Product name: Eicosapentaenoic acid
Synonym name: EPA; cis-5,8,11,14,17-Eicosapentaenoic acid；Timnodonic acid;
Catalogue No.: BP4141
Cas No.: 10417-94-4
Formula: C20H30O2
Mol Weight: 302.458
Botanical Source:
Physical Description:
Type of Compound: Aliphatics
Purity: 95%~99%
Analysis Method: HPLC or/and GC
Identification Method: Mass, NMR
Packing: Brown vial or HDPE plastic bottle
Storage: Store in a well closed container, protected from air and light. Put into refrigerate or freeze for long term storage.
Whenever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20℃. Generally, these will be useable for up to two weeks.
The product could be supplied from milligrams to grams
Inquire for bulk scale.
For Reference Standard and R&D, Not for Human Use Directly.
HPLC of Eicosapentaenoic acid
HNMR of Eicosapentaenoic acid
Storage conditions：Short-term storage at 2~8℃, long-term storage at -20 ~ -80℃
37.3000
5.9936
3.6180
.0080
4.9123
2.7942
High
96.1827
3.0372
Yes
Yes
No
No
No
No
0.0
No
Yes
Yes
Yes
Eicosapentaenoic acid (EPA) is a typical omega-3 long-chain polyunsaturated fatty acid (ω-3 LC-PUFAs), widely found in deep-sea fish and some seaweeds. As one of the representative essential fatty acids for the human body, EPA has attracted widespread attention in recent years due to its diverse biological functions and significant pharmacological activity, especially in cardiovascular diseases, inflammation regulation, and tumor suppression. EPA is not only widely used as a dietary supplement, but its mechanisms of action at the molecular level are gradually being elucidated, especially demonstrating unique advantages in regulating gene expression, signaling pathways, and cellular functions. This paper will systematically review the chemical structure and physicochemical properties, sources and extraction methods, pharmacological activity, mechanism of action, druggability evaluation, and clinical application prospects of EPA, aiming to provide researchers in the field of natural product pharmacology with comprehensive and in-depth reference.
EPA's chemical name is eicosapentaenoic acid, molecular formula C20H30O2, and molecular weight 302.4580. Its structural features include 20 carbon atoms and 5 cis double bonds, with the double bonds located at 5, 8, 11, 14, and 17 carbon atoms respectively, making it a typical ω-3 polyunsaturated fatty acid. In the molecular structure of EPA, the methyl side chain at the end forms a typical fatty acid backbone with the carboxyl terminus, and the presence of double bonds gives it high chemical reactivity and biological functions.
In terms of physicochemical properties, EPA's LogP value is 5.9936, indicating strong lipophilus. It is poorly soluble in water (about 0.0080), which matches its long-chain fatty acid properties. Its polar surface area (TPSA) is 37.3 Ų, indicating that the molecule has certain polar groups, but overall it is still predominantly hydrophobic. EPA can cross the blood-brain barrier (BBB), laying the foundation for its potential applications in central nervous system diseases. Importantly, EPA did not show hERG channel inhibition, and Ames-induced mutagenic tests were negative, indicating a relatively high safety.
EPA is mainly found in marine organisms, especially deep-sea fish (such as salmon, herring, cod) and certain seaweed. Although EPA is present in low amounts in the plant kingdom, certain microalgae such as diatoms and red algae can also synthesize EPA, making it a sustainable biological resource.
Traditional EPA extraction methods include:
Solvent extraction method: Fatty acids are extracted from fish oil or algal oil using organic solvents such as ether and hexane, followed by saponification and esterification steps to separate and purify EPA.
Supercritical CO2 Extraction: Using supercritical carbon dioxide as the extractant, it is mild and environmentally friendly, effectively extracting high-purity EPA while avoiding thermal degradation.
Enzymatic hydrolysis: Uses lipase to selectively hydrolyze fatty acid esters in fish oil, enriching EPA, suitable for industrial-scale production.
Fermentation method: EPA is produced through engineering-modified microalgae or microbial fermentation, offering advantages such as strong controllability and environmental friendliness.
In recent years, with the development of biotechnology, research on genetically engineered microalgae producing EPA has increased, providing new ideas for sustainable EPA supply.
As an important member of omega-3 fatty acids, EPA exhibits various pharmacological activities, mainly covering cardiovascular protection, anti-inflammatory, anti-tumor, and neuroprotective aspects.
EPA can significantly improve lipid profile, lower triglyceride levels, decrease LDL oxidation, inhibit platelet aggregation, and promote enhanced vascular endothelial function. Research shows that EPA exerts protective effects by regulating various cardiovascular-related targets (such as SELP, PPARG, ACE, AKT1, ADRB2, KCNH2, NOS3, ICAM1, VCAM1, SLC8A1), reducing the risk of atherosclerosis and myocardial infarction.
EPA is a precursor to inflammatory mediators such as prostaglandins and leukotrienes, whose metabolites have anti-inflammatory and immunomodulatory functions. EPA can inhibit the expression of pro-inflammatory cytokines (such as TNF-α and IL-6), reduce inflammatory responses, and alleviate pathological progression of chronic inflammation-related diseases.
EPA promotes the reexpression of the tumor suppressor gene CCAAT/enhancer-binding protein δ (C/EBPδ), exerts DNA demethylation effects, and regulates tumor cell proliferation and apoptosis. Additionally, EPA demethylates U937 leukemia cells via H-RAS intron 1 CpG islands, activating the RAS/ERK/C/EBPβ signaling pathway, inducing cell differentiation, and inhibiting malignant transformation.
EPA promotes relaxation of vascular smooth muscle cells, enhances vasodilatory responses, and improves hemodynamics. This effect helps lower blood pressure and alleviates vascular damage associated with hypertension.
The biological effects of EPA depend on its regulation of intracellular signaling pathways and gene expression, with the specific mechanisms as follows:
DNA demethylation regulates gene expression
EPA can mediate DNA demethylation, promote reexpression of tumor suppressor genes C/EBPδ, and restore its function of suppressing tumor proliferation. Additionally, EPA activates the RAS/ERK/C/EBPβ signaling pathway by demethylating the H-RAS intron 1 CpG island, regulating the differentiation and proliferation of leukemia cells.
Regulation of cardiovascular-related targets
EPA acts on various cardiovascular targets, including selector (SELP), peroxisome proliferator-activated receptor γ (PPARG), angiotensin-converting enzyme (ACE), protein kinase B (AKT1), β2 adrenergic receptor (ADRB2), potassium channel (KCNH2), endothelial nitric oxide synthase (NOS3), intercellular adhesion molecule 1 (ICAM1), vascular cell adhesion molecule 1 (VCAM1), and sodium-calcium exchange protein (SLC8A1). By regulating these targets, EPA improves vascular function, suppresses inflammatory responses, and prevents thrombosis.
Regulation of anti-inflammatory signaling pathways
EPA metabolites such as eicosatrienoic acid (E-series resolvins) can inhibit the NF-κB signaling pathway, reduce the release of inflammatory mediators, and regulate immune cell function.
Vascular smooth muscle cells relax
EPA activates endothelial NOS3, promotes nitric oxide (NO) production, induces relaxation of vascular smooth muscle cells, and enhances vasodilation.
EPA's druggability parameters indicate its promising potential for drug development. Its molecular weight is moderate (302.4580), but its high LogP value (5.9936) and low water solubility (0.0080) suggest strong lipid solubility, and oral formulations require optimized solubility and bioavailability. EPA can cross the blood-brain barrier, giving it potential applications in neurological diseases.
In terms of safety, EPA did not show hERG channel inhibition, reducing the risk of arrhythmias. A negative Ames test indicates no significant mutagenicity and good safety.
Pharmacokinetic studies show that EPA is effectively absorbed after oral administration, existing in plasma as bound to free fatty acids and phospholipids. EPA is mainly metabolized in the body through β-oxidative metabolism, has a long half-life, and has the ability to act sustainably. Its metabolites include various bioactive lipid mediators involved in regulating inflammation and immune responses.
Clinically, EPA is mainly used as an adjunct therapy for cardiovascular diseases, especially in reducing hypertriglyceridemia, preventing atherosclerosis, and myocardial infarction. Multiple clinical trials support that EPA supplements can reduce the incidence of cardiovascular events and improve patient outcomes.
In addition, EPA shows broad application prospects in anti-inflammation, anti-tumor, and neuroprotective fields. By regulating gene methylation and signaling pathways, it may become an adjunct drug in tumor treatment. EPA's relaxing effect on vascular smooth muscle cells also suggests its potential in hypertension and vascular dysfunction diseases.
In the future, with the development of nanotechnology and drug delivery systems, the bioavailability and targeting of EPA are expected to further improve. Technological advances in genetically engineered microalgae for EPA production will drive its sustainable supply and large-scale application. Furthermore, in-depth analysis of EPA's molecular mechanisms of action and its synergistic effects with other fatty acids will provide a theoretical foundation for developing novel compound fatty acid drugs.
Eicosapentaenoic acid (EPA), as an important omega-3 long-chain polyunsaturated fatty acid, demonstrates significant pharmacological effects in cardiovascular protection, anti-inflammation, anti-tumor, and vasodilatory effects due to its unique chemical structure and diverse biological activities. By regulating DNA methylation, signaling pathways, and various molecular targets, it exerts complex and delicate biological regulatory functions. EPA's excellent safety and druggability parameters have laid a solid foundation for its clinical application. In the future, as research on extraction technologies, drug formulations, and molecular mechanisms continues to deepen, EPA is expected to become an important research and application target in the field of natural product pharmacology, driving progress in the prevention and treatment of related diseases.
