Eicosapentaenoic acid
IUPAC name	(5Z,8Z,11Z,14Z,17Z)-icosa-  5,8,11,14,17-pentaenoic acid
Identifiers
CAS number	[1553-41-9]
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

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. Image File history File links Download high-resolution version (1385x169, 5 KB) Chemical structure of Eicosapentaenoic acid created with ChemDraw. ... IUPAC nomenclature is a system of naming chemical compounds and of describing the science of chemistry in general. ... CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences, mixtures and alloys. ... The simplified molecular input line entry specification or SMILES is a specification for unambiguously describing the structure of chemical molecules using short ASCII strings. ... A chemical formula is an easy way of expressing information about the atoms that constitute a particular chemical compound. ... Molar mass is the mass of one mole of a chemical element or chemical compound. ... The plimsoll symbol as used in shipping In chemistry, the standard state of a material is its state at 1 bar (100 kilopascals exactly). ... For an explanation of n and numerical nomenclature (such as n−3 or 18:3), see Nomenclature of fatty acids. ... Structure of a carboxylic acid The 3D structure of the carboxyl group A space-filling model of the carboxyl group Carboxylic acids are organic acids characterized by the presence of a carboxyl group, which has the formula -C(=O)OH, usually written -COOH or -CO2H. [1] Carboxylic acids are Bronsted... For other uses, see Carbon (disambiguation). ... CIS usually refers to: Commonwealth of Independent States, a modern-day political entity consisting of 11 former Soviet Union Republics CIS is also an acronym for: Canadian Interuniversity Sport Cancer Information Service Carcinoma in situ Centre for Independent Studies Center for Immigration Studies Chinese International School Cisalpino Citizenship & Immigration Services...

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). Metabolites are the intermediates and products of metabolism. ... Arachidonic acid (AA) is an omega-6 fatty acid 20:4(ω-6). ... The actions of the ω-3 and ω-6 essential fatty acids (EFAs) are best characterized by their interactions; they cannot be understood separately. ... A polyunsaturated organic compound is one in which more than one double bond exists within the representative molecule. ... Not to be confused with fats. ... E1 - Alprostadil I2 - Prostacyclin A prostaglandin is any member of a group of lipid compounds that are derived enzymatically from fatty acids and have important functions in the animal body. ... A 250 ml bag of newly collected platelets. ... Thromboxane A2 Thromboxane B2 Thromboxane is a member of the family of lipids known as eicosanoids. ... Leukotrienes are autocrine and paracrine eicosanoid lipid mediators derived from arachidonic acid by 5-lipoxygenase. ... In biochemistry, eicosanoids are a class of oxygenated hydrophobic hormones that largely function as paracrine mediators. ...

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. Opsophagos was an ancient Greek term used to describe one who exhibited a seemingly uncontrollable desire for fish. ... Fish Oil is oil derived from fishes. ... COD may refer to many different topics, including: Cash on delivery Completion of discharge, shipping College of DuPage, a public Junior College with campuses in the suburbs of Chicago Call of Duty (series), a series of computer games Canadian Oxford Dictionary Carrier onboard delivery Catastrophic optical damage, a failure mode... Species Clupea alba Clupea bentincki Clupea caspiopontica Clupea chrysotaenia Clupea elongata Clupea halec Clupea harengus Clupea inermis Clupea leachii Clupea lineolata Clupea minima Clupea mirabilis Clupea pallasii Clupea sardinacaroli Clupea sulcata Herrings are small, oily fish of the genus Clupea found in the shallow, temperate waters of the North Atlantic... Mackerel is a common name applied to a number of different species of fish, mostly, but not exclusively, from the family Scombridae. ... For other uses, see Salmon (disambiguation). ... The menhadens comprise two genera of marine fish in the family Clupeidae. ... Sardines in the Pacific An open Sardines can Sardines on a plate grilled Sardines For the hide and seek-like game, see Hide and seek. ... Breast milk usually refers to the milk produced by a human female which is usually fed to infants, toddlers, and young children by breastfeeding. ...

However, fish do not naturally produce EPA, but obtain it from the algae they consume.^[1] It is available from some non-animal sources—spirulina and 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 derrived from it, are excellent alternative sources of EPA and other fatty acids, since fish often contain toxins due to pollution.^[4] For the programming language, see algae (programming language). ... Species About 35. ... Microalgae are the most primitive form of plants. ... Binomial name Portulaca oleracea L. Purslane, also known as Little Hogweed or Pusley, is an annual succulent in the Portulacaceae family. ...

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 α-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.^[5] For the programming language, see algae (programming language). ... In chemistry a precursor is a compound that participates in the chemical reaction that produces another compound. ... Docosahexaenoic acid (commonly known as DHA; 22:6(ω-3), all-cis-docosa-4,7,10,13,16,19-hexaenoic acid; trivial name cervonic acid) is an omega-3 essential fatty acid. ... For the disease characterized by excretion of large amounts of very dilute urine, see diabetes insipidus. ...

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.^[6] Most of these involve its ability to lower inflammation. The National Institutes of Health is an institution of the United States government which focuses on medical research. ... An abscess on the skin, showing the redness and swelling characteristic of inflammation. ...

Among omega-3 fatty acids, in particular EPA is thought to possess beneficial potential in mental conditions, such as schizophrenia.^[7][8] Several studies report an additional reduction in scores on symptom scales used to assess the severity of symptoms, when additional EPA is taken. Omega-3 fatty acids are polyunsaturated fatty acids found in certain fish tissues, and in vegetable sources such as flax seeds, walnuts, and canola oil. ...

Recent studies have suggested that EPA may effect depression, and importantly, suicidal behavior. One such study,^[9] 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.

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] Cytochrome P450 2C9 (abbreviated CYP2C9), a member of the cytochrome P450 mixed-function oxidase system, is involved in the metabolism of xenobiotics in the body. ... Cytochrome P450 2C19 (abbreviated CYP2C19), a member of the cytochrome P450 mixed-function oxidase system, is involved in the metabolism of xenobiotics in the body. ... Cytochrome P450 2D6 (CYP2D6), a member of the cytochrome P450 mixed-function oxidase system, is one of the most important enzymes involved in the metabolism of xenobiotics in the body. ... Cytochrome P450 3A4 (abbreviated CYP3A4) (EC 1. ...

See also

• Chlorella
• Cyanobacteria
• Docosahexaenoic acid
• List of omega-3 fatty acids
• Polyunsaturated fatty acids
• Snake oil

Species Chlorella vulgaris pyrenoidosa Chlorella pyrenoidosa Chlorella is a genus of single-celled green algae, belonging to the phylum Chlorophyta. ... Orders The taxonomy is currently under revision. ... Docosahexaenoic acid (commonly known as DHA; 22:6(ω-3), all-cis-docosa-4,7,10,13,16,19-hexaenoic acid; trivial name cervonic acid) is an omega-3 essential fatty acid. ... Essential fatty acid Essential nutrient (note: not all listed above are classified as essential nutrients) Categories: | | ... A polyunsaturated fatty acid (PUFA) is a class of unsaturated fat that contains more than one double bond. ... This article is about medicinal compounds. ...

References

Salmon is a rich source of EPA.

1. ^ Yvonne Bishop-Weston. Plant based sources of vegan & vegetarian Docosahexaenoic acid - DHA and Eicosapentaenoic acid EPA & Essential Fats. Retrieved on 2008-08-05.
2. ^ Jess Halliday (12/01/2007). Water 4 to introduce algae DHA/EPA as food ingredient. Retrieved on 2007-02-09.
3. ^ Simopoulos, Artemis P (2002). "Omega-3 fatty acids in wild plants, nuts and seeds" (^{[dead link]}). Asia Pacific Journal of Clinical Nutrition 11 (s6): S163–S173. doi:10.1046/j.1440-6047.11.s.6.5.. 
4. ^ Yvonne Bishop-Weston. Plant based sources of vegan & vegetarian Docosahexaenoic acid - DHA and Eicosapentaenoic acid EPA & Essential Fats. Retrieved on 2008-08-05.
5. ^ http://www.foodsforlife.org.uk/nutrition/vegetarian-DHA-EPA.html
6. ^ NIH Medline Plus. MedlinePlus Herbs and Supplements: Omega-3 fatty acids, fish oil, alpha-linolenic acid. Retrieved on February 14, 2006.
7. ^ Peet M, Brind J, Ramchand CN, Shah S, Vankar GK (2001). "Two double-blind placebo-controlled pilot studies of eicosapentaenoic acid in the treatment of schizophrenia". Schizophrenia Research 49 (3): 243–51. doi:10.1016/S0920-9964(00)00083-9. PMID 11356585. 
8. ^ Song C., Zhao S. Omega-3 fatty acid eicosapentaenoic acid. A new treatment for psychiatric and neurodegenerative diseases: a review of clinical investigations. University of Prince Edward Island, Department of Biomedical Sciences, AVC, 550 University Avenue, Charlottetown, PE, Canada. cai.song@nrc.gc.ca (Expert Opin Investig Drugs. 2007 Oct;16(10):1627-38.) Pub-Med
9. ^ Huan M, Hamazaki K, Sun Y, Itomura M, Liu H, Kang W, Watanabe S, Terasawa K, Hamazaki T. (2004). "Suicide attempt and n-3 fatty acid levels in red blood cells: a case control study in China." (abstract). Biological psychiatry 56 (7): 490-6. doi:10.1016/j.biopsych.2004.06.028. PMID 1540784. 
10. ^ Yao HT, Chang YW, Lan SJ, Chen CT, Hsu JT, Yeh TK (2006). "The inhibitory effect of polyunsaturated fatty acids on human CYP enzymes". Life Sci. 79 (26): 2432–40. doi:10.1016/j.lfs.2006.08.016. PMID 16978661.