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128635 Aldrich

2-Hydroxyethyl methacrylate

contains ≤250 ppm monomethyl ether hydroquinone as inhibitor, 97%

Synonym: 1,2-Ethanediol mono(2-methylpropenoate), Glycol methacrylate, HEMA

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Properties

Related Categories Acrylic Monomers, Building Blocks, C6 to C7, Carbonyl Compounds, Chemical Synthesis,
vapor density   5 (vs air)
vapor pressure   0.01 mmHg ( 25 °C)
assay   97%
contains   ≤250 ppm monomethyl ether hydroquinone as inhibitor
refractive index   n20/D 1.453(lit.)
bp   67 °C/3.5 mmHg(lit.)
density   1.073 g/mL at 25 °C(lit.)
storage temp.   2-8°C

Description

Packaging

1 kg in poly bottle

18 kg in comp drum

500 g in poly bottle

Application

HEMA is used in the synthesis of biologically functional poly (2-hydroxyethyl methacrylate) (PHEMA) coplymers.1 It is also used to prepare light responsive membranes of PHEMA,2 HEMA/ acrylamide based specific drug release hydrogel,3 and water soluble HEMA/methacrylic acid hydrogel for drug delivery.4 Effects of HEMA on the migration of dental pulp stem cells (in vitro) may be studied.5

General description

2-Hydroxyethyl methacrylate (HEMA) was the first monomer to be used to synthesize hydrogels for biomedical applications.The water swelling properties of HEMA are enhanced by copolymerization with more hydrophilic monomers.3HEMA finds wide applications for drug delivery.

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Safety & Documentation

Safety Information

Symbol 
GHS07  GHS07
Signal word 
Warning
Hazard statements 
Precautionary statements 
Hazard Codes (Europe) 
Xi
Risk Statements (Europe) 
Safety Statements (Europe) 
26-28
WGK Germany 
1
Flash Point(F) 
204.8 °F
Flash Point(C) 
96 °C

Protocols & Articles

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Peer-Reviewed Papers

References

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1. Characterization of Pore Structure in Biologically Functional Poly (2-Hydroxyethyl Methacrylate)-Poly (Ethylene Glycol) Diacrylate (PHEMA-PEGDA) Zellander A, et al. PLoS ONE 9(5), e96709, (2014)

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2. Preparation of Light-responsive Membranes by a Combined Surface Grafting and Postmodification Process. Schöller K, et al. J. Vis. Exp. 85, e51680-e51680, (2014)

3. Influence of the ionic character of a drug on its release rate from hydrogels based on 2-hydroxyethylmethacrylate and acrylamide synthesized by photopolymerization Gomez ML, et al. Express Polymer Lett. 6(30, 189-197, (2012)

4. Water-soluble drug partitioning and adsorption in HEMA/MAA hydrogels Dursch TJ, et al. Biomaterials 35(2), 620-629, (2014)

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5. 2-Hydroxyethyl Methacrylate Inhibits Migration of Dental Pulp Stem Cells, Journal of Endodontics Drake WW, et al. J. Endod. 39(9), 1156-1160, (2013)

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Cariogenic bacteria degrade dental resin composites and adhesives. Bourbia M, Ma D, Cvitkovitch DG, et al. J. Dent. Res. 92(11), 989-94, (2013)

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Synthesis of surfactant free PCL-PEG brushed nanoparticles with tunable degradation kinetics. Ferrari R, Colombo C, Casali C, et al. Int. J. Pharm. 453(2), 551-9, (2013)

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HEMA inhibits interfacial nano-layering of the functional monomer MDP. Yoshida Y, Yoshihara K, Hayakawa S, et al. J. Dent. Res. 91(11), 1060-5, (2012)

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Construction of monomer-free, highly crosslinked, water-compatible polymers. Dailing EA, Lewis SH, Barros MD, et al. J. Dent. Res. 93(12), 1326-31, (2014)

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Polymer nanocarriers for dentin adhesion. Osorio R, Osorio E, Medina-Castillo AL, et al. J. Dent. Res. 93(12), 1258-63, (2014)

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Degree of conversion of polymer-matrix composite assessed by FTIR analysis. Tonetto MR, Pinto SC, Rastelli Ade N, et al. J. Contemp. Dent. Pract. 14(1), 76-9, (2013)

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Bond strength of resin-modified glass ionomer restorative materials using a no-rinse conditioner. Suihkonen RW, Vandewalle KS, and Dossett JM Gen. Dent. 60(6), e413-7, (2012)

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Formation and antifouling properties of amphiphilic coatings on polypropylene fibers. Goli KK, Rojas OJ, and Genzer J Biomacromolecules 13(11), 3769-79, (2012)

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Remineralization of demineralized enamel via calcium phosphate nanocomposite. Weir MD, Chow LC, and Xu HH J. Dent. Res. 91(10), 979-84, (2012)

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Dental monomers inhibit LPS-induced cytokine release from the macrophage cell line RAW264.7. Bølling AK, Samuelsen JT, Morisbak E, et al. Toxicol. Lett. 216(2-3), 130-8, (2013)

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Deterministic order in surface micro-topologies through sequential wrinkling. Yin J, Yagüe JL, Eggenspieler D, et al. Adv. Mater. 24(40), 5441-6, (2012)

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Synergistic effects of SDF-1α chemokine and hyaluronic acid release from degradable hydrogels on directing bone marrow derived cell homing to the myocardium. Purcell BP, Elser JA, Mu A, et al. Biomaterials 33(31), 7849-57, (2012)

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Non-fouling hydrogels of 2-hydroxyethyl methacrylate and zwitterionic carboxybetaine (meth)acrylamides. Kostina NY, Rodriguez-Emmenegger C, Houska M, et al. Biomacromolecules 13(12), 4164-70, (2012)

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Experimental resin cements containing bioactive fillers reduce matrix metalloproteinase-mediated dentin collagen degradation. Osorio R, Yamauti M, Sauro S, et al. J. Endod. 38(9), 1227-32, (2012)

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Effect of different adhesion strategies on bond strength of resin composite to composite-dentin complex. Özcan M and Pekkan G Oper. Dent. 38(1), 63-72, (2013)

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Aggregate formation and radiolytic degradation of amphiphilic DNA block copolymer possessing disulfide bond. Tanabe K, Asada T, and Nishimoto S Bioorg. Med. Chem. Lett. 22(23), 7045-7, (2012)

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Acoustic emission analysis of tooth-composite interfacial debonding. Cho NY, Ferracane JL, and Lee IB J. Dent. Res. 92(1), 76-81, (2013)

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Bonding of simplified adhesive systems to caries-affected dentin of primary teeth. Alves FB, Lenzi TL, Reis A, et al. J. Adhes. Dent. 15(5), 439-45, (2013)

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The photocrosslinkable tissue adhesive based on copolymeric dextran/HEMA. Wang T, Mu X, Li H, et al. Carbohydr. Polym. 92(2), 1423-31, (2013)

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Evaluation of polypropylene and poly (butylmethacrylate-co-hydroxyethylmethacrylate) nonwoven material as oil absorbent. Zhao J, Xiao C, and Xu N Environ. Sci. Pollut. Res. Int. 20(6), 4137-45, (2013)

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Extended delivery of an anionic drug by contact lens loaded with a cationic surfactant. Bengani LC and Chauhan A Biomaterials 34(11), 2814-21, (2013)

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Novel semi-interpenetrating hydrogel networks with enhanced mechanical properties and thermoresponsive engineered drug delivery, designed as bioactive endotracheal tube biomaterials. Jones DS, Andrews GP, Caldwell DL, et al. Eur. J. Pharm. Biopharm. 82(3), 563-71, (2012)

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Bond strength of adhesive systems to mineral trioxide aggregate with different time intervals. Atabek D, Sillelioğlu H, and Olmez A J. Endod. 38(9), 1288-92, (2012)

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Human gingival fibroblasts stress response to HEMA: A role for protein kinase C α. Cataldi A, Zara S, Rapino M, et al. J. Biomed. Mater. Res. A 101(2), 378-84, (2013)

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Antifouling foldable acrylic IOLs loaded with norfloxacin by aqueous soaking and by supercritical carbon dioxide technology. González-Chomón C, Braga ME, de Sousa HC, et al. Eur. J. Pharm. Biopharm. 82(2), 383-91, (2012)

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Effect of intermediate adhesive resin and flowable resin application on the interfacial adhesion of resin composite to pre-impregnated unidirectional S2-glass fiber bundles. Polacek P, Pavelka V, and Özcan M J. Adhes. Dent. 16(2), 155-9, (2014)

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Effect of experimental photopolymerized coatings on the hydrophobicity of a denture base acrylic resin and on Candida albicans adhesion. Lazarin AA, Machado AL, Zamperini CA, et al. Arch. Oral Biol. 58(1), 1-9, (2013)

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Fluxgate magnetorelaxometry: a new approach to study the release properties of hydrogel cylinders and microspheres. Wöhl-Bruhn S, Heim E, Schwoerer A, et al. Int. J. Pharm. 436(1-2), 677-84, (2012)

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Allergic contact dermatitis from 2-hydroxyethyl methacrylate in an adhesive on an electrosurgical earthing plate. Kanerva L and Alanko K Eur. J. Dermatol. 8(7), 521-4, (1998)

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Antiproliferative activity and apoptosis induction of Eucalyptus Citriodora resin and its major bioactive compound in melanoma B16F10 cells. Duh PD, Chen ZT, Lee SW, et al. J. Agric. Food Chem. 60(32), 7866-72, (2012)

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Effect of chemical composition on corneal cellular response to photopolymerized materials comprising 2-hydroxyethyl methacrylate and acrylic acid. Lai JY Mater. Sci. Eng. C. Mater. Biol. Appl. 33(7), 3704-10, (2013)

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Biomimetically- and hydrothermally-grown HAp nanoparticles as reinforcing fillers for dental adhesives. Wagner A, Belli R, Stötzel C, et al. J. Adhes. Dent. 15(5), 413-22, (2013)

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Preparation and evaluation of a hydrophilic poly(2-hydroxyethyl methacrylate-co-N,N'-methylene bisacrylamide) monolithic column for pressurized capillary electrochromatography. Cheng J, Chen X, Cai Y, et al. Electrophoresis 34(8), 1189-96, (2013)

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Effect of 2-hydroxyethyl methacrylate on antioxidant responsive element-mediated transcription: a possible indication of its cytotoxicity. Orimoto A, Suzuki T, Ueno A, et al. PLoS ONE 8(3), e58907, (2013)

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Infection-responsive drug delivery from urinary biomaterials controlled by a novel kinetic and thermodynamic approach. Irwin NJ, McCoy CP, Jones DS, et al. Pharm. Res. 30(3), 857-65, (2013)

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Lysozyme transport in p-HEMA hydrogel contact lenses. Bengani LC, Leclerc J, and Chauhan A J. Colloid. Interface Sci. 386(1), 441-50, (2012)

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Effects of adding barium-borosilicate glass to a simplified etch-and-rinse adhesive on radiopacity and selected properties. Martins GC, Meier MM, Loguercio AD, et al. J. Adhes. Dent. 16(2), 107-14, (2014)

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Microleakage of Class II restorations and microtensile bond strength to dentin of low-shrinkage composites. Juloski J, Carrabba M, Aragoneses JM, et al. Am. J. Dent. 26(5), 271-7, (2013)

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Intraocular lens opacification mimicking the appearance of a congenital lamellar cataract. Patel C, Hamada S, Athanasiadis Y, et al. Eye (Lond.) 26(11), 1496-8, (2012)

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Beil. 2,IV,1530

Aldrich MSDS 1, 1059:B / Corp MSDS 1 (1), 1922:D / FT-IR 1 (1), 665:B / FT-IR 2 (1), 1090:B / FT-NMR 1 (1), 1045:A / IR-Spectra (3), 390:A / IR-Spectra (2), 345:F / NMR-Reference 2 (1), 560:C / RegBook 1 (1), 753:M / Sax 6, 1344 / Sigma FT-IR 1 (2), 625:D / Structure Index 1, 116:A:9 / Vapor Phase 3, 720:D

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