| Size | Price | Stock | Qty |
|---|---|---|---|
| 100g |
|
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| 200g |
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Purity: ≥98%
| Targets |
The molecular targets of HEMA are not biological targets in the context of pharmacological activity, as the compound is a monomer used in polymer synthesis rather than a therapeutic agent. In dental applications, HEMA functions as a desensitizing agent by physically blocking dentinal tubules through polymerization upon application, rather than through specific molecular interactions. The compound's hydroxyl and methacrylate groups allow it to polymerize rapidly under appropriate conditions, forming a polymer network that seals the dentin surface and prevents fluid movement within the tubules, which is the mechanism of dentin hypersensitivity. In biomedical applications, HEMA is used as a building block for hydrogels that can encapsulate drugs, cells, or other bioactive molecules. The compound does not interact with specific receptors or enzymes in vivo but may have some biological effects due to its chemical reactivity, including potential cytotoxicity and sensitization.
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|---|---|
| ln Vitro |
In vitro activity of HEMA is primarily related to its use in the synthesis of hydrogels and other biomaterials. In polymer chemistry assays, HEMA is evaluated for its polymerization kinetics, conversion efficiency, and compatibility with other monomers. The compound's activity in dental applications is assessed by measuring the reduction in dentin permeability after treatment with HEMA-containing formulations, using hydraulic conductance measurements. In cell culture studies, HEMA has been shown to exhibit concentration-dependent cytotoxicity, with effects on cell viability, proliferation, and morphology. The compound can induce oxidative stress and apoptosis in various cell types, including fibroblasts and keratinocytes, at concentrations above 1-10 mM. HEMA is also used in drug delivery studies, where it serves as a hydrophilic component of hydrogels for the controlled release of therapeutic agents. Specific IC50 values for HEMA against biological targets are not applicable, as it is not a pharmacologically active compound.
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| ln Vivo |
In vivo activity of HEMA is related to its use in biomedical devices and dental materials rather than as a therapeutic agent. In dental applications, HEMA-containing adhesives and desensitizing agents are applied topically to tooth surfaces, where they polymerize in situ to form a protective barrier. The compound's in vivo effects are primarily physical, sealing dentinal tubules and reducing hypersensitivity. In animal models, HEMA has been evaluated for its biocompatibility as a component of implantable devices, with studies assessing tissue response, inflammation, and fibrosis. In preclinical studies, HEMA-based hydrogels have been used for drug delivery, tissue engineering, and wound healing applications. The compound's in vivo efficacy depends on the specific application and the formulation used. However, HEMA itself is not administered as a drug and does not produce systemic pharmacological effects. Residual monomer can leach from polymerized materials and cause local tissue irritation.
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| Enzyme Assay |
For in vitro polymerization and material characterization assays with HEMA, the following protocol is used: HEMA is purified by distillation or by passing through an inhibitor-removal column to remove the polymerization inhibitor (MEHQ). For hydrogel synthesis, HEMA is mixed with a crosslinker (e.g., ethylene glycol dimethacrylate, 0.1-2 mol%) and a photoinitiator (e.g., Irgacure 2959, 0.5-1 wt%) in water or a water-ethanol mixture. The solution is degassed by nitrogen purging and polymerized by exposure to UV light (365 nm, 5-10 mW/cm²) for 10-60 minutes or by thermal initiation at 40-60°C. The resulting hydrogel is washed with distilled water to remove unreacted monomers and dried to constant weight. The swelling ratio is determined by immersing the hydrogel in water at 37°C and measuring the weight gain over time. The mechanical properties are assessed by compression or tensile testing. For drug release studies, a model drug is incorporated into the hydrogel during synthesis, and the release kinetics are monitored by UV spectroscopy or HPLC.
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| Cell Assay |
For in vitro cell-based assays with HEMA, the following typical protocol is used: Human gingival fibroblasts (HGFs) or other cell lines are cultured in DMEM with 10% FBS and antibiotics at 37°C in 5% CO₂. Cells are seeded in 96-well plates at 5,000-10,000 cells per well and allowed to adhere overnight. HEMA is dissolved in culture medium to final concentrations ranging from 0.01 to 20 mM (with the final concentration of any co-solvent ≤ 0.1%). Cells are treated for 24-72 hours, and cell viability is assessed using the MTT or CellTiter-Glo assay to determine the IC50. For assessment of oxidative stress, cells are loaded with DCFH-DA and fluorescence is measured. Apoptosis is assessed by Annexin V-FITC/PI staining and flow cytometry. For assessment of cell morphology, cells are stained with phalloidin for actin filaments and observed by fluorescence microscopy. For dentin desensitization studies, extracted human teeth are prepared and treated with HEMA-containing formulations, and dentin permeability is measured using a hydraulic conductance apparatus.
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| Animal Protocol |
For in vivo animal studies with HEMA-based materials, the following general protocol is used: For biocompatibility testing, male Sprague-Dawley rats (8-10 weeks old, 200-250 g) are anesthetized, and HEMA-based hydrogel or polymer samples are implanted subcutaneously in the dorsal region. Animals are monitored for clinical signs, body weight changes, and local tissue reactions for 7, 14, and 28 days post-implantation. At the end of the study, animals are euthanized, and the implant sites are excised for histopathological examination (H&E staining) to assess inflammation, fibrosis, and tissue integration. For dental applications, HEMA-containing adhesives are applied to tooth surfaces in animal models, and the teeth are extracted for histological analysis. For drug delivery studies, animals are administered HEMA-based hydrogels containing a therapeutic agent, and the pharmacokinetics and efficacy of the drug are evaluated. Blood samples are collected for hematological and biochemical analysis.
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| ADME/Pharmacokinetics |
Metabolism / Metabolites
Small amounts of methacrylates can be rapidly metabolized into alcohols and methacrylic acid through saponification. The latter can form acetyl-CoA derivatives, which then enter the normal lipid metabolism pathway. /Methacrylates/ The pharmacokinetic properties of HEMA are not characterized in the context of systemic administration, as the compound is a monomer used in polymer synthesis and is not intended for use as a therapeutic agent. When used in dental or biomedical applications, any unreacted HEMA that leaches from the polymerized material may be absorbed locally, but systemic absorption is minimal. HEMA is metabolized by esterases to methacrylic acid and ethylene glycol, which are further metabolized and excreted. The compound has a low molecular weight (130.14 g/mol) and is hydrophilic, suggesting that it would have limited membrane permeability and would be rapidly cleared if absorbed systemically. The half-life of HEMA in biological systems is expected to be short due to rapid metabolism and excretion. However, comprehensive pharmacokinetic studies are not available for HEMA due to its status as a polymer precursor rather than a drug. |
| Toxicity/Toxicokinetics |
Non-Human Toxicity Values
Intraperitoneal LD50 in mice: 0.497 mL/kg Oral LD50 in mice: 5.1 mL/kg Oral LD50 in rats: 11.2 g/kg Dermal LD50 in rabbits: > 3.0 g/kg For more complete non-human toxicity data on 2-hydroxyethyl methacrylates (7 in total), please visit the HSDB record page. The toxicity profile of HEMA is well-documented due to its widespread use in dental and biomedical applications. HEMA is a known skin sensitizer and can cause allergic contact dermatitis in sensitized individuals. In in vitro studies, HEMA exhibits concentration-dependent cytotoxicity, with IC50 values typically in the range of 1-10 mM for various cell lines. The compound induces oxidative stress, DNA damage, and apoptosis at higher concentrations. In animal studies, HEMA has been shown to cause local tissue irritation and inflammation at the site of application or implantation. The compound is not classified as a carcinogen or mutagen, but it has been shown to be genotoxic in some in vitro assays at high concentrations. In dental applications, the amount of HEMA that leaches from polymerized materials is generally low and considered safe for clinical use. However, patients with known allergies to methacrylates should avoid HEMA-containing products. |
| Additional Infomation |
2-Hydroxyethyl methacrylate is an acrylate ester, a monomethacrylyl derivative of ethylene glycol. It is both a polymer monomer and an allergen. Its function is related to ethylene glycol and methacrylic acid. 2-Hydroxyethyl methacrylate is a hydroxy ester compound and also a resin monomer used for dentin desensitization. Topical application of 2-hydroxyethyl methacrylate to sensitive teeth can seal the sensitive areas and block the dentinal tubules on the dentin surface from stimuli that cause pain. This prevents stimulation of the dental nerve, thereby relieving pain caused by tooth sensitivity. See also: Phemfilcon A (monomer); Senofilcon A (monomer); Hioxifilcon A (monomer)... See more...
2-Hydroxyethyl methacrylate (HEMA) (CAS# 868-77-9) is a hydrophilic methacrylate monomer with a molecular formula of C6H10O3 and a molecular weight of 130.14 g/mol. It is the first monomer used to synthesize hydrogels for biomedical applications. HEMA is used as a resin monomer for dentin desensitization and in drug delivery systems. Future research could focus on developing HEMA-based materials with improved biocompatibility and reduced cytotoxicity, exploring new applications in tissue engineering and regenerative medicine, and developing safer alternatives for dental and biomedical use. |
| Molecular Formula |
C6H10O3
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|---|---|
| Molecular Weight |
130.1418
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| Exact Mass |
130.062
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| CAS # |
868-77-9
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| Related CAS # |
25249-16-5;9016-69-7;25736-86-1
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| PubChem CID |
13360
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| Appearance |
Clear mobile liquid
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| Density |
1.1±0.1 g/cm3
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| Boiling Point |
189.0±0.0 °C at 760 mmHg
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| Melting Point |
-12 °C
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| Flash Point |
97.2±0.0 °C
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| Vapour Pressure |
0.2±0.7 mmHg at 25°C
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| Index of Refraction |
1.443
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| LogP |
0.5
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| Hydrogen Bond Donor Count |
1
|
| Hydrogen Bond Acceptor Count |
3
|
| Rotatable Bond Count |
4
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| Heavy Atom Count |
9
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| Complexity |
118
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| Defined Atom Stereocenter Count |
0
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| SMILES |
O=C(C(C)=C)OCCO
|
| InChi Key |
WOBHKFSMXKNTIM-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C6H10O3/c1-5(2)6(8)9-4-3-7/h7H,1,3-4H2,2H3
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| Chemical Name |
2-hydroxyethyl 2-methylprop-2-enoate
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: This product requires protection from light (avoid light exposure) during transportation and storage. |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
DMSO : ≥ 100 mg/mL (~768.40 mM)
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|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (19.21 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (19.21 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. View More
Solubility in Formulation 3: ≥ 2.5 mg/mL (19.21 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 7.6840 mL | 38.4202 mL | 76.8403 mL | |
| 5 mM | 1.5368 mL | 7.6840 mL | 15.3681 mL | |
| 10 mM | 0.7684 mL | 3.8420 mL | 7.6840 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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