PRODUCTS

EICOSAPENTAENOIC ACID

CAS NUMBER: 10417-94-4

UNII NUMBER: AAN7QOV9EA

MOLECULAR FORMULA: C20H30O2

MOLECULAR WEIGHT: 302.5

IUPAC NAME: (5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoic acid

Eicosapentaenoic Acid (EPA; also icosapentaenoic acid) 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 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 EPA, was shown to reduce heart attack, stroke, and cardiovascular death by 25% relative to a placebo in those with statin-resistant hypertriglyceridemia.

Forms:
Triglyceride is the natural form.
Basically, all supplements sold at present are in triglyceride form and some in ethyl ester and phospholipid form.
However, some bioavailability of DHA or Eicosapentaenoic Acid in the lysophosphatidylcholine (LPC) form is more efficient than triglyceride and phosphatidylcholines (PC) according to a 2020 study.

Sources:
Eicosapentaenoic Acid is obtained in the human diet by eating oily fish or fish oil, e.g., cod liver, herring, mackerel, salmon, menhaden and sardine and various types of edible algae.
Eicosapentaenoic Acid is also found in human breast milk.

Fish can synthesize Eicosapentaenoic Acid from fatty acids found in their alimentation or obtain it 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 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 EPA.

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 Eicosapentaenoic Acid.

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 EPA to metabolize into DHA. Medical conditions like diabetes or certain allergies may significantly limit the human body's capacity for metabolization of EPA from ALA.

Biosynthesis of Eicosapentaenoic Acid:
The biosynthesis of Eicosapentaenoic Acid (EPA) in prokaryotes and eukaryotes involves polyketide synthase (PKS).
The polyketide 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.

Here is an overview of the possible biosynthesis pathways of Eicosapentaenoic Acid from fatty acid synthesis (FAS).
The reactions are mediated by desaturases enzymes with Δx specificity and elongated by elongases of fatty acid chains.

The proposed polyketide synthesis pathway of Eicosapentaenoic Acid in Shewanella 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-enoly-ACP via ER enzyme activity.
The process is repeated to form Eicosapentaenoic Acid.

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 one of several omega-3 fatty acids.
Eicosapentaenoic Acid is found in cold-water fatty fish, such as salmon.
Eicosapentaenoic Acid is also found in fish oil supplements, along with docosahexaenoic acid (DHA).

Eicosapentaenoic Acids are part of a healthy diet that helps lower risk of heart disease.
Getting more Eicosapentaenoic Acid in your diet has positive effects on coronary heart disease, high triglycerides (fats in the blood), high blood pressure, and inflammation.

USES:
Attention-Deficit Hyperactivity Disorder (ADHD):
Because children need omega-3 fatty acids for their brains to develop properly, researchers have looked at whether fish oil might reduce ADHD symptoms.
So far, results have been mixed. One study showed fish oil might help, but many people dropped out of the study before it was done.

Depression:
Some studies show that fish oil reduces symptoms of depression.
Other studies suggest it may be a kind of Eicosapentaenoic Acid known as ethyl-EPA (and not DHA) that reduces symptoms.

Heart Disease:
Eicosapentaenoic Acid seems to help people who already have heart disease.
Eicosapentaenoic Acid also may lower the risk for developing heart disease.
Eicosapentaenoic Acids found in fish oil help lower triglycerides and blood pressure, reduce the risk of blood clots, improve the health of arteries and reduce the amount of arterial plaque, which narrows arteries, and causes heart disease.

Rheumatoid Arthritis:
Several small studies indicate that fish oil may help reduce symptoms and inflammation from rheumatoid arthritis.
However, Eicosapentaenoic Acid does not stop joint damage from getting worse.

Menopause:
One study found that Eicosapentaenoic Acid reduced the number of hot flashes by 1.58 per day in menopausal women.
Eicosapentaenoic Acid did not decrease the severity of the hot flashes, however.

Menstrual Pain:
Eicosapentaenoic Acid appears to reduce the pain of menstrual cramps when taken on a regular basis (not just when menstruating).

Raynaud Syndrome:
Several studies show that high doses (12 g) of fish oil can make fingers and toes less sensitive to cold when people have Raynaud syndrome.
Doses this high should be taken only under a doctor's supervision.

Lupus:
Two small studies suggested that fish oil reduced fatigue and joint pain from lupus.

Other Conditions:
Omega-3 fatty acids, including EPA, may also have positive effects on:
-lung and kidney diseases
-type 2 diabetes
-obesity
-ulcerative colitis
-Crohn disease
-anorexia nervosa
-burns
-osteoarthritis
-osteoporosis
-early stages of colorectal cancer

Dietary Sources:
Eicosapentaenoic Acid is found in:
-cold-water fatty fish
-including salmon
-tuna
-mackerel
-sardines
-shellfish
-herring

Although some of these fish contain low levels of mercury, according to the Food and Drug Administration (FDA) eating several servings of fish each week poses no risk to healthy people and offers many health benefits.
Women who are pregnant or planning to become pregnant should avoid Atlantic mackerel, shark, swordfish, and tilefish, and eat less than 6 oz. of white albacore tuna per week.
These fish tend to be higher in mercury.

High-quality fish oil supplements made by manufacturers who test for mercury and other toxins do not have the same risk of mercury contamination.
Read labels carefully and check for purity, or ask your doctor to help you find the best quality fish oil supplement.

Eicosapentaenoic Acid is a fatty acid found in the flesh of cold-water fish, including mackerel, herring, tuna, halibut, salmon, cod liver, whale blubber, or seal blubber.
Eicosapentaenoic Acid is taken by mouth for some heart-related conditions including clogged heart arteries (coronary artery disease), to prevent or treat heart attacks, and to reduce levels of blood fats called triglycerides in people with very high levels.
Eicosapentaenoic Acid is also used for some mental conditions including schizophrenia, personality disorder.

Eicosapentaenoic Acid is an omega-3 fatty acid C20H30O2 found especially in fish oils.
Eicosapentaenoic Acid (EPA) or timnodonic acid is a polyunsaturated fatty acid found in fish oil with antihyperlipidemic, antihyperglycemic, antiinflammatory, and antioxidant properties.

Eicosapentaenoic Acid is An essential, polyunsaturated, 20-carbon omega-3 fatty acid with anti-inflammatory and potential antineoplastic and chemopreventive activities.
Eicosapentaenoic Acid (EPA) may activate caspase 3, resulting in apoptosis in susceptible tumor cell populations.
In addition, this agent may inhibit cyclooxygenase-2, resulting in inhibition of prostaglandin synthesis and prostaglandin-mediated inflammatory processes.

Eicosapentaenoic Acid is an omega-3 fatty acid that can reduce symptoms of depression and help fight inflammation in our body.
Eicosapentaenoic Acid (EPA) is one of several omega-3 fatty acids.

Eicosapentaenoic Acid is found in cold-water fatty fish, such as salmon. It is also found in fish oil supplements, along with docosahexaenoic acid (DHA).
Eicosapentaenoic Acid is a type of n-3 polyunsaturated fatty acids.
Eicosapentaenoic Acid (EPA or also icosapentaenoic acid) 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 is obtained in the human diet by eating oily fish or fish oil—cod liver, herring, mackerel, salmon, menhaden and sardine.

PHYSICAL PROPERTIES:

-Molecular Weight: 302.5

-XLogP3-AA: 5.6

-Exact Mass: 302.224580195

-Monoisotopic Mass: 302.224580195

-Topological Polar Surface Area: 37.3 Å²

-Physical Description: Liquid

-LogP: 6.1

-Collision Cross Section: 178.53 Å²

-Melting point: −53 °C

-Boiling point: 439℃

-Density: 0.943 g/mL at 25 °C(lit.)

-Refractive index: n20/D 1.4977(lit.)

-Flash Point: 93 °C

-Storage temperature: -20°C

-Solubility: Soluble in methanol

-pka: 4.75±0.10(Predicted)

-Form: liquid

-Sensitive: Air & Light Sensitive

Eicosapentaenoic Acid is also found in human breast milk.
Eicosapentaenoic Acid is available from some non-animal sources—spirulina and microalgae.

Microalgae 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.

Eicosapentaenoic Acid (FFA) form of eicosapentaenoic acid (EPA), a polyunsaturated long-chain fatty acid found in fish oil with a 20-carbon backbone and 5 double bonds, with potential supplementing, anti-inflammatory, anti-thrombotic, immunomodulating, anti-angiogenic and chemopreventive activities.
Upon administration of icosapent, the free form of Eicosapentaenoic Acid is incorporated in cell membrane phospholipids and replaces arachidonic acid.
This inhibits arachidonic acid conversion into thromboxanes and prostaglandin E2 (PGE2).

Upon oral administration of icosapent, the Eicosapentaenoic Acid-FFA prevents and suppresses colonic neoplasia and reduces polyp formation and growth through as of yet not fully elucidated mechanisms.
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 a natural product found in Grimmia pilifera, Plagiothecium euryphyllum, and other organisms with data available.

CHEMICAL PROPERTIES:

-Hydrogen Bond Donor Count: 1

-Hydrogen Bond Acceptor Count: 2

-Rotatable Bond Count: 13

-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

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 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).
Eicosapentaenoic Acid is a fatty acid found in the flesh of cold-water fish, including mackerel, herring, tuna, halibut, salmon, cod liver, whale blubber, or seal blubber.

Eicosapentaenoic Acid is taken by mouth for some heart-related conditions including clogged heart arteries (coronary artery disease), to prevent or treat heart attacks, and to reduce levels of blood fats called triglycerides in people with very high levels.
Eicosapentaenoic Acid is also used for some mental conditions including schizophrenia, personality disorder.

SYNONYMS:

Eicosapentaenoic acid
Timnodonic acid
Icosapent
Icosapentaenoic acid
cis-5,8,11,14,17-Eicosapentaenoic acid
5,8,11,14,17-EICOSAPENTAENOIC ACID
(5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoic acid
Icosapento
Icosapentum
5Z,8Z,11Z,14Z,17Z-Eicosapentaenoic acid
(all-Z)-5,8,11,14,17-Eicosapentaenoic acid
(5Z,8Z,11Z,14Z,17Z)-5,8,11,14,17-eicosapentaenoic acid
Icosapent
(5Z,8Z,11Z,14Z,17Z)-Eicosapentaenoic acid
5,8,11,14,17-Icosapentaenoic acid
(5Z,8Z,11Z,14Z,17Z)-Icosapentaenoic acid
Omega-3-Carboxylic Acids
(5Z,8Z,11Z,14Z,17Z)-Eicosapentaenoate
all-cis-icosa-5,8,11,14,17-pentaenoic acid
Icosapent (INN)
cis-Delta(5,8,11,14,17)-eicosapentaenoic acid
5,8,11,14,17-Eicosapentaenoic acid, (all-Z)-
Icosapentaenoate
(all-Z)-delta5,8,11,14,17-Eicosapentaenoic acid
C20:5n-3,6,9,12,15
eicosapentaenoate
cis-5,8,11,14,17-EPA
EICOSAPENTAENOIC ACID (20:5 n-3)
all-cis-5,8,11,14,17-icosapentaenoic acid
all-cis-5,8,11,14,17-eicosapentaenoic acid
all cis-5,8,11,14,17-Eicosapentaenoic Acid
Miraxion
Eicosapentanoic acid
Eye Q
Eye-Q
5,8,11,14,17-Eicosapentaenoic acid, (5Z,8Z,11Z,14Z,17Z)-
EPA
Icosapentum
C20:5 omega-3
Icosapento ]
(5Z,8Z,11Z,14Z,17Z)-icosapentaenoate
Timnodonate
all-cis-icosapentaenoate
all-cis-icosapentaenoic acid
5,8,11,14,17-Icosapentaenoate
5,8,11,14,17-Eicosapentaenoate
cis-5,8,11,14,17-eicosapentaenoate
5Z,8Z,11Z,14Z,17Z-Eicosapentaenoate
5,8,11,14,17-Eicosapentaenoic acid (6CI)
all cis-5,8,11,14,17-Icosapentaenoic Acid
(all-cis)-5,8,11,14,17-Eicosapentaenoic acid
z,z,z,z,z-eicosa-5,8,11,14,17-pentaenoic acid
(Z,Z,Z,Z,Z)-5,8,11,14,17-eicosapentaenoic acid
BRD-K47192521-001-02-1
cis-5,8,11,14,17-Eicosapentaenoic acid, >=99%
7F8BF016-B146-4F72-A52E-B9298BA3A9AB
C20H30O2 (cis-5,8,11,14,17-eicosapentaenoic acid)
Eicosapentaenoic acid, 5,8,11,14,17-(Z,Z,Z,Z,Z)-
5,8,11,14,17-Eicosapentaenoic acid, (all-Z)- (8CI)
cis-5,8,11,14,17-Eicosapentaenoic acid, >=85%, liquid
cis-5,8,11,14,17-Eicosapentaenoic acid, analytical standard
Eicosa-5Z,8Z,11Z,14Z,17Z-pentaenoic Acid (20:5, n-3)
(5Z,8Z,11 Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoic acid
(5Z,8Z,11Z,14Z,17Z)-eicosa-5,8,11,14,17-pentaenoic acid
cis, cis, cis, cis, cis-eicosa-5,8,11,14,17-pentaenoic acid
5,8,11,14,17-Eicosapentaenoic acid, (5Z,8Z,11Z,14Z,17Z)- (9CI)
cis-5,8,11,14,17-Eicosapentaenoic acid