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01700 Sigma-Aldrich

Acrylamide

purum, ≥98.0% (GC)

Synonym: 2-Propenamide, Acrylic acid amide

  • CAS Number 79-06-1

  • Linear Formula CH2=CHCONH2

  • Molecular Weight 71.08

  •  Beilstein Registry Number 605349

  •  EC Number 201-173-7

  •  MDL number MFCD00008032

  •  eCl@ss 39031205

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Properties

Related Categories Acrylamides, Core Bioreagents, Life Science Reagents for Protein Electrophoresis, Research Essentials
vapor density   2.45 (vs air)
vapor pressure   0.03 mmHg ( 40 °C)
grade   purum
assay   ≥98.0% (GC)
bp   125 °C/25 mmHg(lit.)
mp   81-87 °C
  82-86 °C(lit.)
solubility   water: soluble200 g/L at 20 °C
storage temp.   room temp

Description

Other Notes

Same product — same quality — now Sigma-Aldrich brand

Application

Acrylamide is used for preparing slab gel gradients for PAGE (Polyacrylamide Gel Electrophoresis).1

Biochem/physiol Actions

Acrylamide is a reactive, water soluble vinyl monomer. It causes a decrease in the number of neuritis per cell as well as reduces the rate of protein synthesis.2

Price and Availability

Suggested Laboratory Gloves


Laboratory GlovesThis substance has been tested against several types of hand protection for CE compliance. Click below to find the recommended gloves for handling this product.



Safety & Documentation

Safety Information

Symbol 
Signal word 
Danger
RIDADR 
UN 2074 6.1 / PGIII
WGK Germany 
3
RTECS 
AS3325000
Flash Point(F) 
280.4 °F
Flash Point(C) 
138 °C

Protocols & Articles

Peer-Reviewed Papers

References

Set your institution to view full text papers.

1. Polyspecificity of antistreptococcal murine monoclonal antibodies and their implications in autoimmunity. Cunningham MW and Swerlick RA J. Exp. Med. 164(4), 998-1012, (1986)

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2. Acrylamide-induced effects on general and neurospecific cellular functions during exposure and recovery. Nordin-Andersson M, Walum E, Kjellstrand P, et al. Cell Biol. Toxicol. 19(1), 43-51, (2003)

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The carcinogenicity of dietary acrylamide intake: a comparative discussion of epidemiological and experimental animal research. Hogervorst JG, Baars BJ, Schouten LJ, et al. Crit. Rev. Toxicol. 40(6), 485-512, (2010)

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Acrylamide concentration determines the direction and magnitude of helical membrane protein gel shifts. Rath A, Cunningham F, and Deber CM Proc. Natl. Acad. Sci. U. S. A. 110(39), 15668-73, (2013)

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Current issues in dietary acrylamide: formation, mitigation and risk assessment. Pedreschi F, Mariotti MS, and Granby K J. Sci. Food Agric. 94(1), 9-20, (2014)

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Switchable catalytic acrylamide hydrogels cross-linked by hemin/G-quadruplexes. Lu CH, Qi XJ, Orbach R, et al. Nano Lett. 13(3), 1298-302, (2013)

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Cis-trans amide bond rotamers in β-peptoids and peptoids: evaluation of stereoelectronic effects in backbone and side chains. Laursen JS, Engel-Andreasen J, Fristrup P, et al. J. Am. Chem. Soc. 135(7), 2835-44, (2013)

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Dietary acrylamide intake and the risk of colorectal cancer with specific mutations in KRAS and APC. Hogervorst JG, de Bruijn-Geraets D, Schouten LJ, et al. Carcinogenesis 35(5), 1032-8, (2014)

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Exposure to acrylamide and human cancer--a review and meta-analysis of epidemiologic studies. Pelucchi C, La Vecchia C, Bosetti C, et al. Ann. Oncol. 22(7), 1487-99, (2011)

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Optical imaging. Expansion microscopy. Chen F, Tillberg PW, and Boyden ES Science 347(6221), 543-8, (2015)

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Optimisation and validation of the analytical procedure for the determination of acrylamide in coffee by LC-MS/MS with SPE clean up. Gielecińska I and Mojska H Rocz. Panstw. Zakl. Hig. 64(2), 85-90, (2013)

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Industrial silica sand mining and its potential public health risks. Feyereisn WL Minn. Med. 96(5), 31-2, (2013)

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[Prohibited substances in cosmetics: prospect of the toxicity of acrylamide]. Shen M, Sun Z, Shi J, et al. Zhong Nan Da Xue Xue Bao. Yi Xue Ban 37(4), 424-30, (2012)

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Acrylamide in health and disease. Pruser KN and Flynn NE Front. Biosci. (Schol. Ed.) 3, 41-51, (2011)

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[General survey of mechanisms of acrylamide neurotoxicity]. Guo C, Li B, and Xiao J Wei Sheng Yan Jiu 39(3), 282-5, (2010)

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[Acrylamide. Its synthesis in processed food and ways of problem solution]. Bagriantseva OV, Shatrov GN, and Khotimchenko SA Vopr. Pitan. 79(1), 4-12, (2010)

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Application of the Margin of Exposure (MoE) approach to substances in food that are genotoxic and carcinogenic: EXAMPLE: acrylamide (CAS No. 79-06-1). Michael Bolger P, Leblanc JC, and Woodrow Setzer R Food Chem. Toxicol. 48 Suppl 1, S25-33, (2010)

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A review of the toxicology of acrylamide. Exon JH J. Toxicol. Environ. Health. B. Crit. Rev. 9(5), 397-412, (2006)

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Acrylamide in foods: a review of the science and future considerations. Lineback DR, Coughlin JR, and Stadler RH Annu. Rev. Food Sci. Technol. 3, 15-35, (2012)

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Molecular mechanism of acrylamide neurotoxicity: lessons learned from organic chemistry. LoPachin RM and Gavin T Environ. Health Perspect. 120(12), 1650-7, (2012)

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Axonal Protective Effects Of The Myelin-associated Glycoprotein. Nguyen, T., et al. J. Neurosci. 29, 630-7, (2009)

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Carbonic anhydrase inhibitors: benzenesulfonamides incorporating cyanoacrylamide moieties are low nanomolar/subnanomolar inhibitors of the tumor-associated isoforms IX and XII. Alafeefy AM, Isik S, Abdel-Aziz HA, et al. Bioorg. Med. Chem. 21(6), 1396-403, (2013)

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Investigations into acrylamide precursors in sterilized table olives: evidence of a peptic fraction being responsible for acrylamide formation. Casado FJ, Montaño A, Spitzner D, et al. Food Chem. 141(2), 1158-65, (2013)

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Development of a novel electrochemical sensor using pheochromocytoma cells and its assessment of acrylamide cytotoxicity. Sun X, Ji J, Jiang D, et al. Biosens. Bioelectron. 44, 122-6, (2013)

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Metal-binding hydrogel particles alleviate soil toxicity and facilitate healthy plant establishment of the native metallophyte grass Astrebla lappacea in mine waste rock and tailings. Bigot M, Guterres J, Rossato L, et al. J. Hazard. Mater. 248-249, 424-34, (2013)

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The acrylamide problem: a plant and agronomic science issue. Halford NG, Curtis TY, Muttucumaru N, et al. J. Exp. Bot. 63(8), 2841-51, (2012)

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Effects of certain polyphenols and extracts on furans and acrylamide formation in model system, and total furans during storage. Oral RA, Dogan M, and Sarioglu K Food Chem. 142, 423-9, (2014)

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Simultaneous determination of 3-monochloropropane-1,2-diol and acrylamide in food by gas chromatography-triple quadrupole mass spectrometry with coupled column separation. Xu XM, He HL, Zhu Y, et al. Anal. Chim. Acta 760, 93-9, (2013)

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New research developments on acrylamide: analytical chemistry, formation mechanism, and mitigation recipes. Zhang Y, Ren Y, and Zhang Y Chem. Rev. 109(9), 4375-97, (2009)

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The mechanism of the amidases: mutating the glutamate adjacent to the catalytic triad inactivates the enzyme due to substrate mispositioning. Weber BW, Kimani SW, Varsani A, et al. J. Biol. Chem. 288(40), 28514-23, (2013)

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Industrially applicable strategies for mitigating acrylamide, furan, and 5-hydroxymethylfurfural in food. Anese M, Manzocco L, Calligaris S, et al. J. Agric. Food Chem. 61(43), 10209-14, (2013)

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Adamantyl-group containing mixed-mode acrylamide-based continuous beds for capillary electrochromatography. Part IV: investigation of the chromatographic efficiency dependent on the retention mode. Al-Massaedh AA and Pyell U J. Chromatogr. A 1349, 80-9, (2014)

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New trends in quantification of acrylamide in food products. Oracz J, Nebesny E, and Zyżelewicz D Talanta 86, 23-34, (2011)

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Reduction of acrylamide formation by vanadium salt in potato French fries and chips. Kalita D and Jayanty SS Food Chem. 138(1), 644-9, (2013)

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Effect of frying instructions for food handlers on acrylamide concentration in French fries: an explorative study. Sanny M, Luning PA, Jinap S, et al. J. Food Prot. 76(3), 462-72, (2013)

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Toxicity of acrylamide and evaluation of its exposure in baby foods. Erkekoğlu P and Baydar T Nutr. Res. Rev. 23(2), 323-33, (2010)

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Adamantyl-group containing mixed-mode acrylamide-based continuous beds for capillary electrochromatography. Part I: study of a synthesis procedure including solubilization of N-adamantyl-acrylamide via complex formation with a water-soluble cyclodextrin. Al-Massaedh AA and Pyell U J. Chromatogr. A 1286, 183-91, (2013)

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Review of epidemiologic studies of dietary acrylamide intake and the risk of cancer. Lipworth L, Sonderman JS, Tarone RE, et al. Eur. J. Cancer Prev. 21(4), 375-86, (2012)

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Prolonged continuous in vitro human platelet production using three-dimensional scaffolds. Sullenbarger B Exp. Hematol. 37(1), 101-10, (2009)

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Critical review of dose-response options for F344 rat mammary tumors for acrylamide - additional insights based on mode of action. Maier A, Kohrman-Vincent M, Hertzberg R, et al. Food Chem. Toxicol. 50(5), 1763-75, (2012)

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Neurotoxicity of acrylamide in exposed workers. Pennisi M, Malaguarnera G, Puglisi V, et al. Int. J. Environ. Res. Public Health 10(9), 3843-54, (2013)

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Detection and analysis of protofibrils and fibrils of hemoglobin: implications for the pathogenesis and cure of heme loss related maladies. Iram A and Naeem A Arch. Biochem. Biophys. 533(1-2), 69-78, (2013)

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Stabilization of ferrochelatase via lysine residues on the carboxyl terminal extension. Wong KF and Ho J Protein Pept. Lett. 20(9), 977-81, (2013)

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Induction of sister chromatid exchange by acrylamide and glycidamide in human lymphocytes: role of polymorphisms in detoxification and DNA-repair genes in the genotoxicity of glycidamide. Pingarilho M, Oliveira NG, Martins C, et al. Mutat. Res. 752(1-2), 1-7, (2013)

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Dose dependent molecular effects of acrylamide and glycidamide in human cancer cell lines and human primary hepatocytes. Ehlers A, Lenze D, Broll H, et al. Toxicol. Lett. 217(2), 111-20, (2013)

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The effects of phytic acid on the Maillard reaction and the formation of acrylamide. Wang H, Zhou Y, Ma J, et al. Food Chem. 141(1), 18-22, (2013)

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Near-infrared spectroscopy as a potential tool with radial basis function for measurement of residual acrylamide in organic polymer. Zhu G, Zheng H, Zhang P, et al. Environ. Technol. 34(1-4), 91-9, (2013)

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Fractal colour: a new approach for evaluation of acrylamide contents in biscuits. Lu H and Zheng H Food Chem. 134(4), 2521-5, (2012)

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Discovery of indolyl acrylamide derivatives as human diacylglycerol acyltransferase-2 selective inhibitors. Lee K, Kim M, Lee B, et al. Org. Biomol. Chem. 11(5), 849-58, (2013)

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Protein targets of acrylamide adduct formation in cultured rat dopaminergic cells. Martyniuk CJ, Feswick A, Fang B, et al. Toxicol. Lett. 219(3), 279-87, (2013)

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Artificial receptors for the extraction of nucleoside metabolite 7-methylguanosine from aqueous media made by molecular imprinting. Krstulja A, De Schutter C, Favetta P, et al. J. Chromatogr. A 1365, 12-8, (2014)

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Among 10 sociodemographic and lifestyle variables, smoking is strongly associated with biomarkers of acrylamide exposure in a representative sample of the U.S. Population. Vesper HW, Sternberg MR, Frame T, et al. J. Nutr. 143(6), 995S-1000S, (2013)

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The effects of acrylamide polyelectrolytes on aquatic organisms: relating toxicity to chain architecture. Costa R, Pereira JL, Gomes J, et al. Chemosphere 112, 177-84, (2014)

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Camellia sinensis (green tea) extract attenuate acrylamide induced testicular damage in albino rats. Yassa HA, George SM, Refaiy Ael R, et al. Environ. Toxicol. 29(10), 1155-61, (2014)

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Effect of dose volume on the toxicokinetics of acrylamide and its metabolites and 2-deoxy-D-glucose. Burhan I. Ghanayem et al Drug Metab. Dispos. 37, 259-63, (2009)

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Molecular structure, vibrational spectra and quantum chemical MP2/DFT studies toward the rational design of hydroxyurea imprinted polymer. Prasad BB and Rai G Spectrochim. Acta. A. Mol. Biomol. Spectrosc. 105, 400-11, (2013)

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A new approach based on off-line coupling of high-performance liquid chromatography with gas chromatography-mass spectrometry to determine acrylamide in coffee brew. Blanch GP, Morales FJ, Moreno Fde L, et al. J. Sep. Sci. 36(2), 320-4, (2013)

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Serum homocysteine, arginine, citrulline and asymmetric dimethyl arginine levels, and histopathologic examination of the abdominal aorta in rats exposed to acrylamide. Toker A, Yerlikaya F, Yener Y, et al. Biotech. Histochem. 88(2), 103-8, (2013)

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The dietary acrylamide intake adversely affects the serum trace element status. Yerlikaya FH and Yener Y Biol. Trace Elem. Res. 152(1), 75-81, (2013)

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Acrylamide in snack foods. Das AB and Srivastav PP Toxicol. Mech. Methods 22(3), 163-9, (2012)

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Responses of acrylamide-treated rat bladders. Nurullahoglu-Atalik E, Okudan N, Belviranli M, et al. Bratisl. Lek. Listy 114(1), 7-11, (2013)

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Acrylamide-treatment and responses to phenylephrine and potassium in rat aorta. Nurullahoğlu-Atalık E, Okudan N, Belviranlı M, et al. Acta Physiol. Hung. 99(4), 420-9, (2012)

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[Toxicity of acrylamide and its metabolite - glicydamide]. Pingot D, Pyrzanowski K, Michałowicz J, et al. Med. Pr. 64(2), 259-71, (2013)

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Acrylamide alters cytoskeletal protein level in rat serum. Yu SF, Song FY, Yi C, et al. Biomed. Environ. Sci. 26(11), 926-9, (2013)

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Neuroscience. Tissue imaging method makes everything clear. Underwood E Science 340(6129), 131-2, (2013)

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Merck 14,129

Beil. 2,IV,1471

Aldrich MSDS 1, 32:C / Corp MSDS 1 (1), 58:C / FT-IR 2 (1), 1257:D / FT-IR 1 (1), 749:B / FT-NMR 1 (1), 1221:A / IR-Spectra (3), 438:D / IR-Spectra (2), 388:D / NMR-Reference 2 (1), 630:C / NMR-Reference 2 (1), 630:D / RegBook 1 (1), 877:K / Sax 6, 128 / Sigma FT-IR 1 (2), 247:A / Structure Index 1, 134:D:3 / Vapor Phase 3, 778:B

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