| Eicosapentaenoic acid | |
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(5Z,8Z,11Z,14Z,17Z)-eicosa- |
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| Identifiers | |
| CAS number | 10417-94-4 |
| ChemSpider | 393682 |
| UNII | AAN7QOV9EA |
| DrugBank | DB00159 |
| ChEBI | CHEBI:28364 |
| ChEMBL | CHEMBL460026 |
| Jmol-3D images | Image 1 |
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| Properties | |
| Molecular formula | C20H30O2 |
| Molar mass | 302.451 g/mol |
| (verify) (what is: /?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
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| Infobox references | |
Eicosapentaenoic acid (EPA or 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 groups (all eicosanoids).
It is obtained in the human diet by eating oily fish or fish oil— e.g., cod liver, herring, mackerel, salmon, menhaden and sardine. It is also found in human breast milk.
However, fish do not naturally produce EPA, but obtain it from the algae they consume.[1] It is available to humans from some non-animal sources (e.g., commercially, from microalgae). Microalgae are being developed as a commercial source.[2] EPA is not usually found in higher plants, but it has been reported in trace amounts in purslane.[3] Microalgae, and supplements derived from it, are excellent alternative sources of EPA and other fatty acids, since fish often contain toxins due to pollution.[1]
The human body can (and in case of a purely vegetarian diet often must, unless the aforementioned algae or supplements derived from them are consumed) also convert alpha-linolenic acid (ALA) to EPA, but this is much less efficient than the resorption of EPA from food containing it, and ALA is itself an essential fatty acid, an appropriate supply of which must be ensured. Because EPA 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 DHA. Medical conditions like diabetes or certain allergies may significantly limit the human body's capacity for metabolization of EPA from ALA.[4]
The US National Institute of Health's MedlinePlus lists medical conditions for which EPA (alone or in concert with other ω-3 sources) is known or thought to be an effective treatment.[5] Most of these involve its ability to lower inflammation.
Among omega-3 fatty acids, it is thought that EPA in particular may possess some beneficial potential in mental conditions, such as schizophrenia.[6][7] Several studies report an additional reduction in scores on symptom scales used to assess the severity of symptoms, when additional EPA is taken.
Studies published around 2004 have suggested that EPA may decrease depression and, importantly, suicidal behavior. One such study,[8] took blood samples of 100 suicide attempt patients and compared the blood samples to those of controls and found that levels of eicosapentaenoic acid were significantly lower in the washed red blood cells of the suicide-attempt patients. A 2009 metastudy found that patients taking omega-3 supplements with a higher EPA:DHA ratio experienced less depressive symptoms. [9]
EPA has inhibitory effect on CYP2C9 and CYP2C19 hepatic enzymes. At high dose, it may also inhibit the activity of CYP2D6 and CYP3A4, important enzymes involved in drug metabolism.[10]
Research suggests that EPA improves the response of patients to chemotherapy, possibly by modulating the production of eicosanoid.[11]
In a study published in 2011, EPA was shown to be significantly more effective than placebo for treating hyperactivity and attention symptoms, both together and separately.[12]
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