Eicosapentaenoic acid

Eicosapentaenoic acid

Names
IUPAC name (5Z,8Z,11Z,14Z,17Z)-5,8,11,14,17-icosapentaenoic acid
Identifiers
CAS Number	10417-94-4 Y
3D model (Jmol)	Interactive image
ChEBI	CHEBI:28364 Y
ChEMBL	ChEMBL460026 Y
ChemSpider	393682 Y
DrugBank	DB00159 Y
ECHA InfoCard	100.117.069
IUPHAR/BPS	3362
UNII	AAN7QOV9EA Y
InChI 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- Y Key: JAZBEHYOTPTENJ-JLNKQSITSA-N Y InChI=1/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- Key: JAZBEHYOTPTENJ-JLNKQSITBZ
SMILES O=C(O)CCC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC
Properties
Chemical formula	C20H30O2
Molar mass	302.451 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y  (what is YN ?)
Infobox references

Eicosapentaenoic acid (EPA; also icosapentaenoic acid) is an omega-3 fatty acid. In physiological literature, it is given the name 20:5(n-3). It also has the trivial name timnodonic acid. In chemical structure, EPA 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.

EPA is a polyunsaturated fatty acid (PUFA) that acts as a precursor for prostaglandin-3 (which inhibits platelet aggregation), thromboxane-3, and leukotriene-5 eicosanoids. Studies of fish oil supplements, which contain EPA, have failed to support claims of preventing heart attacks or strokes.

It 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 seaweed and phytoplankton. It is also found in human breast milk.

However, fish can either synthesize EPA from fatty acids precursors found in their alimentation or obtain it from the algae they consume. It is available to humans from some non-animal sources (e.g. commercially, from microalgae, which are being developed as a commercial source). EPA 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.