| Size | Price | Stock | Qty |
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| 50mg |
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| 100mg |
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| Other Sizes |
| Targets |
Eicosapentaenoic acid methyl ester is a derivative of EPA, an omega-3 fatty acid that exerts its effects through multiple mechanisms. EPA is a precursor for resolvins, specialized pro-resolving mediators that help resolve inflammatory processes. EPA and its derivatives interact with various targets including G protein-coupled receptors (GPR120, GPR40), nuclear receptors (PPARs), and ion channels. EPA also incorporates into cell membranes, affecting membrane fluidity and signaling. As a methyl ester, the compound is a more lipophilic form of EPA, which may affect its absorption and metabolism.
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| ln Vitro |
In vitro, Eicosapentaenoic acid methyl ester has been studied for its biological activities including anti-inflammatory and immunomodulatory effects. As a degradation product of monogalactosyl diacylglycerol (an anticancer compound that induces apoptosis), EPA methyl ester may contribute to the anticancer activity of its parent compound. In cellular assays, EPA methyl ester modulates inflammatory cytokine production, reduces oxidative stress, and may induce apoptosis in cancer cells. The compound's effects are concentration-dependent and involve modulation of signaling pathways including NF-κB and MAPK.
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| ln Vivo |
In vivo, Eicosapentaenoic acid methyl ester is a metabolite of EPA and has been studied for its beneficial effects on vascular and immune physiology. EPA has been shown to reduce inflammation, improve cardiovascular health, and modulate immune responses. EPA methyl ester, as a more lipophilic form, may have different pharmacokinetic properties compared to free EPA. In animal models, EPA and its derivatives have demonstrated anti-inflammatory, cardioprotective, and immunomodulatory effects. Specific in vivo data for EPA methyl ester are limited, but its parent compound EPA is well-studied.
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| Enzyme Assay |
Non-cell-based assays for Eicosapentaenoic acid methyl ester involve analytical chemistry methods including GC-MS and LC-MS for quantification and characterization. The compound serves as an analytical standard for the quantification of EPA and its derivatives in biological samples. Its chemical properties (molecular weight 316.48, formula C₂₁H₃₂O₂) are characterized by NMR and MS. The compound's stability and degradation products are studied to understand its behavior in biological systems. Antioxidant activity may be measured by DPPH or ORAC assays.
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| Cell Assay |
Cellular assays for Eicosapentaenoic acid methyl ester are performed using various cell lines including immune cells, cancer cells, and endothelial cells. Cells are treated with EPA methyl ester at various concentrations, and cellular responses are measured. Anti-inflammatory activity is assessed by measuring pro-inflammatory cytokine production (TNF-α, IL-1β, IL-6), COX-2 expression, and NF-κB activation in LPS-stimulated macrophages. Apoptosis is assessed by Annexin V/PI staining and caspase activation in cancer cells. Cell viability is measured by MTT assays. Effects on lipid metabolism and membrane composition are evaluated.
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| Animal Protocol |
In vivo experiments with Eicosapentaenoic acid methyl ester are conducted in animal models of inflammation, cardiovascular disease, or cancer. Animals are treated with EPA methyl ester via oral administration or injection, and disease severity is assessed. In models of inflammation, inflammatory cytokine levels, tissue histology, and disease scores are measured. In cardiovascular models, lipid profiles, blood pressure, and vascular function are evaluated. In cancer models, tumor growth inhibition and survival are monitored. Pharmacodynamic markers including resolvin levels and inflammatory mediators are measured.
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| ADME/Pharmacokinetics |
Eicosapentaenoic acid methyl ester is a more lipophilic form of EPA and exhibits favorable pharmacokinetic properties. Following oral administration, the methyl ester is absorbed and hydrolyzed to free EPA by esterases in the intestine and liver. EPA is then distributed to tissues and incorporated into cell membranes. EPA is metabolized via beta-oxidation and converted to resolvins and other bioactive mediators. The compound's bioavailability, half-life, and tissue distribution have been characterized. The methyl ester form may have improved absorption compared to free EPA.
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| Toxicity/Toxicokinetics |
The toxicity of Eicosapentaenoic acid methyl ester has been evaluated in the context of omega-3 fatty acid supplementation. EPA is generally recognized as safe and well-tolerated at dietary supplementation levels. At high doses, omega-3 fatty acids may cause gastrointestinal disturbances, bleeding risk, and immunosuppression. EPA methyl ester is considered to have a favorable safety profile. Comprehensive toxicological studies including genotoxicity and organ toxicity are not specifically available for EPA methyl ester, but EPA as a compound is well-studied and considered safe for use as a dietary supplement.
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| References | |
| Additional Infomation |
cis-5,8,11,14,17-eicosapentaenoic acid methyl ester is a fatty acid methyl ester. It has been reported that cis-5,8,11,14,17-eicosapentaenoic acid methyl ester has been found in both Murrayella periclados and Marchantia polymorpha, and relevant data are available for reference.
Eicosapentaenoic acid methyl ester (CAS# 2734-47-6) is the methyl ester of eicosapentaenoic acid (EPA) with the molecular formula C₂₁H₃₂O₂ and a molecular weight of 316.48. It is a degradation product of monogalactosyl diacylglycerol, an anticancer compound that induces apoptosis. EPA methyl ester has been studied for its anti-inflammatory, immunomodulatory, and potential anticancer activities. EPA is an omega-3 fatty acid found in marine sources and serves as a precursor for resolvins that help resolve inflammatory processes. The compound is available for research use and is not approved as a therapeutic agent. |
| Molecular Formula |
C21H32O2
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|---|---|
| Molecular Weight |
316.49
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| Exact Mass |
316.24
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| CAS # |
2734-47-6
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| Related CAS # |
Eicosapentaenoic acid methyl ester-d5
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| PubChem CID |
6421261
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| Appearance |
Colorless to light yellow liquid
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| Density |
0.9±0.1 g/cm3
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| Boiling Point |
402.8±34.0 °C at 760 mmHg
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| Flash Point |
104.4±24.0 °C
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| Vapour Pressure |
0.0±0.9 mmHg at 25°C
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| Index of Refraction |
1.497
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| LogP |
6.79
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| Hydrogen Bond Donor Count |
0
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| Hydrogen Bond Acceptor Count |
2
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| Rotatable Bond Count |
14
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| Heavy Atom Count |
23
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| Complexity |
412
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| Defined Atom Stereocenter Count |
0
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| SMILES |
CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)OC
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| InChi Key |
QWDCYFDDFPWISL-JEBPEJKESA-N
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| InChi Code |
InChI=1S/C21H32O2/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21(22)23-2/h4-5,7-8,10-11,13-14,16-17H,3,6,9,12,15,18-20H2,1-2H3/b5-4-,8-7-,11-10-,14-13-,17-16-
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| Chemical Name |
methyl (5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoate
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| Synonyms |
Eicosapentaenoic acid methyl ester
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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 | 3.1597 mL | 15.7983 mL | 31.5966 mL | |
| 5 mM | 0.6319 mL | 3.1597 mL | 6.3193 mL | |
| 10 mM | 0.3160 mL | 1.5798 mL | 3.1597 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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