| Size | Price | |
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| Other Sizes |
Purity: ≥98%
| Targets |
The molecular targets of Ethylene glycol dimethacrylate are not biological targets in the context of therapeutic activity, as the compound is a cross-linking agent used in polymer chemistry rather than a pharmaceutical agent. In polymerization reactions, EGDMA functions as a difunctional monomer that forms crosslinks between polymer chains, creating three-dimensional network structures. The compound's two methacrylate groups allow it to participate in free radical polymerization, forming covalent bonds with growing polymer chains and linking them together. This cross-linking increases the mechanical strength, thermal stability, and chemical resistance of the resulting polymer. In biological systems, EGDMA does not have specific molecular targets but can interact with cellular components through its reactive methacrylate groups, leading to cytotoxicity and genotoxicity. The compound can induce oxidative stress by increasing ROS production, leading to DNA damage, apoptosis, and cell cycle arrest in G1/G0 phase.
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| ln Vitro |
In vitro activity of Ethylene glycol dimethacrylate is characterized by its effects on cells and its use as a cross-linking agent. In human gingival fibroblasts (HGFs), EGDMA exhibits cytotoxic and genotoxic effects, increasing intracellular ROS production, causing DNA damage, and inducing apoptosis. The compound also increases the expression of GPx4 and SOD2, which are antioxidant enzymes involved in the cellular response to oxidative stress. In polymer chemistry assays, EGDMA is evaluated for its cross-linking efficiency, compatibility with various monomers, and its effect on the mechanical and thermal properties of polymers. The compound's cross-linking activity is assessed by measuring the gel fraction, swelling ratio, and mechanical properties of the resulting polymers. In cell culture, EGDMA is typically used at concentrations of 0.1-10 mM to study its cytotoxic effects. The compound's IC50 for cytotoxicity in various cell lines is typically in the low millimolar range.
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| ln Vivo |
In vivo activity of Ethylene glycol dimethacrylate is not characterized as a therapeutic effect, as the compound is a chemical cross-linking agent used in polymer synthesis and is not intended for administration to living organisms. However, in toxicological studies, EGDMA has been evaluated for its potential adverse effects. In animal models, EGDMA exposure has been associated with local tissue irritation and inflammation at the site of application. The compound's ability to induce oxidative stress and DNA damage raises concerns about its potential genotoxicity and carcinogenicity in vivo. However, comprehensive in vivo studies are limited. In biomedical applications, EGDMA is used as a cross-linker in polymer-based drug delivery systems, tissue engineering scaffolds, and dental materials. In these applications, any unreacted EGDMA that leaches from the polymerized material may cause local toxicity. The compound is not used as a therapeutic agent and does not produce systemic pharmacological effects.
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| Enzyme Assay |
For in vitro cross-linking and polymerization assays with Ethylene glycol dimethacrylate, the following protocol is used: EGDMA is mixed with a monomer (e.g., methyl methacrylate or 2-hydroxyethyl methacrylate) at concentrations of 0.1-5 mol%. A free radical initiator (e.g., AIBN or benzoyl peroxide, 0.1-1 wt%) is added, and the mixture is degassed by nitrogen purging. Polymerization is carried out at 60-80°C for 2-24 hours in a sealed tube or mold. The resulting polymer is characterized by determining the gel fraction (the insoluble portion after extraction with a solvent), the swelling ratio in a suitable solvent, and the mechanical properties (compressive strength, flexural strength, modulus). The cross-linking density is calculated using the Flory-Rehner equation from the swelling data. For kinetic studies, the polymerization is monitored by differential scanning calorimetry (DSC) to measure the heat of polymerization and the conversion rate. For cell culture studies, polymer samples are extracted in culture medium for 24-72 hours, and the extract is used to treat cells for cytotoxicity assessment.
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| Cell Assay |
For in vitro cell-based assays with Ethylene glycol dimethacrylate, 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. EGDMA is dissolved in DMSO and diluted in culture medium to final concentrations ranging from 0.01 to 10 mM (final DMSO ≤ 0.1%). Cells are treated for 24-72 hours. 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 (10 μM) and fluorescence is measured at excitation 485 nm and emission 535 nm. For assessment of apoptosis, cells are stained with Annexin V-FITC and propidium iodide and analyzed by flow cytometry. For cell cycle analysis, cells are fixed in 70% ethanol, stained with propidium iodide, and analyzed by flow cytometry. For assessment of DNA damage, the comet assay is performed: cells are embedded in agarose, lysed, and subjected to electrophoresis, and DNA damage is quantified by measuring comet tail length or tail moment. For assessment of antioxidant enzyme expression, cells are lysed and GPx4 and SOD2 protein levels are measured by Western blotting or ELISA.
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| Animal Protocol |
For in vivo animal studies with Ethylene glycol dimethacrylate, the following general protocol is used for biocompatibility and toxicity assessment: Male Sprague-Dawley rats (8-10 weeks old, 200-250 g) are anesthetized, and EGDMA-containing 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 necrosis. For systemic toxicity assessment, animals are administered EGDMA orally or intraperitoneally at doses of 10-100 mg/kg, and clinical signs, mortality, and body weight changes are monitored for 14 days. Blood samples are collected for hematological and biochemical analysis (ALT, AST, BUN, creatinine). Organs (liver, kidney, heart, lung, brain) are collected for histopathological examination and for measurement of oxidative stress markers (MDA, GSH, SOD).
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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 Ethylene glycol dimethacrylate are not characterized, as the compound is a chemical cross-linking agent used in polymer chemistry and is not intended for systemic administration. EGDMA is a small, hydrophobic molecule (molecular weight 198.22 g/mol) with low aqueous solubility. If absorbed systemically, EGDMA would be expected to be metabolized by esterases to methacrylic acid and ethylene glycol, which are further metabolized and excreted. The compound's half-life in biological systems is expected to be short due to rapid hydrolysis and metabolism. However, comprehensive pharmacokinetic studies are not available for EGDMA due to its status as a chemical reagent rather than a drug. In biomedical applications, the amount of unreacted EGDMA that leaches from polymerized materials is typically low and is rapidly cleared from the body. |
| Toxicity/Toxicokinetics |
The toxicity profile of Ethylene glycol dimethacrylate is characterized by its cytotoxic and genotoxic effects. In vitro, EGDMA induces oxidative stress, DNA damage, apoptosis, and cell cycle arrest in various cell lines. The compound increases intracellular ROS production and upregulates antioxidant enzymes such as GPx4 and SOD2. In animal studies, EGDMA has been shown to cause local tissue irritation and inflammation at the site of implantation. The compound is not classified as a carcinogen, but its genotoxic potential raises concerns about long-term exposure. EGDMA is a skin and respiratory irritant and should be handled with appropriate safety precautions in a fume hood with personal protective equipment. The compound should be stored in a cool, dry place away from heat and light. In case of ingestion or skin contact, medical attention should be sought immediately.
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| Additional Infomation |
Ethylene glycol dimethacrylate is a 1,2-bis(methacryloyl) derivative of ethylene glycol, and is an acrylate ester. It can be used as a crosslinking agent, polymerizing monomer, and allergen. Its function is related to ethylene glycol and methacrylic acid. Ethylene glycol dimethacrylate has been reported to be found in Bletilla striata, and relevant data are available. Ethylene glycol dimethacrylate is an organic compound and an ester of methacrylic acid. It is an active resin that can be used as a crosslinking agent in the production of functional monomers and polymers. Through photopolymerization, this reagent can be used as a component of hydrogels for applications such as tissue engineering scaffolds or drug delivery carriers. In turn, hydrogel products can be used to prevent thrombosis, postoperative adhesions, and as coatings for biosensors. See also: Hioxifilcon A (monomer); Harufilcon A (monomer); Abafilcon A (monomer)... See more...
Ethylene glycol dimethacrylate (EGDMA) (CAS# 97-90-5) is a diester cross-linking agent for polymers with a molecular formula of C10H14O4 and a molecular weight of 198.22 g/mol. It is widely used as a functional monomer and cross-linker in free radical copolymerization. EGDMA increases apoptosis, GPx4, SOD2, and ROS, and is cytotoxic and genotoxic. Future research could focus on developing safer cross-linking agents with reduced cytotoxicity and genotoxicity for biomedical applications, investigating the long-term biocompatibility of EGDMA-containing materials, and developing strategies to minimize the release of unreacted monomers from polymerized materials. |
| Molecular Formula |
C10H14O4
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|---|---|
| Molecular Weight |
198.2158
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| Exact Mass |
198.089
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| CAS # |
97-90-5
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| Related CAS # |
25721-76-0;9051-34-7;25852-47-5
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| PubChem CID |
7355
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| Appearance |
Colorless to light yellow liquid（Density：1.051 g/cm3）
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| Density |
1.0±0.1 g/cm3
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| Boiling Point |
260.6±13.0 °C at 760 mmHg
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| Melting Point |
-40 °C
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| Flash Point |
121.8±18.2 °C
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| Vapour Pressure |
0.0±0.5 mmHg at 25°C
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| Index of Refraction |
1.449
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| LogP |
2.78
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| Hydrogen Bond Donor Count |
0
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| Hydrogen Bond Acceptor Count |
4
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| Rotatable Bond Count |
7
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| Heavy Atom Count |
14
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| Complexity |
237
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| Defined Atom Stereocenter Count |
0
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| SMILES |
O=C(C(C)=C)OCCOC(C(C)=C)=O
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| InChi Key |
STVZJERGLQHEKB-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C10H14O4/c1-7(2)9(11)13-5-6-14-10(12)8(3)4/h1,3,5-6H2,2,4H3
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| Chemical Name |
2-(2-methylprop-2-enoyloxy)ethyl 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 |
| 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) |
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
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| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 5.0449 mL | 25.2245 mL | 50.4490 mL | |
| 5 mM | 1.0090 mL | 5.0449 mL | 10.0898 mL | |
| 10 mM | 0.5045 mL | 2.5224 mL | 5.0449 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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