Page last updated: 2024-11-05

hydroxyethyl methacrylate

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

Hydroxyethyl methacrylate (HEMA) is a monomer used in the production of various polymers, most notably poly(hydroxyethyl methacrylate) (PHEMA). It is synthesized through the reaction of methacrylic acid with ethylene oxide. HEMA is a colorless, viscous liquid that is soluble in water and many organic solvents. It is commonly used as a biocompatible material in medical applications, particularly in contact lenses, dental materials, and drug delivery systems. The biocompatibility of HEMA is attributed to its ability to form hydrophilic polymers that mimic the properties of natural tissues. HEMA-based polymers are also known for their excellent mechanical properties and transparency. The study of HEMA focuses on its potential applications in biomedicine, including the development of new materials for tissue engineering, wound healing, and drug delivery. Research on HEMA aims to enhance its properties and expand its application in diverse medical fields. '

hydroxyethyl methacrylate: many of cited refs are for gel which refers to polymeric form of above cpd: POLYHYDROXYETHYL METHACRYLATE [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

2-hydroxyethyl methacrylate : An enoate ester that is the monomethacryloyl derivative of ethylene glycol. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Cross-References

ID SourceID
PubMed CID13360
CHEMBL ID1730239
CHEBI ID53709
CHEBI ID34288
SCHEMBL ID14886
MeSH IDM0046330

Synonyms (100)

Synonym
BIDD:ER0648
2-hydroxyethyl methacrylate (hema)
12676-48-1
2-propenoic acid, 2-methyl-, 2-hydroxyethyl ester
glycol methacrylate
hydroxyethyl methacrylate
nsc-24180
2-hydroxyethyl methacrylate
nsc24180
methacrylic acid, 2-hydroxyethyl ester
ethylene glycol methacrylate
glycol monomethacrylate
monomer mg-1
.beta.-hydroxyethyl methacrylate
wln: q2ovy1&u1
ethylene glycol monomethacrylate
2-(methacryloyloxy)ethanol
868-77-9
2-hydroxyethyl 2-methylprop-2-enoate
monomethacrylic ether of ethylene glycol
2-hydroxyethylmethacrylate
ethylene glycol, monomethacrylate
mhoromer
brn 1071583
nsc 24180
ccris 6879
einecs 212-782-2
2-hydroxyethyl 2-methylacrylate
hsdb 5442
hema
inchi=1/c6h10o3/c1-5(2)6(8)9-4-3-7/h7h,1,3-4h2,2h
2-hydroxyethyl methacrylate, 98%
2-hydroxyethyl methacrylate, >=99%, contains <=50 ppm monomethyl ether hydroquinone as inhibitor
NCGC00166101-01
2-hydroxyethyl methacrylate, contains <=250 ppm monomethyl ether hydroquinone as inhibitor, 97%
2-hydroxyethyl methacrylate, embedding medium (for microscopy)
CHEBI:53709
peg-ma
M0085
methacrylic acid 2-hydroxyethyl ester
phema
beta-hydroxyethyl methacrylate
1,2-ethanediol mono(2-methyl)-2-propenoate
CHEBI:34288 ,
(hydroxyethyl)methacrylate
NCGC00166101-02
unii-6e1i4iv47v
ec 212-782-2
6e1i4iv47v ,
4-02-00-01530 (beilstein handbook reference)
tox21_200415
dtxsid7022128 ,
cas-868-77-9
dtxcid202128
NCGC00257969-01
bisomer hema
1,2-ethanediol mono(2-methylpropenoate)
FT-0628271
2-hydroxyethylmethylacrylate
2-hydroxyethyl methacrylate [hsdb]
2-hydroxyethylmethacrylate (hema)
hema [inci]
2-hydroxyethyl methacrylate [who-dd]
EPITOPE ID:117123
AKOS015899920
2-hydroxyethyl(methacrylate)
hydroxyethylmethacrylate
2-hydroxylethyl methacrylate
2-methacryloyloxyethyl alcohol
hydroxyehtyl methacrylate
hydroxylethyl methacrylate
2-hydroxyetyl methacrylate
ethyleneglycol monomethacrylate
SCHEMBL14886
2-methyl-2-propenoic acid, 2-hydroxyethyl ester
1,2-ethanediol, mono(2-methyl)-2-propenyl
2-hydroxyethyl 2-methylacrylate #
CHEMBL1730239
mfcd00002863
J-509674
2-hydroxyethyl methacrylate, stabilized with 250 ppm mehq
2-hydroxyethyl methacrylate (stabilized with mehq)
2-hydroxyethyl methacrylate, (stabilized with mehq)
2-hydroxyethyl methacrylate,ophthalmic grade
DS-9647
Q424799
2-hydroxyethyl methacrylate(hema),technical grade
hydroxyethyl methacrylate(>200cp(25 degrees c))
hydroxyethyl methacrylate(5.9cp(30 degrees c))
2-hydroxyethyl methacrylate,low acid grade
D70640
CS-W013439
A904584
mfcd00081879
EN300-98188
HY-W012723
PD167321
SY279104
2-propenoic acid, 2-methyl-,2-hydroxiethyl ester
2-hema

Research Excerpts

Overview

2-Hydroxyethyl methacrylate (HEMA) is a widely used monomer of dental resin composite materials. It is a component of many resin-modified materials and elutes from dental restorations into the oral cavity.

ExcerptReferenceRelevance
"2-Hydroxyethyl methacrylate (HEMA) is a widely used monomer of dental resin composite materials. "( HEMA modulates the transcription of genes related to oxidative defense, inflammatory response and organization of the ECM in human oral cells.
Geurtsen, W; Leyhausen, G; Perduns, R; Schertl, P; Volk, J, 2019
)
1.24
"2-Hydroxyethyl methacrylate (HEMA) is a component of many resin-modified materials and elutes from dental restorations into the oral cavity. "( Effects of HEMA on Nrf2-related gene expression using a newly developed 3D co-culture model of the oral mucosa.
Geurtsen, W; Gutzki, F; Kaever, V; Perduns, R; Plum, M; Volk, J, 2019
)
1.24
"2-Hydroxyethyl methacrylate (HEMA) is a methacrylate monomer used in polymer-based dental-restorative materials. "( Cell toxicity of 2-hydroxyethyl methacrylate (HEMA): the role of oxidative stress.
Ansteinsson, V; Morisbak, E; Samuelsen, JT, 2015
)
1.47

Effects

2-Hydroxyethyl methacrylate (HEMA) has been advocated as a polymerizing solution to prevent deflation of detachable balloons in interventional neuroradiology. HEMA was added to the European baseline series in 2019.

ExcerptReferenceRelevance
"2-Hydroxyethyl methacrylate (HEMA) has been increasingly recognised as a contact allergen and was added to the European baseline series in 2019. "( 2-Hydroxyethyl methacrylate (HEMA): A clinical review of contact allergy and allergic contact dermatitis-Part 1. Introduction, epidemiology, case series and case reports.
de Groot, AC; Rustemeyer, T, 2023
)
2.35
"Hydroxyethyl methacrylate (HEMA) has been advocated as a polymerizing solution with which to prevent deflation of detachable balloons in interventional neuroradiology. "( Intracarotid hydroxyethyl methacrylate solution causing stroke in dogs.
Batjer, H; Brewer, K; Hodges, K; Purdy, P; Samson, D; White, CL, 1990
)
2.09

Treatment

2-Hydroxyethyl methacrylate treatment (3 mmol L) induced an inflammatory response in HGFs modulated by ROS production, as well as by the increase in TNF-α and COX-2 gene expression.

ExcerptReferenceRelevance
"2-hydroxyethyl methacrylate (HEMA) treatment increased the adhesion between S. "( pPKC α regulates through integrin β 1 human gingival fibroblasts/Streptococcus mitis adhesion in response to HEMA.
Cataldi, A; Cellini, L; di Giacomo, V; Di Giulio, M; Pacella, S; Pasquantonio, G; Rapino, M; Zara, S, 2013
)
1.11
"2-Hydroxyethyl methacrylate treatment (3 mmol L⁻¹) induced an inflammatory response in HGFs modulated by ROS production, as well as by the increase in TNF-α and COX-2 gene expression and by PGE₂ release."( 2-Hydroxyethyl methacrylate inflammatory effects in human gingival fibroblasts.
Cataldi, A; di Giacomo, V; Di Nisio, C; Zara, S, 2013
)
1.83

Toxicity

ExcerptReferenceRelevance
"5 or higher, a melting point well below 0 degree C, and a rat oral LD50 greater than 12."( A numerical procedure for choosing effective, low toxicity plasticizers for glycol methacrylate embedding.
Gerrits, PO; Hardonk, MJ; Horobin, RW, 1990
)
0.28
" The lack of toxicity in these specimens suggests that residual contents of inhibitor and initiator are too low to cause toxic effects on choroidal fibroblasts."( Cytotoxic effects of residual chemicals from polymeric biomaterials for artificial soft intraocular lenses.
Barrett, GD; Chirila, TV; Constable, IJ; Thompson, DE; Walker, LN, 1991
)
0.28
" The effects of 2-OH-ethyl methacrylate (HEMA), a toxic acrylic monomer, on human fibroblasts was tested."( New methods for cytotoxicity testing: quantitative video microscopy of intracellular motion and mitochondria-specific fluorescence.
Lindl, T; Maile, W; Weiss, DG,
)
0.13
" To study adverse effects on the skin in dentists possibly caused by acrylic resin-based materials."( On composite resin materials. Degradation, erosion and possible adverse effects in dentists.
Ortengren, U, 2000
)
0.31
" To study the adverse effects on skin in dentists, a questionnaire was sent to 3500 randomly selected Swedish dentists."( On composite resin materials. Degradation, erosion and possible adverse effects in dentists.
Ortengren, U, 2000
)
0.31
"The toxic effect of HgCl2 and MeHgCl from the L2 cells was about 100-700-fold higher than of the dental composite components."( Cytotoxicity of dental composite components and mercury compounds in lung cells.
Benschop, H; Durner, J; Forth, W; Hickel, R; Hume, WR; Kehe, K; Kunzelmann, KH; Reichl, FX; Spahl, W; Walther, UI, 2001
)
0.31
"5 microm) did not produce any sign of toxic reactions."( Cytotoxicity of ingredients of various dental materials and related compounds in L2- and A549 cells.
Hickel, R; Kehe, K; Liebl, B; Nilius, M; Reichl, FX; Walther, SC; Walther, UI, 2002
)
0.31
" Following the manufacturer' recommendation regarding the light-curing regime may prevent toxic effect to the pulp cells."( Effect of curing regime on the cytotoxicity of resin-modified glass-ionomer lining cements applied to an odontoblast-cell line.
Aranha, AM; de Souza Costa, CA; Giro, EM; Hebling, J; Souza, PP, 2006
)
0.33
" Although most materials are considered to be safe, adverse events occur."( Risk profiles of different injectable fillers: results from the Injectable Filler Safety Study (IFS Study).
Rzany, B; Wiest, L; Wölber, L; Zielke, H, 2008
)
0.35
"The aim of this study was to describe adverse reactions to injectable fillers based on a partly population-based case series."( Risk profiles of different injectable fillers: results from the Injectable Filler Safety Study (IFS Study).
Rzany, B; Wiest, L; Wölber, L; Zielke, H, 2008
)
0.35
"Dermatologists, plastic surgeons, and maxillofacial surgeons in Berlin were asked to report patients with adverse reactions."( Risk profiles of different injectable fillers: results from the Injectable Filler Safety Study (IFS Study).
Rzany, B; Wiest, L; Wölber, L; Zielke, H, 2008
)
0.35
"3%) areas adverse reactions occurred 12."( Risk profiles of different injectable fillers: results from the Injectable Filler Safety Study (IFS Study).
Rzany, B; Wiest, L; Wölber, L; Zielke, H, 2008
)
0.35
" We investigated the ability of a polymeric binder to reverse the toxic effects induced by gliadin in human intestinal cells and gliadin-sensitive HCD4-DQ8 mice."( Polymeric binders suppress gliadin-induced toxicity in the intestinal epithelium.
David, CS; Leroux, JC; Nasser-Eddine, M; Pinier, M; Rivard, N; Verdu, EF; Vézina, A, 2009
)
0.35
" Monomers can reach concentrations in the millimolar range, high enough to cause cellular damage, so it is justified to study their potential toxic effects."( Genotoxicity and cytotoxicity of 2-hydroxyethyl methacrylate.
Blasiak, J; Ksiazek, D; Pawlowska, E; Poplawski, T; Szczepanska, J, 2010
)
0.64
" Yet, THF showed an intermediate cytotoxicity when compared with the other solvents, being less toxic than phosphate monomer and similar to 2-hydroxyethyl methacrylate."( Tetrahydrofuran as solvent in dental adhesives: cytotoxicity and dentin bond stability.
de Carvalho, RV; de Moraes, RR; Fernández, MR; Fontes, ST; Ogliari, FA; Pinto, MB; Piva, E, 2013
)
0.59
" HEMA elicited a remarkable toxic effect."( The effect of glutathione on 2-hydroxyethylmethacrylate cytotoxicity and on resin-dentine bond strength.
Hiraishi, N; Islam, MS; Kasugai, S; Nassar, M; Ohya, K; Otsuki, M; Tagami, J; Tamura, Y; Tay, FR, 2014
)
0.4
" Mechanisms other than glutathione depletion and ROS formation seem to be of importance for the toxic effect of HEMA on lung epithelial cells."( Cell toxicity of 2-hydroxyethyl methacrylate (HEMA): the role of oxidative stress.
Ansteinsson, V; Morisbak, E; Samuelsen, JT, 2015
)
0.75
"Doxorubicin can cause life-threatening toxic effects in several organs, with cardiotoxicity being the major concern."( The minipig as a new model for the evaluation of doxorubicin-induced chronic toxicity.
Grassetti, A; Manno, RA; Nyska, A; Oberto, G; Ramot, Y, 2016
)
0.43
"All tested dental adhesives have significant adverse effects on cell viability."( Cytotoxic Effects of One-step Self-etching Dental Adhesives on Human Periodontal Ligament Fibroblasts In Vitro.
Han, N; Han, X; Mao, P; Nie, R; Shi, C; Sun, F; Wang, C, 2016
)
0.43
" The results suggested that this cell-based assay system using iNC-LCs is a potential method for in vitro screening as an alternative to animal testing to predict toxic effects of dental materials on early craniofacial development."( Cytotoxicity assay using a human pluripotent stem cell-derived cranial neural crest cell model.
Furue, MK; Mimura, S; Mine, Y; Minoda, M; Murayama, T; Nikawa, H; Suga, M, 2020
)
0.56

Compound-Compound Interactions

ExcerptReferenceRelevance
"The bonding efficacies of three commercial dentin bonding agents and an intermediate resin combined with two self-etching dentin primers (aqueous solutions of methacryloxyethyl hydrogen phenyl phosphate (Phenyl -P, 20 wt%) and either hydroxyethyl methacrylate (HEMA, 35 wt%) or glyceryl methacrylate (GM, 35 wt%)) were examined by measuring the wall-to-wall contraction gap of a light-activated resin composite in a cylindrical dentin cavity prepared in extracted human teeth."( Efficacy of dentin bonding agents combined with self-etching dentin primers containing Phenyl-P.
Hisamitsu, H; Itoh, K; Tani, C; Wakumoto, S, 1993
)
0.47

Bioavailability

ExcerptReferenceRelevance
" Nanotechnology is one of the most dynamically developing disciplines and is a powerful tool to increase the bioavailability of drugs."( [Synthesis of nanoparticles for dental drug delivery systems].
Bakó, J; Borbély, J; Hegedûs, C; Márton, I; Szepesi, M, 2007
)
0.34
" The bioavailability of such ophthalmic drugs can be enhanced significantly using contact lenses incorporating drug-loaded nanoparticles (NPs)."( Synthesis and Characterization of Poly(2-hydroxyethylmethacrylate) Contact Lenses Containing Chitosan Nanoparticles as an Ocular Delivery System for Dexamethasone Sodium Phosphate.
Behl, G; Fitzhenry, L; Iqbal, J; McLoughlin, P; O'Reilly, NJ, 2016
)
0.43
" Bioavailability of Cur is limited by its low water solubility, rapid metabolism and low stability."( Dextran based nanosized carrier for the controlled and targeted delivery of curcumin to liver cancer cells.
Anirudhan, TS, 2016
)
0.43
"In this study, sustained release superabsorbent copolymer particles have been prepared and analyzed to increase bioavailability of orally administered risedronate sodium."( RELATIVE BIOAVAILABILITY OF RISEDRONATE SODIUM ADMINISTERED IN SUPERABSORBENT COPOLYMER PARTICLES VERSUS ORAL SOLUTION TO NORMAL HEALTHY RABBITS.
Abbas, N; Bukhari, NI; Hussain, T; Karim, S; Shahzad, MK, 2016
)
0.43

Dosage Studied

ExcerptRelevanceReference
" However, it levelled off at 7% when the total dosage reached 1 Mrad."( Preparation and properties of a biomaterial: HEMA grafted SBS by gamma-ray irradiation.
Hsiue, GH; Wu, RL; Yang, JM, 1988
)
0.27
" Control gels without incorporated antibodies did not bind radiolabeled methotrexate, whereas a dose-response curve expressing percent bound methotrexate against antiserum concentration could be readily constructed for appropriate gels."( Radioimmunoassay for methotrexate using hydroxyethylmethacrylate hydrogel.
Franzblau, C; Franzblau, W; Lopez, JA; Mutkoski, R; Tracey, KJ, 1983
)
0.27
"Three types of sustained and controlled release dosage forms of sodium fluoride (NaF) for the prevention of dental caries are reviewed."( The use of controlled and sustained release agents in dentistry: a review of applications for the control of dental caries.
Mirth, DB, 1980
)
0.26
" Concentrations leading to 50% cell survival (TC50 values) were calculated from fitted dose-response curves."( Responses of L929 mouse fibroblasts, primary and immortalized bovine dental papilla-derived cell lines to dental resin components.
Hiller, KA; Schmalz, G; Schweikl, H; Thonemann, B, 2002
)
0.31
" Comparisons were made by constructing dose-response curves for each type of monocyte and the four components."( Human peripheral blood monocytes versus THP-1 monocytes for in vitro biocompatibility testing of dental material components.
Heil, TL; Lockwood, PE; Volkmann, KR; Wataha, JC, 2002
)
0.31
" A comparable number of teeth required repeat dosage in both groups."( 2% sodium fluoride-iontophoresis compared to a commercially available desensitizing agent.
Gupta, R; Pandit, N; Singal, P, 2005
)
0.33
"5 days delivering a therapeutically relevant dosage and was fit to a power law model indicating zero-order release characteristics with n=0."( Zero-order therapeutic release from imprinted hydrogel contact lenses within in vitro physiological ocular tear flow.
Ali, M; Byrne, ME; Hong, JW; Horikawa, S; Saha, J; Venkatesh, S, 2007
)
0.34
"Half maximum effect concentrations (EC(50)) were determined based on the dose-response curves derived by xCELLigence measurements."( Real-time xCELLigence impedance analysis of the cytotoxicity of dental composite components on human gingival fibroblasts.
Haertel, U; Hickel, R; Reichl, FX; Scherthan, H; Styllou, M; Urcan, E, 2010
)
0.36
"Most treatments for diabetic eye conditions rely on systemic (oral) or intravitreal administration, and there is still a demand of efficient and comfortable ocular dosage forms."( Epalrestat-loaded silicone hydrogels as contact lenses to address diabetic-eye complications.
Alvarez-Lorenzo, C; Alvarez-Rivera, F; Concheiro, A, 2018
)
0.48
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (2)

RoleDescription
polymerisation monomerAny compound used as a monomer for a polymerisation process. The term is generally used in relation to industrial polymerisation processes.
allergenA chemical compound, or part thereof, which causes the onset of an allergic reaction by interacting with any of the molecular pathways involved in an allergy.
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Drug Classes (1)

ClassDescription
enoate esterAn alpha,beta-unsaturated carboxylic ester of general formula R(1)R(2)C=CR(3)-C(=O)OR(4) (R(4) =/= H) in which the ester C=O function is conjugated to a C=C double bond at the alpha,beta position.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Protein Targets (5)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
RAR-related orphan receptor gammaMus musculus (house mouse)Potency0.00200.006038.004119,952.5996AID1159521
GLI family zinc finger 3Homo sapiens (human)Potency28.00170.000714.592883.7951AID1259369
retinoic acid nuclear receptor alpha variant 1Homo sapiens (human)Potency15.74650.003041.611522,387.1992AID1159552
pregnane X nuclear receptorHomo sapiens (human)Potency62.68800.005428.02631,258.9301AID1346982
histone acetyltransferase KAT2A isoform 1Homo sapiens (human)Potency39.81070.251215.843239.8107AID504327
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (1,724)

TimeframeStudies, This Drug (%)All Drugs %
pre-1990161 (9.34)18.7374
1990's342 (19.84)18.2507
2000's498 (28.89)29.6817
2010's619 (35.90)24.3611
2020's104 (6.03)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 60.52

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be very strong demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index60.52 (24.57)
Research Supply Index7.55 (2.92)
Research Growth Index4.82 (4.65)
Search Engine Demand Index104.29 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (60.52)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials72 (3.96%)5.53%
Reviews30 (1.65%)6.00%
Case Studies40 (2.20%)4.05%
Observational2 (0.11%)0.25%
Other1,675 (92.08%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]