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Eicosapentaenoic Acid is used in combination with docosahexaenoic acid (DHA) for comprehensive omega-3 therapy.
Eicosapentaenoic Acid is applied in medical nutrition therapy for patients with high cardiovascular risk.
Eicosapentaenoic Acid is widely used to support cardiovascular health by reducing triglyceride levels.
CAS Number: 10417-94-4
EC / EINECS Number: (not always listed in standard chemical inventories for pure nutrient compounds, though entries exist e.g., 600-528-7 under German database classifications)
Molecular Formula: C₂₀H₃₀O₂
Molecular Weight: 302.45 g/mol
SYNONYMS:
(5Z,8Z,11Z,14Z,17Z)-Icosa-5,8,11,14,17-pentaenoic acid, (5Z,8Z,11Z,14Z,17Z)-5,8,11,14,17-eicosapentaenoic acid, all cis-5,8,11,14,17-Eicosapentaenoic Acid, icosapentaenoic acids, eicosapentaenoic acids, Acid, Eicosapentanoic, RefChem:5788, omega 3 Eicosapentaenoic Acid, omega-3-Eicosapentaenoic Acid, CHEBI:36006, DTXSID901018009, C20:5, 20:5, 25378-27-2, Eicosapentaenoic Acid, Eicosapentanoic Acid, Icosapentaenoic Acid, (5E,8E,11E,14E,17E)-icosa-5,8,11,14,17-pentaenoic acid, EPA, Timnodonic acid, Eicosapentaenoic, SCHEMBL120666, CHEMBL4802124, CHEBI:92823, AKOS015893005, Eicosapentaenoic acid, EPA, 5Z,8Z,11Z,14Z,17Z-eicosapentaenoic acid, icosapentaenoic acid, timnodonic acid, C20:5 (all cis) acid, C20:5 omega-3, Eicosapentaenoic CID, EPA 5C,8C,11C,14C,17C
Eicosapentaenoic acid (EPA) is an omega-3 fatty acid found primarily in fish oils.
Eicosapentaenoic acid (EPA) is an omega-3 fatty acid that is found in fatty fish.
Eicosapentaenoic Acid is often taken as a supplement in the form of fish oil to improve cardiovascular health and brain health.
Eicosapentaenoic acid (EPA) is an essential omega-3 fatty acid found primarily in cold-water fish like salmon and tuna.
This important nutrient plays several roles in maintaining human health and is often taken as a supplement.
Functional Foods: Eicosapentaenoic Acid is added to fortified foods and beverages to enhance omega-3 content, especially where improved cardiovascular or cognitive nutritional profiles are desired.
Eicosapentaenoic acid (EPA) — CAS 10417-94-4; C₂₀H₃₀O₂ — is a long-chain omega-3 polyunsaturated fatty acid with five cis double bonds and widespread significance in nutrition and physiology.
Eicosapentaenoic Acid is a clear oily liquid at room temperature, biologically active as a precursor to anti-inflammatory and cardiovascular-relevant mediators, and consumed via fish oils, algae, and supplements to support metabolic and heart health.
Eicosapentaenoic Acid is generally safe within normal dietary and supplemental intakes, though attention to oxidation and high-dose interactions is warranted.
Eicosapentaenoic Acid is a 20-carbon long-chain omega-3 polyunsaturated fatty acid, considered essential and must be included in the diet.
Indeed, although mammals have the ability to introduce double bonds at most positions in the fatty acid chain during fat metabolism, they do not have the ability to insert double bonds at the ω-3 and ω-6 positions.
When essential fatty acids are consumed as precursors, they follow a desaturation pathway under the action of delta-6 and delta-5 desaturases until they form the "active" fatty acids: eicosapentaenoic acid (20:5ω-3) (EPA) and docosahexaenoic acid (DHA) (22:6ω-3).
Over the past 100 years, a decrease in omega-3 fatty acid intake, including Eicosapentaenoic Acid, has been observed.
This is especially true for Western diets, characterized by lower consumption of fish and marine foods.
Current intake estimates indicate insufficient consumption according to World Health Organization (WHO) standards.
Most dietary Eicosapentaenoic Acid is consumed in the form of fish or seafood.
Cold-water deep-sea fish, such as salmon, mackerel, halibut and herring, are the most important sources.
Another indirect source of Eicosapentaenoic Acid is the oil of certain plants belonging to the evening primrose and borage families.
These oils contain stearidonic acid, which is metabolized into Eicosapentaenoic Acid in animals and humans.
However, it is not clear whether EPA produced via stearidonic acid metabolism has the same effects as Eicosapentaenoic Acid from other sources.
Essential fatty acids, including Eicosapentaenoic Acid, are crucial for optimal health.
The omega-3 concentration of cell membranes determines the proper functioning of these organs, particularly the heart and the brain.
Eicosapentaenoic Acid should be noted that more than 50% of the brain's mass is made up of lipids, of which more than half are omega-3 fatty acids.
Eicosapentaenoic acid (EPA) is a long-chain omega-3 polyunsaturated fatty acid (PUFA).
It has 20 carbons in its chain compared to the 18 carbons of alpha-linolenic acid (ALA), its precursor omega-3 fatty acid.
Docosahexaenoic acid (DHA) is the other important long-chain omega-3.
Although Eicosapentaenoic Acid can be formed in the body through the conversion of ALA, the conversion rate is very limited meaning that we must have a source in our diet to obtain appropriate amounts.
Eicosapentaenoic acid (EPA) is a long-chain omega-3 polyunsaturated fatty acid found predominantly in oily fish such as salmon, mackerel, and sardines.
Eicosapentaenoic Acid plays a vital role in cardiovascular health, particularly in reducing triglyceride levels and lowering cardiovascular risk when used as prescription-strength icosapent ethyl alongside statin therapy.
Once consumed, Eicosapentaenoic Acid becomes incorporated into cell membranes, where it influences inflammation, cellular signalling, and the production of bioactive compounds.
Available both as dietary supplements and licensed medicines in the UK, Eicosapentaenoic Acid's therapeutic applications extend beyond heart health to include potential benefits in inflammatory conditions and mental health, though evidence varies across these indications.
Eicosapentaenoic acid (EPA) reduces triglyceride levels, lowers cardiovascular risk, and exerts anti-inflammatory effects by incorporating into cell membranes and producing bioactive signalling molecules.
Eicosapentaenoic Acid is a long-chain omega-3 fatty acid found in oily fish that becomes incorporated into cell membranes throughout the body.
Prescription icosapent ethyl (4 g daily) is licensed in the UK for cardiovascular risk reduction in patients with elevated triglycerides on statin therapy.
Eicosapentaenoic Acid produces anti-inflammatory compounds called resolvins and competes with omega-6 fatty acids to reduce pro-inflammatory mediator production.
Common side effects include gastrointestinal symptoms and fishy aftertaste.
High-dose Eicosapentaenoic Acid may increase bleeding risk and atrial fibrillation.
NICE recommends icosapent ethyl for specific cardiovascular indications but does not recommend general omega-3 supplements for cardiovascular disease prevention.
Patients taking anticoagulants or antiplatelet medications require medical supervision when using Eicosapentaenoic Acid due to potential increased bleeding risk.
Eicosapentaenoic Acid is an ω-3 fatty acid and an inhibitor of fatty acid synthase (FASN).
Eicosapentaenoic Acid promotes DNA demethylation in the reexpression of the tumor suppressor gene CCAAT/ enhancer-binding protein δ (C/EBPδ).
Eicosapentaenoic Acid activates the RAS/ERK/C/EBPβ pathway in U937 leukemia cells through demethylation of the CpG island of H-RAS intron 1.
Eicosapentaenoic Acid promotes the relaxation of vascular smooth muscle cells and vasodilation.
Eicosapentaenoic Acid belongs to the class of organic compounds known as long-chain fatty acids.
These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.
Eicosapentaenoic acid (EPA) is not an ordinary fatty acid – it is a crucial nutrient for your health.
Eicosapentaenoic acid (EPA) is a long-chain omega-3 polyunsaturated fatty acid (PUFA) that is biologically important in human nutrition and physiology.
In chemical structure, Eicosapentaenoic Acid is a 20-carbon carboxylic acid with five cis double bonds, with the first double bond located three carbon atoms from the omega (methyl) end of the chain.
As an omega-3 fatty acid, Eicosapentaenoic Acid is found in high concentrations in marine organisms, especially oily fish (e.g., salmon, herring, mackerel, sardines) and certain algae.
In the human body, Eicosapentaenoic Acid acts as a precursor for specific eicosanoids — signaling molecules such as prostaglandin-3, thromboxane-3 and leukotriene-5 — which influence inflammatory responses, platelet function, and cardiovascular health.
Eicosapentaenoic Acid is also widely studied for its potential roles in lowering triglycerides and modulating immune function.
Eicosapentaenoic acid (EPA) is an omega-3 fatty acid that is found along with docosahexaenoic acid (DHA) in cold-water fish, including tuna and salmon.
Eicosapentaenoic Acid prevents the blood from clotting easily, reduces triglyceride levels in the blood, and has effects that might reduce pain and swelling.
Eicosapentaenoic Acid is a US FDA-approved prescription drug for reducing triglyceride levels.
As a supplement, people most commonly use Eicosapentaenoic Acid for heart disease, preventing heart attack, and depression.
Eicosapentaenoic acid (EPA) is an omega−3 fatty acid.
In physiological literature, Eicosapentaenoic Acid is given the name 20:5(n−3).
Eicosapentaenoic Acid also has the trivial name timnodonic acid.
In chemical structure, Eicosapentaenoic Acid is a carboxylic acid with a 20-carbon chain and five cis double bonds.
The first double bond is located at the third carbon from the omega end.
Eicosapentaenoic Acid and DHA ethyl esters (all forms) may be absorbed less well, thus work less well, when taken on an empty stomach or with a low-fat meal.
Eicosapentaenoic Acid is a long-chain fatty acid.
Eicosapentaenoic Acid has been reported in Salpa thompsoni with data available.
Eicosapentaenoic Acid is an essential, polyunsaturated, 20-carbon omega-3 fatty acid with anti-inflammatory and potential antineoplastic and chemopreventive activities.
Eicosapentaenoic Acid may activate caspase 3, resulting in apoptosis in susceptible tumor cell populations.
In addition, Eicosapentaenoic Acid may inhibit cyclooxygenase-2 (COX-2), resulting in inhibition of prostaglandin synthesis and prostaglandin-mediated inflammatory processes.
Eicosapentaenoic Acid is important polyunsaturated fatty acid found in fish oils.
Eicosapentaenoic Acid serves as the precursor for the prostaglandin-3 and thromboxane-3 families.
A diet rich in eicosapentaenoic acid lowers serum lipid concentration, reduces incidence of cardiovascular disorders, prevents platelet aggregation, and inhibits arachidonic acid conversion into the thromboxane-2 and prostaglandin-2 families.
Eicosapentaenoic Acid is an orally active Omega-3 long-chain polyunsaturated fatty acid (ω-3 LC-PUFA).
Eicosapentaenoic Acid exhibits a DNA demethylating action that promotes the re-expression of the tumor suppressor gene CCAAT/enhancer-binding protein δ (C/EBPδ).
Eicosapentaenoic Acid activates RAS/ERK/C/EBPβ pathway through H-Ras intron 1 CpG island demethylation in U937 leukemia cells.
Eicosapentaenoic Acid can promote relaxation of vascular smooth muscle cells and vasodilation.
Eicosapentaenoic Acid is an important polyunsaturated fatty acid found in fish oils.
Eicosapentaenoic Acid serves as the precursor for the prostaglandin-3 and thromboxane-3 families.
A diet rich in eicosapentaenoic acid lowers serum lipid concentration, reduces incidence of cardiovascular disorders, prevents platelet aggregation, and inhibits arachidonic acid conversion into the thromboxane-2 and prostaglandin-2 families.
Eicosapentaenoic acid is an omega-3 fatty acid.
In physiological literature, it is given the name 20:5(n-3).
Eicosapentaenoic Acid's systematic chemical name is all-cis-5,8,11,14,17-icosapentaenoic acid.
Eicosapentaenoic Acid also has the trivial name timnodonic acid.
Chemically, Eicosapentaenoic Acid is a carboxylic acid with a 20-carbon chain and five cis double bonds.
The first double bond is located at the third carbon from the omega end.
Because of the presence of double bonds, EPS is a polyunsaturated fatty acid.
Metabolically Eicosapentaenoic Acid acts as a precursor for prostaglandin-3 (which inhibits platelet aggregation), thromboxane-3, and leukotriene-5 groups.
Eicosapentaenoic Acid is found in fish oils of cod liver, herring, mackerel, salmon, menhaden, and sardine.
Eicosapentaenoic Acid is also found in human breast milk.
USES and APPLICATIONS of EICOSAPENTAENOIC ACID:
Eicosapentaenoic Acid is also used for chemotherapy-related side effects, diabetes, recovery after surgery, and many other purposes, but there is no good scientific evidence to support many of these other uses.
Eicosapentaenoic Acid is widely used to support cardiovascular health by reducing triglyceride levels.
Eicosapentaenoic Acid is a polyunsaturated fatty acid (PUFA) that acts as a precursor for prostaglandin-3 (which inhibits platelet aggregation), thromboxane-3, and leukotriene-5 eicosanoids.
Eicosapentaenoic Acid is both a precursor and the hydrolytic breakdown product of eicosapentaenoyl ethanolamide (EPEA: C22H35NO2; 20:5,n−3).
Although studies of fish oil supplements, which contain both docosahexaenoic acid (DHA) and Eicosapentaenoic Acid, have failed to support claims of preventing heart attacks or strokes, a recent multi-year study of Vascepa (ethyl eicosapentaenoate, the ethyl ester of the free fatty acid), a prescription drug containing only Eicosapentaenoic Acid, was shown to reduce heart attack, stroke, and cardiovascular death by 25% relative to a placebo in those with statin-resistant hypertriglyceridemia.
Eicosapentaenoic Acid helps in lowering blood pressure and improving overall heart function.
Eicosapentaenoic Acid has anti-inflammatory properties that can benefit individuals with rheumatoid arthritis.
Eicosapentaenoic Acid is used as a dietary supplement to support brain health and cognitive function.
Eicosapentaenoic Acid may help in managing symptoms of depression and other mood disorders.
Eicosapentaenoic Acid contributes to the reduction of chronic inflammation in metabolic disorders.
Eicosapentaenoic Acid is often included in formulations for eye health, potentially supporting retinal function.
Eicosapentaenoic Acid is used in combination with docosahexaenoic acid (DHA) for comprehensive omega-3 therapy.
Eicosapentaenoic Acid is applied in medical nutrition therapy for patients with high cardiovascular risk.
Eicosapentaenoic Acid is also investigated for potential benefits in autoimmune diseases and certain cancers.
-Nutrition & Dietary Supplements Use of Eicosapentaenoic Acid:
Eicosapentaenoic Acid is most commonly consumed through fish oil supplements or algae-based omega-3 products.
Eicosapentaenoic Acid is valued for supporting heart health, vascular function, and inflammation balance.
Eicosapentaenoic Acid is often combined with other omega-3s (e.g., DHA) in nutraceutical formulations to achieve broader health effects.
-Clinical & Research Use of Eicosapentaenoic Acid:
Eicosapentaenoic Acid is used in clinical research to explore effects on triglyceride levels, inflammatory markers, and metabolic syndromes.
Pure Eicosapentaenoic Acid standards also serve as analytical and calibration standards in biochemical assays, lipid profiling, and mass spectrometry.
-Biological Pathways uses of Eicosapentaenoic Acid:
In vivo, Eicosapentaenoic Acid participates in biosynthetic cycles of fatty acids, being produced via desaturation and elongation from alpha-linolenic acid (ALA) in marine organisms.
Humans have limited conversion capacity from ALA and therefore depend on dietary sources.
HEALTH BENEFITS AND CLINICAL USES of EICOSAPENTAENOIC ACID:
Eicosapentaenoic Acid exerts multiple physiological effects that contribute to cardiovascular health and metabolic function.
Cardiovascular benefits represent the most extensively researched area, with evidence demonstrating that Eicosapentaenoic Acid can reduce triglyceride levels, a recognised risk factor for cardiovascular disease.
NICE Technology Appraisal 805 specifically recommends icosapent ethyl with statin therapy for reducing cardiovascular risk in adults with established cardiovascular disease, elevated triglycerides (≥1.7 mmol/L), and LDL-cholesterol controlled by statins.
It's important to note that general omega-3 fish oil supplements and other prescription omega-3 products containing both Eicosapentaenoic Acid and DHA are not recommended by NICE for cardiovascular disease prevention.
The anti-inflammatory properties of Eicosapentaenoic Acid have generated interest in various inflammatory conditions.
Eicosapentaenoic Acid competes with arachidonic acid (an omega-6 fatty acid) for incorporation into cell membranes and for metabolism by cyclooxygenase and lipoxygenase enzymes.
This competition results in reduced production of pro-inflammatory mediators.
Some research suggests potential benefits in rheumatoid arthritis, with patients reporting reduced joint pain and stiffness, though evidence quality varies and Eicosapentaenoic Acid should not replace conventional disease-modifying treatments.
UK guidelines do not currently recommend Eicosapentaenoic Acid for rheumatoid arthritis management.
Mental health applications have also been investigated, particularly in depression.
Some studies indicate that Eicosapentaenoic Acid supplementation may provide modest benefits as an adjunct to standard antidepressant therapy.
However, NICE guidelines do not recommend omega-3 supplements as a treatment for depression, and patients should not discontinue prescribed medications without medical supervision.
Other areas of ongoing research include Eicosapentaenoic Acid's potential role in cognitive function, skin health, and inflammatory bowel disease.
Whilst preliminary findings appear promising in some contexts, the evidence base remains insufficient for definitive clinical recommendations.
Patients considering Eicosapentaenoic Acid for conditions beyond established cardiovascular indications should discuss this with their GP or specialist to ensure appropriate, evidence-based management of their condition.
FUNCTION/ USED FOR EICOSAPENTAENOIC ACID:
Eicosapentaenoic Acid has many functions in the body including as a significant component of phospholipid cell membranes in cells throughout the body and providing a rich source of energy.
Eicosapentaenoic Acid is also used to form eicosanoids – signalling molecules used within the cardiovascular, pulmonary, immune and endocrine systems.
Eicosanoids formed from omega-3s such as Eicosapentaenoic Acid are generally more anti-inflammatory than those formed from omega-6s, meaning they could have an anti-inflammatory effect in the body if consumed in greater amounts.
Eicosapentaenoic Acid is considered to be especially important for our heart health by contributing to the normal function of the heart and to normal blood pressure and blood triglyceride levels.
These beneficial effects are obtained with a daily intake of:
3g Eicosapentaenoic Acid + DHA for normal blood pressure.
2g Eicosapentaenoic Acid + DHA for blood triglyceride levels.
250mg Eicosapentaenoic Acid + DHA for normal heart function.
BENEFITS & HEALTH EFFECTS of EICOSAPENTAENOIC ACID:
Eicosapentaenoic Acid is associated with numerous potential health effects:
*Cardiovascular Support:
Regular consumption is linked to lower triglycerides and improved cardiovascular risk profiles.
*Anti-Inflammatory Effects:
As a precursor to specific eicosanoids and lipid mediators, Eicosapentaenoic Acid can modulate inflammatory pathways.
*Platelet Function:
Eicosapentaenoic Acid-derived eicosanoids tend to reduce platelet aggregation, contrasting with the effects of some omega-6 derived counterparts.
*Metabolic Health:
Eicosapentaenoic Acid influences lipid metabolism and may support metabolic balance.
While clinical outcomes vary by context and dose, many studies support Eicosapentaenoic Acid’s beneficial role in population health and chronic disease mitigation when included as part of a balanced omega-3 intake.
CHEMICAL STRUCTURE AND PROPERTIES of EICOSAPENTAENOIC ACID:
Eicosapentaenoic Acid has the chemical formula C20H30O2 with a molecular weight of approximately 302 g/mol.
Eicosapentaenoic Acid’s classified as a polyunsaturated fatty acid (PUFA) with 20 carbon atoms and 5 double bonds in its carbon chain.
The five double bonds are located at positions 5, 8, 11, 14, and 17, which gives Eicosapentaenoic Acid its scientific name of 5,8,11,14,17-eicosapentaenoic acid.
This specific arrangement of double bonds contributes to Eicosapentaenoic Acid’s flexible structure and biological activity.
Eicosapentaenoic Acid exists as a colorless liquid at room temperature and is insoluble in water but soluble in organic solvents.
Eicosapentaenoic Acid oxidizes easily when exposed to air, which is why EPA supplements often contain antioxidants to prevent rancidity.
FUNCTIONAL CHARACTERISTICS & BIOLOGICAL ROLES of EICOSAPENTAENOIC ACID:
Eicosapentaenoic Acid plays several important roles in physiology:
*Biochemical Precursor:
Eicosapentaenoic Acid is converted enzymatically into eicosanoids (prostaglandin-3, thromboxane-3, leukotriene-5 families) that have distinct regulatory effects on inflammation and platelet aggregation compared to eicosanoids derived from omega-6 fatty acids.
*Inflammation and Immunity:
Eicosapentaenoic Acid-derived mediators are generally associated with anti-inflammatory effects and modulation of immune cell signaling.
*Cardiovascular Effects:
Consumption of Eicosapentaenoic Acid is associated with lowering blood triglycerides, potential improvement in vascular function, and reduced risk factors linked to coronary heart disease.
*Membrane Function:
Incorporated into cell membranes, Eicosapentaenoic Acid contributes to membrane fluidity and receptor function in various tissues.
*Mental Health and Development:
While Eicosapentaenoic Acid is biologically active in neural tissue, its roles are often evaluated together with other omega-3s such as DHA.
These roles explain Eicosapentaenoic Acid’s importance in nutrition, health research, dietary supplements, and functional foods.
ALTERNATIVE PARENTS of EICOSAPENTAENOIC ACID:
*Unsaturated fatty acids
*Straight chain fatty acids
*Monocarboxylic acids and derivatives
*Carboxylic acids
*Organic oxides
*Hydrocarbon derivatives
*Carbonyl compounds
SUBSTITUENTS of EICOSAPENTAENOIC ACID:
*Long-chain fatty acid
*Unsaturated fatty acid
*Straight chain fatty acid
*Monocarboxylic acid or derivatives
*Carboxylic acid
*Carboxylic acid derivative
*Organic oxygen compound
*Organic oxide
*Hydrocarbon derivative
*Organooxygen compound
*Carbonyl group
*Aliphatic acyclic compound
EICOSAPENTAENOIC ACID VS. OTHER OMEGA-3S
Eicosapentaenoic Acid is one of three main omega-3 fatty acids important for human health, alongside docosahexaenoic acid (DHA) and alpha-linolenic acid (ALA).
While they’re all omega-3s, they have distinct properties and functions.
Eicosapentaenoic Acid contains 20 carbon atoms with 5 double bonds, while DHA has 22 carbon atoms with 6 double bonds.
ALA is shorter with 18 carbon atoms and 3 double bonds.
Your body can convert some ALA into Eicosapentaenoic Acid and then into DHA, but this conversion is inefficient.
Most health experts recommend getting Eicosapentaenoic Acid and DHA directly from food or supplements.
Eicosapentaenoic Acid and DHA are found primarily in marine sources, while ALA comes mainly from plant sources like flaxseeds, chia seeds, and walnuts.
DIETARY SOURCES of EICOSAPENTAENOIC ACID:
Eicosapentaenoic Acid is available from several dietary sources with varying levels of concentration.
Marine-based sources typically provide the highest amounts, while plant-based alternatives offer indirect pathways to increasing Eicosapentaenoic Acid levels.
*Oily Fish and Seafood
Oily fish represent the most concentrated natural sources of Eicosapentaenoic Acid.
Salmon contains approximately 590 mg of Eicosapentaenoic Acid per 3-ounce serving, making it one of the richest dietary sources available to you.
Mackerel provides even higher amounts, with up to 800 mg per serving, while herring offers around 700 mg.
Sardines pack impressive Eicosapentaenoic Acid content despite their small size, delivering about 400 mg per 3-ounce serving.
These tiny fish are convenient as they’re often available canned.
Tuna varies in Eicosapentaenoic Acid content depending on the species.
Bluefin tuna contains more Eicosapentaenoic Acid than yellowfin or skipjack varieties.
Fresh cod provides modest amounts of Eicosapentaenoic Acid (around 100 mg per serving), though less than fattier fish species.
Shellfish, like oysters and mussels, also contain appreciable amounts of Eicosapentaenoic Acid, though they are generally lower than oily fish.
USES & EFFECTIVENESS of EICOSAPENTAENOIC ACID:
Effective for
High levels of fats called triglycerides in the blood (hypertriglyceridemia).
Taking a prescription drug containing Eicosapentaenoic Acid by mouth lowers triglycerides levels by 33% in people with very high levels.
It's not clear if taking Eicosapentaenoic Acid supplements has the same effect.
Possibly Effective for
*Heart disease.
Taking a prescription drug containing Eicosapentaenoic Acid by mouth along with statin drugs reduces complications such as heart attack and stroke in people with heart disease.
It's not clear if taking Eicosapentaenoic Acid supplements helps.
*Depression.
Taking pure Eicosapentaenoic Acid or fish oil containing at least 60% EPA by mouth reduces symptoms of depression in some people.
Eicosapentaenoic Acid might work best when used along with antidepressant drugs.
*Migraine.
Taking Eicosapentaenoic Acid by mouth may reduce how many migraines some people get each month.
It's not clear if taking Eicosapentaenoic Acid can help to make migraines less severe.
*Heart attack.
Taking a prescription drug containing Eicosapentaenoic Acid by mouth along with statin drugs reduces the risk for heart attack in people at risk for heart disease.
Taking Eicosapentaenoic Acid supplements by mouth also seems to help.
There is interest in using Eicosapentaenoic Acid for a number of other purposes, but there isn't enough reliable information to say whether it might be helpful.
SOURCES of EICOSAPENTAENOIC ACID:
Eicosapentaenoic Acid is obtained in the human diet by eating oily fish, e.g., cod liver, herring, mackerel, salmon, menhaden and sardine, various types of edible algae, or by taking supplemental forms of fish oil or algae oil.
Eicosapentaenoic Acid is also found in human breast milk.
Fish, like most vertebrates, can synthesize very little Eicosapentaenoic Acid from dietary alpha-linolenic acid (ALA).
Because of this extremely low conversion rate, fish primarily obtain Eicosapentaenoic Acid from the algae they consume.
Eicosapentaenoic Acid is available to humans from some non-animal sources (e.g., commercially, from Yarrowia lipolytica, and from microalgae such as Nannochloropsis oculata, Monodus subterraneus, Chlorella minutissima and Phaeodactylum tricornutum, which are being developed as a commercial source).
Eicosapentaenoic Acid is not usually found in higher plants, but it has been reported in trace amounts in purslane.
In 2013, it was reported that a genetically modified form of the plant camelina produced significant amounts of Eicosapentaenoic Acid.
The human body converts a portion of absorbed alpha-linolenic acid (ALA) to Eicosapentaenoic Acid.
ALA is itself an essential fatty acid, and humans need an appropriate supply of it.
The efficiency of the conversion of ALA to Eicosapentaenoic Acid, however, is much lower than the absorption of EPA from food containing it.
Because Eicosapentaenoic Acid is also a precursor to docosahexaenoic acid (DHA), ensuring a sufficient level of EPA on a diet containing neither EPA nor DHA is harder both because of the extra metabolic work required to synthesize EPA and because of the use of Eicosapentaenoic Acid to metabolize into DHA.
Medical conditions like diabetes or certain allergies may significantly limit the human body's capacity for metabolization of Eicosapentaenoic Acid from ALA.
FORMS of EICOSAPENTAENOIC ACID:
Commercially available dietary supplements are most often derived from fish oil and are typically delivered in the triglyceride, ethyl ester, or phospholipid form of Eicosapentaenoic Acid.
There is debate among supplement manufacturers about the relative advantages and disadvantages of the different forms.
One form found naturally in algae, the polar lipid form, has been shown to have improved bioavailability over the ethyl ester or triglyceride form.
Similarly, DHA or Eicosapentaenoic Acid in the lysophosphatidylcholine (LPC) form was found to be more efficient than triglyceride and phosphatidylcholines (PC) in a 2020 study.
BIOSYNTHESIS of EICOSAPENTAENOIC ACID:
***Aerobic eukaryote pathway
Aerobic eukaryotes, specifically microalgae, mosses, fungi, and most animals (including humans), perform biosynthesis of Eicosapentaenoic Acid usually as a series of desaturation and elongation reactions, catalyzed by the sequential action of desaturase and elongase enzymes.
This pathway, originally identified in Thraustochytrium, applies to these groups:
*a desaturation at the sixth carbon of alpha-linolenic acid by a Δ6 desaturase to produce stearidonic acid (SDA, 18:4 ω-3).
*elongation of the stearidonic acid by a Δ6 elongase to produce eicosatetraenoic acid (ETA, 20:4 ω-3).
*desaturation at the fifth carbon of eicosatetraenoic acid by a Δ5 desaturase to produce eicosapentaenoic acid (EPA, 20:5 ω-3).
***Polyketide synthase pathway
Marine bacteria and the microalgae Schizochytrium use an anerobic polyketide synthase (PKS) pathway to synthesize DHA.
The PKS pathway includes six enzymes namely, 3-ketoacyl synthase (KS), 2 ketoacyl-ACP-reductase (KR), dehydrase (DH), enoyl reductase (ER), dehydratase/2-trans 3-cos isomerase (DH/2,3I), dehydratase/2-trans, and 2-cis isomerase (DH/2,2I).
The biosynthesis of Eicosapentaenoic Acid varies in marine species, but most of the marine species' ability to convert C18 PUFA to LC-PUFA is dependent on the fatty acyl desaturase and elongase enzymes.
The molecule basis of the enzymes will dictate where the double bond is formed on the resulting molecule.
The proposed polyketide synthesis pathway of Eicosapentaenoic Acid in Shewanella (a marine bacterium) is a repetitive reaction of reduction, dehydration, and condensation that uses acetyl-CoA and malonyl-CoA as building blocks.
The mechanism of α-linolenic acid to Eicosapentaenoic Acid involves the condensation of malonyl-CoA to the pre-existing α-linolenic acid by KS.
The resulting structure is converted by NADPH dependent reductase, KR, to form an intermediate that is dehydrated by the DH enzyme.
The final step is the NADPH-dependent reduction of a double bond in trans-2-enoyl-ACP via ER enzyme activity.
The process is repeated to form Eicosapentaenoic Acid.
CLINICAL SIGNIFICANCE of EICOSAPENTAENOIC ACID:
The US National Institute of Health's MedlinePlus lists medical conditions for which Eicosapentaenoic Acid (alone or in concert with other ω-3 sources) is known or thought to be an effective treatment.
Most of these involve its ability to lower inflammation.
Intake of large doses (2.0 to 4.0 g/day) of long-chain omega−3 fatty acids as prescription drugs or dietary supplements are generally required to achieve significant (> 15%) lowering of triglycerides, and at those doses the effects can be significant (from 20% to 35% and even up to 45% in individuals with levels greater than 500 mg/dL).
Dietary supplements containing Eicosapentaenoic Acid and DHA lower triglycerides in a dose dependent manner.
However, DHA appears to raise low-density lipoprotein (the variant which drives atherosclerosis, sometimes inaccurately called "bad cholesterol") and LDL-C values (a measurement/estimate of the cholesterol mass within LDL-particles), while Eicosapentaenoic Acid does not.
This effect has been seen in several meta-analyses that combined hundreds of individual clinical trials in which both Eicosapentaenoic Acid and DHA were part of a high dose omega−3 supplement, but it is when Eicosapentaenoic Acid and DHA are given separately that the difference can be seen clearly.
Ordinary consumers commonly obtain Eicosapentaenoic Acid and DHA from foods such as fatty fish, fish oil dietary supplements, and less commonly from algae oil supplements in which the omega−3 doses are lower than those in clinical experiments.
Omega−3 fatty acids, particularly Eicosapentaenoic Acid, have been studied for their effect on autistic spectrum disorder (ASD).
Some have theorized that, since omega−3 fatty acid levels may be low in children with autism, supplementation might lead to an improvement in symptoms.
Well-controlled studies have shown no statistically significant improvement in symptoms as a result of high-dose omega−3 supplementation.
In addition, studies have shown that omega−3 fatty acids may be useful for treating depression.
THE POWER of EICOSAPENTAENOIC ACID:
Eicosapentaenoic Acid is a polyunsaturated omega-3 fatty acid.
In simple terms, it belongs to the healthy fats and it has a whole range of positive effects on your health.
One of the most remarkable is its ability, to reduce inflammation in the body.
Inflammations are involved in the development of many chronic diseases, from heart disease to arthritis to cancer.
Eicosapentaenoic Acid can inhibit these inflammatory processes and help reduce your risk for these diseases.
Furthermore, Eicosapentaenoic Acid plays an important role in the maintenance of heart health.
Eicosapentaenoic Acid helps regulate blood pressure, lower triglyceride levels in the blood, and improve blood clotting.
All these factors contribute to reducing the risk of cardiovascular diseases and keeping your heart strong and healthy.
In our guide on blood lipid levels we provide you with a deeper insight into the health effects of the individual markers.
WHERE CAN I FIND EICOSAPENTAENOIC ACID?
The best source of Eicosapentaenoic Acid is fatty fish such as salmon, mackerel, sardines, and herring.
If you're not a fan of fish, don't worry – there are also plant-based sources of Eicosapentaenoic Acid.
Algal oil supplements are a great option for vegetarians and vegans to ensure they get enough of this important fatty acid.
EICOSAPENTAENOIC ACID VS. DHA: WHAT IS THE DIFFERENCE?
Eicosapentaenoic acid (Eicosapentaenoic Acid) and Docosahexaenoic acid (DHA) are two important omega-3 fatty acids that play a crucial role in your health.
Structurally, they are very similar, but they differ in their biological function and health effects.
Eicosapentaenoic Acid is known for its anti-inflammatory properties and its role in supporting heart health.
DHA, on the other hand, is particularly important for brain and eye health and plays a crucial role in the neurological development of infants.
EICOSAPENTAENOIC ACID AND ALA: WHAT IS THE DIFFERENCE HERE?
Alpha-linolenic acid (ALA) is also an omega-3 fatty acid, but here too we find some differences compared to eicosapentaenoic acid.
As mentioned, Eicosapentaenoic Acid is mainly found in fatty fish such as salmon, mackerel, and sardines, while ALA is found in plant foods such as flaxseeds, walnuts, and chia seeds.
The body can use eicosapentaenoic acid directly, while ALA must first be converted into Eicosapentaenoic Acid and then into docosahexaenoic acid (DHA) to gain its full health benefits.
PHYSICAL and CHEMICAL PROPERTIES of EICOSAPENTAENOIC ACID:
Chemical formula: C20H30O2
Molar mass: 302.451 g/mol
Average Molecular Weight: 302.451
Monoisotopic Molecular Weight: 302.224580204
IUPAC Name: (5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoic acid
Traditional Name: eicosapentaenoic acid
CAS Registry Number: 10417-94-4
SMILES: CCC=C/CC=C/CC=C/CC=C/CC=C/CCCC(O)=O
InChI Identifier: InChI=1S/C20H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h3-4,6-7,9-10,12-13,15-16H,2,5,8,11,14,17-19H2,1H3,(H,21,22)/b4-3-,7-6-,10-9-,13-12-,16-15-
InChI Key: JAZBEHYOTPTENJ-JLNKQSITSA-N
Molecular Weight: 302.5 g/mol
XLogP3-AA: 5.6
Hydrogen Bond Donor Count: 1
Hydrogen Bond Acceptor Count: 2
Rotatable Bond Count: 13
Exact Mass: 302.224580195 Da
Monoisotopic Mass: 302.224580195 Da
Topological Polar Surface Area: 37.3 Ų
Heavy Atom Count: 22
Formal Charge: 0
Complexity: 398
Isotope Atom Count: 0
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 5
Undefined Bond Stereocenter Count: 0
Covalently-Bonded Unit Count: 1
Compound Is Canonicalized: Yes
Preferred Name: Eicosapentaenoic acid (EPA)
Molecular Formula: C20H30O2
Molecular Weight: 302.45 g/mol
CAS Number: 10417-94-4
EC / EINECS Number: not always listed in standard chemical inventories for pure nutrient compounds
PubChem CID: 446284
ChemSpider ID: 393682
IUPAC Name: (5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoic acid
Lipid Classification: Omega-3 (n-3) fatty acid; shorthand nomenclature 20:5(n-3)
Appearance: Clear, colorless to pale yellow oily liquid at room temperature
State: Liquid (oil)
Molecular Formula: C20H30O2
Molecular Weight: 302.45 g/mol
Density: 0.94 g/cm³ at 25 °C
Melting Point: –54 to –53 °C
Boiling Point: 439 °C
Refractive Index: 1.4977–1.4986
Flash Point: 93–100 °C
Water Solubility: Practically insoluble in water; soluble in organic solvents such as methanol, ethanol, DMSO, DMF, and oils
pKa: 4.75
Stability: Highly unsaturated structure makes EPA sensitive to oxidation (heat, light and air can promote lipid peroxidation)
Partition Coefficient: High (lipophilic)
Vapour Pressure: Very low
FIRST AID MEASURES of EICOSAPENTAENOIC ACID:
-Description of first-aid measures
*General advice:
Show this material safety data sheet to the doctor in attendance.
*If inhaled:
After inhalation:
Fresh air.
*In case of skin contact:
Take off immediately all contaminated clothing.
Rinse skin with
water/ shower.
*In case of eye contact:
After eye contact:
Rinse out with plenty of water.
Call in ophthalmologist.
Remove contact lenses.
*If swallowed:
After swallowing:
Immediately make victim drink water (two glasses at most).
Consult a physician.
-Indication of any immediate medical attention and special treatment needed.
No data available
ACCIDENTAL RELEASE MEASURES of EICOSAPENTAENOIC ACID:
-Environmental precautions:
Do not let product enter drains.
-Methods and materials for containment and cleaning up:
Cover drains.
Collect, bind, and pump off spills.
Observe possible material restrictions.
Take up dry.
Dispose of properly.
Clean up affected area.
FIRE FIGHTING MEASURES of EICOSAPENTAENOIC ACID:
-Extinguishing media:
*Suitable extinguishing media:
Carbon dioxide (CO2)
Foam
Dry powder
*Unsuitable extinguishing media:
For this substance/mixture no limitations of extinguishing agents are given.
-Further information:
Prevent fire extinguishing water from contaminating surface water or the ground water system.
EXPOSURE CONTROLS/PERSONAL PROTECTION of EICOSAPENTAENOIC ACID:
-Control parameters:
--Ingredients with workplace control parameters:
-Exposure controls:
--Personal protective equipment:
*Eye/face protection:
Use equipment for eye protection.
Safety glasses
*Body Protection:
protective clothing
*Respiratory protection:
Recommended Filter type: Filter A
-Control of environmental exposure:
Do not let product enter drains.
HANDLING and STORAGE of EICOSAPENTAENOIC ACID:
-Conditions for safe storage, including any incompatibilities:
*Storage conditions:
Tightly closed.
Dry.
STABILITY and REACTIVITY of EICOSAPENTAENOIC ACID:
-Chemical stability:
The product is chemically stable under standard ambient conditions (room temperature).
-Possibility of hazardous reactions:
No data available
