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Eicosapentaenoic acid
| Eicosapentaenoic acid | |
|---|---|
 |
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| IUPAC name | (5Z,8Z,11Z,14Z,17Z)-icosa- 5,8,11,14,17-pentaenoic acid |
| Identifiers | |
| CAS number | |
| SMILES | CCC=CCC=CCC=CCC=CCC=CCCCC(=O)O |
| Properties | |
| Molecular formula | C20H30O2 |
| Molar mass | 302.451 g/mol |
|
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references |
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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. Chemically, 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 and its metabolites act in the body largely by their interactions with the metabolites of arachidonic acid; see Essential fatty acid interactions for detail.
EPA is a polyunsaturated fatty acid that acts as a precursor for prostaglandin-3 (which inhibits platelet aggregation), thromboxane-3 and leukotriene-5 groups (all eicosanoids).
Sources
It is obtained in the human diet by eating oily fish or fish oil—cod liver, herring, mackerel, salmon, menhaden and sardine. It is also found in human breast milk.
It is available from some non-animal sources—spirulina and microalgae. Microalgae are being deveolped as a commercial source.[1] EPA is not usually found in higher plants, but it has been reported in trace amounts in purslane.[2]
Clinical significance
The US National Institute of Health's MedlinePlus lists a large number of conditions in which EPA (alone or in concert with other ω-3 sources) is known or thought to be effective.[3] Most of these involve its ability to lower inflammation.
Among omega-3 fatty acids, in particular EPA is thought to possess beneficial potential in mental conditions, such as schizophrenia. Its effect is optimal at doses of 1-2 gram daily as add-on therapy to antipsychotics. Several studies report an additional reduction in scores on symptom scales used to assess the severity of symptoms, when additional EPA is taken. In the acute phase of the disease, fewer people may need antipsychotics within a certain period or some may need lower doses.
See also
- Chlorella
- Cyanobacteria
- Docosahexaenoic acid
- List of omega-3 fatty acids
- Polyunsaturated fatty acids
- Snake oil
References
- ^ Jess Halliday (12/01/2007). Water 4 to introduce algae DHA/EPA as food ingredient. Retrieved on 2007-02-09.
- ^ Simopoulos, Artemis P (2002). "Omega-3 fatty acids in wild plants, nuts and seeds". Asia Pacific Journal of Clinical Nutrition 11 (s6): S163–S173. doi:10.1046/j.1440-6047.11.s.6.5.. Retrieved on 2007-02-09.
- ^ NIH Medline Plus. MedlinePlus Herbs and Supplements: Omega-3 fatty acids, fish oil, alpha-linolenic acid. Retrieved on February 14, 2006.
| Autacoids, unsaturated fatty acids: Eicosanoids | |
|---|---|
| Prostanoids | Prostaglandins - Thromboxanes (A2, B2) |
| Other | Arachidonic acids - Eicosapentaenoic acid - Leukotrienes - Lipoxins |
| Lipids: fatty acids | |
|---|---|
| Saturated | Butyric - Hexanoic - Caprylic - Decanoic - Lauric - Myristic - Palmitic - Stearic - Arachidic - Behenic |
| Omega-3 fatty acid | Alpha-linolenic - Stearidonic acid - Eicosapentaenoic acid - Docosahexaenoic acid |
| Omega-6 fatty acid | Linoleic - Gamma-Linolenic acid - Dihomo-gamma-linolenic acid - Arachidonic |
| Omega-9 fatty acid | Oleic - Erucic |
Categories: Fatty acids | Carboxylic acids
The content of this section is licensed under the GNU Free Documentation License (local copy). It uses material from the Wikipedia article "Eicosapentaenoic acid" modified October 27, 2007 with previous authors listed in its history.
