pmid=19121931|issue=4}}</ref>

==Safe levels of acrylamide in relation to neuropathy==
In June 2002, the Food and Agriculture Organization of the United Nations (FAO) and the World Health Organization (WHO) issued a report about the health implications of acrylamide in food. After study, the Consultation concluded that the "no observed adverse effect level" (NOAEL) for acrylamide ''neuropathy'' is 0.5&nbsp;mg/kg body weight/day and the NOAEL for fertility changes is four times higher than for peripheral neuropathy. The study continued, “On the basis of current knowledge, controlling for peripheral neuropathy is expected to control for effects on fertility. The estimated average chronic human dietary intake is in the order of 1 μg/kg body weight/day. This provides a margin between exposure and the NOAEL of 500.”<ref>[http://www.who.int/foodsafety/publications/chem/en/acrylamide_summary.pdf FAO/WHO Consultation on the Health Implications of Acrylamide in Food; Geneva, 25-27 June 2002, Summary Report]</ref>

Hence, a woman weighing {{convert|132|lb|kg}} could safely consume 30&nbsp;mg of acrylamide daily without neuropathy; a man weighing {{convert|180|lb|kg}}, about 41&nbsp;mg; a child weighing {{convert|40|lb|kg}}, 9&nbsp;mg.<ref>for these and all other unit conversions, see [http://www.convertworld.com/en/weight/Kilogram.html this])</ref>

The WHO and FAO established that the safe limit of 0.5&nbsp;mg/kg body weight/day pertains ''only'' to neuropathy. There has not been an established safe dietary limit of acrylamide as it pertains to causing cancer, since there is limited relative data.

Referring to the chart below for the amount of acrylamide in foods, in a single day, the child can eat {{convert|13|kg|lb|abbr=on}} of French fried potatoes, the woman can drink 86&nbsp;kg (~86 L, or 23 US gal) of prune juice, and the man can eat {{convert|29|kg|lb|abbr=on}} of oven-baked potatoes, and each of them will have ingested less than 50 percent of the NOAEL of acrylamide.

{| class="wikitable"
|-
! Food
! AA concentration<br /> (μg/kg)
! Portion size<br /> (g)
! AA per portion<br /> (µg)
|-
| French fries (OB)
| 698
| 70
| 48.8
|-
| Prune juice
| 174
| 140
| 24.4
|-
| French fries (RF)
| 334
| 70
| 23.3
|-
| Postum
| 93
| 240
| 22.3
|-
| Potato chips
| 546
| 30
| 16.4
|-
| Canned black olives
| 550
| 15
| 8.2
|-
| Breakfast cereal
| 131
| 55
| 7.3
|-
| Brewed coffee
| 8.5
| 240
| 3.2
|}
(adapted from [http://web.archive.org/web/20060618173600/http://www.jifsan.umd.edu/presentations/acry2004/acry_2004_dinovihoward.pdf Table: Top Eight Foods by Acrylamide Per Portion], page 17)

==Public awareness==
On April 24, 2002, the [[Swedish National Food Administration]] announced that acrylamide can be found in baked and fried starchy [[food]]s, such as [[potato chips]], [[bread]]s, and [[cookie]]s. Concern was raised mainly because of the probable [[carcinogen]]ic effects of acrylamide. This was followed by a strong but short-lived interest from the press. On 2005-08-26, [[California]] [[attorney general]] [[Bill Lockyer]] filed a lawsuit against top makers of [[french fries]] and [[potato chips]] to warn consumers of the potential risk from consuming acrylamide.<ref>[http://ag.ca.gov/newsalerts/release.php?id=1207 Attorney General Lockyer Files Lawsuit to Require Consumer Warnings About Cancer-Causing Chemical in Potato Chips and French Fries], Office of the attorney general, State of California, Department of justice</ref> The lawsuit was settled on 2008-08-01, with the food producers agreeing to cut acrylamide levels in half.<ref>[http://www.sfgate.com/cgi-bin/article.cgi?f=/c/a/2008/08/02/BAFE1244HA.DTL Lawsuit over potato chip ingredients settled] Retrieved on 2008-08-02</ref>

In 2007, more than 100 articles were written about acrylamide, according to [[Nexis]] and [[Factiva]], including pieces in the LA Times,<ref>[http://www.latimes.com/news/science/environment/la-me-kfc25apr25,0,683258.story KFC to tell diners of chemical in potatoes - Los Angeles Times]</ref> the Boston Globe,<ref>[http://www.boston.com/yourlife/health/fitness/articles/2007/09/24/does_a_chemical_formed_in_cooking_french_fries_really_cause_cancer/ Does a chemical formed in cooking french fries really cause cancer? - The Boston Globe]</ref> the Guardian,<ref>{{cite news| url=http://lifeandhealth.guardian.co.uk/food/story/0,,2221538,00.html|work=The Guardian|location=London|title=Is cooked food dangerous?|date=2007-12-04|accessdate=2010-04-23 | first=Lucy | last=Atkins}}</ref> and the Wall Street Journal, among others. Of these articles, nearly half appeared in November and December, when people were frying potatoes for [[latkes]], and roasting pigs and turkeys.

On August 1, 2008, four food manufacturers - H.J. Heinz Co., Frito-Lay, Kettle Foods Inc., and Lance Inc. - agreed to reduce levels of acrylamide in their products (such as potato chips and French fries) over a three-year period and pay a combined $3 million in fines as a settlement with the California attorney general's office. California had sued these four companies in 2005, alleging they violated a state requirement that companies post warning labels on products with carcinogens.<ref>{{cite news| url=http://news.yahoo.com/s/ap/20080802/ap_on_bi_ge/potato_chip_lawsuit |title=Settlement will reduce carcinogens in potato chips |agency=Associated Press |accessdate=2008-08-02 |archiveurl = http://web.archive.org/web/20080821235756/http://news.yahoo.com/s/ap/20080802/ap_on_bi_ge/potato_chip_lawsuit <!-- Bot retrieved archive --> |archivedate = 2008-08-21}}</ref>


==See also==
==See also==
*[[Acrydite]]: research on this compound casts light on acrylamide
*[[Acrydite]]: research on this compound casts light on acrylamide
*[[Acrolein]]
*[[Poppers|Alkyl nitrites]]
*[[Deep-frying]]<!--hyphenated!-->
*[[Deep-frying]]<!--hyphenated!-->
*[[Deep fryer]]<!--no hyphen!-->
*[[Deep fryer]]<!--no hyphen!-->
*[[Vacuum fryer]]<!--no hyphen!-->
*[[Vacuum fryer]]<!--no hyphen!-->
*[[Substance of very high concern]]
*[[Substance of very high concern]]
*[[Heterocyclic amines]]
*[[Polycyclic aromatic hydrocarbons]]


==References==
==References==
{{reflist|2}}
{{Reflist}}


==External links==
==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}}
*[http://www.acrylamide-food.org/ Acrylamide Infonet]
*[http://www.acrylamidefacts.com/ Acrylamide Facts]
*[http://www.nytimes.com/2005/09/21/business/21chips.html California Wants to Serve a Warning With Fries]
*[http://www.cfsan.fda.gov/~dms/acryfaq.html Center for Food Safety and Nutrition (cfsan.fda.gov) FAQ]
*[http://www.crime.co.nz/c-files.asp?ID=46 Court case about a suspected acrylamide poisoning]
*[http://www.epa.gov/safewater/contaminants/dw_contamfs/acrylami.html Environmental Protection Agency] ''Acrylamide and Food''
*[http://cfpub.epa.gov/ncea/cfm/iris/recordisplay.cfm?deid=187729 EPA releases a Toxicological Review of Acrylamide (External Review Draft) for public comment - 01/2008]
*[http://www.timesonline.co.uk/article/0,,8122-1740864,00.html Girls who eat chips more likely to get breast cancer]
*[http://www.hsph.harvard.edu/press/releases/press01282003.html Harvard School of Public Health press release; baked and fried food does not increase risk of certain cancers in humans]
*[http://www.hsph.harvard.edu/press/releases/press03152005.html Harvard School of Public Health press release; no breast cancer risks from acrylamide via food]
*[[International Agency for Research on Cancer|IARC]] Monograph "[http://monographs.iarc.fr/ENG/Monographs/vol60/volume60.pdf Acrylamide.]"
*[http://www.foodrisk.org/hazard/chemical/contaminants/acrylamide/index.cfm Information about Acrylamide from www.foodrisk.org]
*{{ICSC|0091|00}}
*{{INRS|title=Acrylamide|number=119|year=1992}}
*[http://www.npi.gov.au/substances/acrylamide/index.html National Pollutant Inventory - Acrylamide]
*{{PGCH|0012}}
*[http://www3.interscience.wiley.com/cgi-bin/abstract/110559266/ABSTRACT Prospective study of dietary acrylamide and risk of colorectal cancer among women]
*[http://www.konsumentverket.se/html-sidor/livsmedelsverket/enginformationakryl.htm Report about acrylamide in food and cancer risks]
*[http://www.who.int/foodsafety/chem/chemicals/acrylamide/en/ World Health Organization]


== External links ==
[[Category:Amides]]
{{commons category|Acrylamide}}

{{Consumer food safety}}
{{Authority control}}

[[Category:Acrylamides| ]]
[[Category:Carboxamides]]
[[Category:Hazardous air pollutants]]
[[Category:Hazardous air pollutants]]
[[Category:IARC Group 2A carcinogens]]
[[Category:IARC Group 2A carcinogens]]
[[Category:Monomers]]
[[Category:Monomers]]
[[Category:Reproductive toxicants]]

[[Category:Suspected fetotoxicants]]
[[ar:أكريلاميد]]
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