Arachidonic acid - wikipedia Arachidonic acid Arachidonic acid Names IUPAC name ( 5Z, 8Z, 11Z, 14Z ) - 5, 8, 11, 14 - Eicosatetraenoic acid Systematic IUPAC name ( 5Z, 8Z, 11Z, 14Z ) - Icosa - 5, 8, 11, 14 - tetraenoic acid Other names 5, 8, 11, 14 - all - cis - Eicosatetraenoic acid ; all - cis - 5, 8, 11, 14 - Eicosatetraenoic acid ; Arachidonate Identifiers CAS Number 506 - 32 - 1 3D model ( JSmol ) Interactive image 3DMet B00061 Beilstein Reference 1713889 ChEBI CHEBI : 15843 ChemSpider 392692 DrugBank DB04557 ECHA InfoCard 100.007. 304 EC Number 208 - 033 - 4 IUPHAR / BPS 2391 KEGG C00219 MeSH Arachidonic + acid PubChem CID 444899 RTECS number CE6675000 UNII 27YG812J1I InChI InChI = 1S / C20H32O2 / c1 - 2 - 3 - 4 - 5 - 6 - 7 - 8 - 9 - 10 - 11 - 12 - 13 - 14 - 15 - 16 - 17 - 18 - 19 - 20 ( 21 ) 22 / h6 - 7, 9 - 10, 12 - 13, 15 - 16H, 2 - 5, 8, 11, 14, 17 - 19H2, 1H3, ( H, 21, 22 ) Key : YZXBAPSDXZZRGB - UHFFFAOYSA - N InChI = 1S / C20H32O2 / c1 - 2 - 3 - 4 - 5 - 6 - 7 - 8 - 9 - 10 - 11 - 12 - 13 - 14 - 15 - 16 - 17 - 18 - 19 - 20 ( 21 ) 22 / h6 - 7, 9 - 10, 12 - 13, 15 - 16H, 2 - 5, 8, 11, 14, 17 - 19H2, 1H3, ( H, 21, 22 ) / b7 - 6 -, 10 - 9 -, 13 - 12 -, 16 - 15 - Key : YZXBAPSDXZZRGB - DOFZRALJSA - N SMILES CCCCC / C = C C / C = C C / C = C C / C = C CCCC ( = O ) O Properties Chemical formula Molar mass 304.47 g mol Density 0.922 g / cm Melting point − 49 ° C ( − 56 ° F ; 224 K ) Boiling point 169 to 171 ° C ( 336 to 340 ° F ; 442 to 444 K ) at 0.15 mmHg log P 6.994 Acidity ( pK ) 4.752 Hazards R - phrases ( outdated ) R19 NFPA 704 0 Flash point 113 ° C ( 235 ° F ; 386 K ) Related compounds Related compounds Eicosatetraenoic acid Except where otherwise noted, data are given for materials in their standard state ( at 25 ° C ( 77 ° F ), 100 kPa ). N verify ( what is ? ) Infobox references Arachidonic acid ( AA, sometimes ARA ) is a polyunsaturated omega - 6 fatty acid 20 : 4 ( ω - 6 ). It is structurally related to the saturated arachidic acid found in Cupuaçu butter ( L. arachis -- peanut ). Contents 1 Chemistry 2 Biology 3 Conditionally essential fatty acid 4 The synthesis and cascade in humans 4.1 PLA activation 4.2 PLC activation 5 In the body 5.1 Muscle growth 5.2 Brain 5.3 Alzheimer 's disease 5.4 Bodybuilding supplement 6 Dietary arachidonic acid and inflammation 7 Health effects of arachidonic acid supplementation 8 See also 9 References 10 External links Chemistry In chemical structure, arachidonic acid is a carboxylic acid with a 20 - carbon chain and four cis - double bonds ; the first double bond is located at the sixth carbon from the omega end. Some chemistry sources define ' arachidonic acid ' to designate any of the eicosatetraenoic acids. However, almost all writings in biology, medicine and nutrition limit the term to all - cis - 5, 8, 11, 14 - eicosatetraenoic acid. Biology Arachidonic acid is a polyunsaturated fatty acid present in the phospholipids ( especially phosphatidylethanolamine, phosphatidylcholine, and phosphatidylinositides ) of membranes of the body 's cells, and is abundant in the brain, muscles, and liver. Skeletal muscle is an especially active site of arachidonic acid retention, accounting for roughly 10 - 20 % of the phospholipid fatty acid content on average. In addition to being involved in cellular signaling as a lipid second messenger involved in the regulation of signaling enzymes, such as PLC - γ, PLC - δ, and PKC - α, - β, and - γ isoforms, arachidonic acid is a key inflammatory intermediate and can also act as a vasodilator. ( Note separate synthetic pathways, as described in section below. ) Conditionally essential fatty acid Main article : Essential fatty acid § Essentiality Arachidonic acid in the human body usually comes from dietary animal sources -- meat, eggs, dairy -- or is synthesized from linoleic acid. Arachidonic acid is not one of the essential fatty acids. However, it does become essential if there is a deficiency in linoleic acid or if there is an inability to convert linoleic acid to arachidonic acid, which is required by most mammals. Some mammals lack the ability to -- or have a very limited capacity to -- convert linoleic acid into arachidonic acid, making it an essential part of their diets. Since little or no arachidonic acid is found in common plants, such animals are obligate carnivores ; the cat is a common example. A commercial source of arachidonic acid has been derived, however, from the fungus Mortierella alpina. The synthesis and cascade in humans Eicosanoid synthesis. Arachidonic acid is freed from a phospholipid molecule by the enzyme phospholipase A2 ( PLA ), which cleaves off the fatty acid, but can also be generated from DAG by diacylglycerol lipase. Arachidonic acid generated for signaling purposes appears to be derived by the action of group IVA cytosolic phospholipase A2 ( cPLA, 85 kDa ), whereas inflammatory arachidonic acid is generated by the action of a low - molecular - weight secretory PLA ( sPLA, 14 - 18 kDa ). Arachidonic acid is the precursor that is metabolized by various enzymes to a wide range of biologically and clinically important eicosanoids and metabolites of these eicosanoids : The enzymes cyclooxygenase - 1 and - 2 ( i.e. prostaglandin G / H synthase 1 and 2 ( PTGS1 and PTGS2 ) ) metabolize arachidonic acid to Prostaglandin G2 and prostaglandin H2, which in turn may be converted to various prostaglandins, to prostacyclin, to thromboxanes, and to the 17 - carbon product of thromboxane metabolism of prostaglandin G2 / H2, 12 - Hydroxyheptadecatrienoic acid ( 12 - HHT ). The enzyme 5 - lipoxygenase metabolizes arachidonic acid to 5 - hydroperoxyicosatetraenoic acid ( 5 - HPETE ), which in turn is metabolized to various leukotrienes ( i.e. leukotriene B4, leukotriene C4, leukotriene D4, and leukotriene E4 as well as to 5 - hydroxyicosatetraenoic acid ( 5 - HETE ) which may then be further metabolized to 5 - HETE 's more potent 5 - keto analog, 5 - oxo - eicosatetraenoic acid ( 5 - oxo - ETE ) ( also see 5 - Hydroxyicosatetraenoic acid. The enzymes 15 - lipoxygenase - 1 ( ALOX15 and 15 - lipoxygenase - 2 ( ALOX15B metabolize arachidonic acid to 15 - hydroperoxyicosatetraemoic acid ( 15 - HPETE ) which may then be further metabolized to 15 - hydroxyicosatetraenoic acid ( 15 - HETE ) and lipoxins ; 15 - Lipoxygenase - 1 may also further metabolize 15 - HPETE to eoxins in a pathway analogous to ( and presumably using the same enzymes as used in ) the pathway which metabolizes 5 - HPETE to leukotrienes. The enzyme 12 - lipoxygenase ( ALOX12 ) metabolizes arachidonic acid to 12 - hydroperoxyeicosatetraenoic acid ( 12 - HPETE0 which may then be metabolized to 12 - hydroxyeicosatetraenoic acid ( 12 - HETE ) and to hepoxilins. Arachidonic acid is also used in the biosynthesis of anandamide. Some arachidonic acid is converted into hydroxyeicosatetraenoic acids ( HETEs ) and epoxyeicosatrienoic acids ( EETs ) by epoxygenase. The production of these derivatives and their action in the body are collectively known as the `` arachidonic acid cascade '' ; see essential fatty acid interactions and the enzyme and metabolite linkages given in the previous paragraph for more details. PLA activation Further information : Phospholipase_A2 § Regulation PLA, in turn, is activated by ligand binding to receptors, including : 5 - HT2 receptors mGLUR1 bFGF receptor IFN - α receptor IFN - γ receptor Furthermore, any agent increasing intracellular calcium may cause activation of some forms of PLA. PLC activation Further information : Phospholipase C § Activation Alternatively, arachidonic acid may be cleaved from phospholipids after phospholipase C ( PLC ) cleaves off the inositol trisphosphate group, yielding diacylglycerol ( DAG ), which subsequently is cleaved by DAG lipase to yield arachidonic acid. Receptors that activate this pathway include : A1 receptor D2 receptor α - 2 adrenergic receptor 5 - HT1 receptor PLC may also be activated by MAP kinase. Activators of this pathway include PDGF and FGF. In the body Muscle growth Arachidonic acid promotes the repair and growth of skeletal muscle tissue via conversion to prostaglandin PGF2alpha during and following physical exercise. PGF2alpha promotes muscle protein synthesis by signaling through the Akt / mTOR pathway, similar to leucine, β - hydroxy β - methylbutyric acid, and phosphatidic acid. Brain Arachidonic acid is one of the most abundant fatty acids in the brain, and is present in similar quantities to docosahexaenoic acid ( DHA ). The two account for approximately 20 % of its fatty acid content. Like DHA, neurological health is reliant upon sufficient levels of arachidonic acid. Among other things, arachidonic acid helps to maintain hippocampal cell membrane fluidity. It also helps protect the brain from oxidative stress by activating peroxisome proliferator - activated receptor gamma. ARA also activates syntaxin - 3 ( STX - 3 ), a protein involved in the growth and repair of neurons. Arachidonic acid is also involved in early neurological development. In one study funded by the U.S. National Institute of Child Health and Human Development, infants ( 18 months ) given supplemental arachidonic acid for 17 weeks demonstrated significant improvements in intelligence, as measured by the Mental Development Index. This effect is further enhanced by the simultaneous supplementation of ARA with DHA. In adults, the disturbed metabolism of ARA contributes to neurological disorders such as Alzheimer 's disease and Bipolar disorder. This involves significant alterations in the conversion of arachidonic acid to other bioactive molecules ( overexpression or disturbances in the ARA enzyme cascade ). Alzheimer 's disease Studies on arachidonic acid and the pathogenesis of Alzheimer 's disease is mixed, with one study of AA and its metabolites that suggests they are associated with the onset of Alzheimer 's disease, whereas another study suggests that the supplementation of arachidonic acid during the early stages of this disease may be effective in reducing symptoms and slowing the disease progress. Additional studies on arachidonic acid supplementation for Alzheimer 's patients are needed. Another study indicates that air pollution is the source of inflammation and arachidonic acid metabolites promote the inflammation to signal the immune system of the cell damage. Bodybuilding supplement Arachidonic acid is marketed as an anabolic bodybuilding supplement in a variety of products. Supplementation of arachidonic acid ( 1,500 mg / day for 8 weeks ) has been shown to increase lean body mass, strength, and anaerobic power in experienced resistance - trained men. This was demonstrated in a placebo - controlled study at the University of Tampa. Thirty men ( aged 20.4 ± 2.1 years ) took arachidonic acid or a placebo for 8 weeks, and participated in a controlled resistance - training program. After 8 weeks, Lean Body Mass ( LBM ) had increased significantly, and to a greater extent, in the ARA group ( 1.62 kg ) vs. placebo ( 0.09 kg ) ( p < 0.05 ). The change in muscle thickness was also greater in the ARA group (. 47 cm ) than placebo (. 25 cm ) ( p < 0.05 ). Wingate anaerobic power increased to a greater extent in ARA group as well ( 723.01 to 800.66 W ) vs. placebo ( 738.75 to 766.51 W ). Lastly, the change in total strength was significantly greater in the ARA group ( 109.92 lbs. ) compared to placebo ( 75.78 lbs. ). These results suggest that ARA supplementation can positively augment adaptations in strength and skeletal muscle hypertrophy in resistance - trained men. An earlier clinical study examining the effects of 1,000 mg / day of arachidonic acid for 50 days found supplementation to enhance anaerobic capacity and performance in exercising men. During this study, a significant group -- time interaction effect was observed in Wingate relative peak power ( AA : 1.2 ± 0.5 ; P : - 0.2 ± 0.2 W kg - 1, p = 0.015 ). Statistical trends were also seen in bench press 1RM ( AA : 11.0 ± 6.2 ; P : 8.0 ± 8.0 kg, p = 0.20 ), Wingate average power ( AA : 37.9 ± 10.0 ; P : 17.0 ± 24.0 W, p = 0.16 ), and Wingate total work ( AA : 1292 ± 1206 ; P : 510 ± 1249 J, p = 0.087 ). AA supplementation during resistance - training promoted significant increases in relative peak power with other performance related variables approaching significance. These findings support the use of AA as an ergogenic. Dietary arachidonic acid and inflammation Increased consumption of arachidonic acid will not cause inflammation during normal metabolic conditions unless lipid peroxidation products are mixed in. Arachidonic acid is metabolized to both proinflammatory and anti-inflammatory eicosanoids during and after the inflammatory response, respectively. Arachidonic acid is also metabolized to inflammatory and anti-inflammatory eicosanoids during and after physical activity to promote growth. However chronic inflammation from exogenous toxins and excessive exercise should not be confused with acute inflammation from exercise and sufficient rest that is required by the inflammatory response to promote the repair and growth of the micro tears of tissues. However, the evidence is mixed. Some studies giving between 840 mg and 2,000 mg per day to healthy individuals for up to 50 days have shown no increases in inflammation or related metabolic activities. However, others show that increased arachidonic acid levels are actually associated with reduced pro-inflammatory IL - 6 and IL - 1 levels and increased anti-inflammatory tumor necrosis factor - beta. This may result in a reduction in systemic inflammation. Arachidonic acid does still play a central role in inflammation related to injury and many diseased states. How it is metabolized in the body dictates its inflammatory or anti-inflammatory activity. Individuals suffering from joint pains or active inflammatory disease may find that increased arachidonic acid consumption exacerbates symptoms, presumably because it is being more readily converted to inflammatory compounds. Likewise, high arachidonic acid consumption is not advised for individuals with a history of inflammatory disease, or who are in compromised health. Of note, while ARA supplementation does not appear to have proinflammatory effects in healthy individuals, it may counter the anti-inflammatory effects of omega - 3 fatty acid supplementation. Health effects of arachidonic acid supplementation Arachidonic acid supplementation in daily dosages of 1,000 -- 1,500 mg for 50 days has been well tolerated during several clinical studies, with no significant side effects reported. All common markers of health, including kidney and liver function, serum lipids, immunity, and platelet aggregation appear to be unaffected with this level and duration of use. Furthermore, higher concentrations of ARA in muscle tissue may be correlated with improved insulin sensitivity. Arachidonic acid supplementation of the diets of healthy adults appears to offer no toxicity or significant safety risk. While studies looking at arachidonic acid supplementation in sedentary subjects have failed to find changes in resting inflammatory markers in doses up to 1,500 mg daily, strength - trained subjects may respond differently. One study at Baylor University reported a significant reduction in resting inflammation ( via marker IL - 6 ) in young men supplementing 1,000 mg / day of arachidonic acid for 50 days in combination with resistance training. This suggests that rather being pro-inflammatory, supplementation of ARA while undergoing resistance training may actually improve the regulation of systemic inflammation. A meta - analysis by Cambridge University looking for associations between heart disease risk and individual fatty acids reported a significantly reduced risk of heart disease with higher levels of EPA and DHA ( Omega - 3 fats ), as well as the Omega - 6 Arachidonic Acid. A scientific advisory from the American Heart Association has also favorably evaluated the health impact of dietary omega - 6 fats, including arachidonic acid. The group does not recommend limiting this essential fatty acid. In fact, the paper recommends individuals follow a diet that consists of at least 5 -- 10 % of calories coming from omega - 6 fats, including arachidonic acid. It suggests dietary ARA is not a risk factor for heart disease, and may play a role in maintaining optimal metabolism and reduced heart disease risk. It is, therefore, recommended to maintain sufficient intake levels of both omega - 3 and omega - 6 fatty acids for optimal health. Arachidonic acid is not carcinogenic, and studies show dietary level is not associated ( positively or negatively ) with risk of cancers. ARA remains integral to the inflammatory and cell growth process, however, which is disturbed in many types of disease including cancer. Therefore, the safety of arachidonic acid supplementation in patients suffering from cancer, inflammatory, or other diseased states is unknown, and supplementation is not recommended. See also Aspirin -- inhibits cyclooxygenase enzyme, preventing conversion of arachidonic acid to other signal molecules Fish oil Polyunsaturated fat Polyunsaturated fatty acid References Jump up ^ Pubchem. `` 5, 8, 11, 14 - Eicosatetraenoic acid C20H32O2 - PubChem ''. pubchem.ncbi.nlm.nih.gov. Retrieved 2016 - 03 - 31. Jump up ^ `` Dorland 's Medical Dictionary -- ' A ' ''. Archived from the original on 11 January 2007. Retrieved 2007 - 01 - 12. 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External links Arachidonic Acid at acnp.org Arachidonic Acid at the US National Library of Medicine Medical Subject Headings ( MeSH ) Eicosanoids Precursor Arachidonic acid Prostanoids Prostaglandins ( PG ) Precursor Active D / J E / F E ( Dinoprostone ) E ( Alprostadil ) F ( Dinoprost ) : I I ( Prostacyclin / Epoprostenol ) : Thromboxanes ( TX ) Leukotrienes ( LT ) Precursor Arachidonic acid 5 - hydroperoxide Initial SRS - A Eoxins ( EX ) Precursor Arachidonic acid 15 - hydroperoxide Eoxins Nonclassic Lipoxins ( LX ) ( A, B ) Virodhamine By function bronchoconstriction PGD TXA LTC LTD LTE vasoconstriction PGF TXA TXB ) vasodilation PGE PGI LTC LTD LTE platelets : induce TXA inhibit PGD PGI leukocytes : induce TXA LTB inhibit PGD PGE fever stimulation : PGE labor stimulation : PGE ( Dinoprostone ) PGF ( Dinoprost ) Lipids : fatty acids Saturated Butyric ( C4 ) Valeric ( C5 ) Caproic ( C6 ) Enanthic ( C7 ) Caprylic ( C8 ) Pelargonic ( C9 ) Capric ( C10 ) Undecylic ( C11 ) Lauric ( C12 ) Tridecylic ( C13 ) Myristic ( C14 ) Pentadecanoic ( C15 ) Palmitic ( C16 ) Margaric ( C17 ) Stearic ( C18 ) Nonadecylic ( C19 ) Arachidic ( C20 ) Heneicosylic ( C21 ) Behenic ( C22 ) Tricosylic ( C23 ) Lignoceric ( C24 ) Pentacosylic ( C25 ) Cerotic ( C26 ) Heptacosylic ( C27 ) Montanic ( C28 ) Nonacosylic ( C29 ) Melissic ( C30 ) Hentriacontylic ( C31 ) Lacceroic ( C32 ) Psyllic ( C33 ) Geddic ( C34 ) Ceroplastic ( C35 ) Hexatriacontylic ( C36 ) Heptatriacontanoic ( C37 ) Octatriacontanoic ( C38 ) ω − 3 Unsaturated α - Linolenic ( 18 : 3 ) Stearidonic ( 18 : 4 ) Eicosapentaenoic ( 20 : 5 ) Docosahexaenoic ( 22 : 6 ) ω − 6 Unsaturated Linoleic ( 18 : 2 ) γ - Linolenic ( 18 : 3 ) Dihomo - γ - linolenic ( 20 : 3 ) Arachidonic ( 20 : 4 ) Adrenic ( 22 : 4 ) Osbond ( 22 : 5 ) ω − 7 Unsaturated Palmitoleic ( 16 : 1 ) Vaccenic ( 18 : 1 ) Paullinic ( 20 : 1 ) ω − 9 Unsaturated Oleic ( 18 : 1 ) Elaidic ( trans - 18 : 1 ) Gondoic ( 20 : 1 ) Erucic ( 22 : 1 ) Nervonic ( 24 : 1 ) Mead ( 20 : 3 ) Biological activity Leukotriene signaling modulators Receptor ( ligands ) BLT BLT Agonists : 12 - HETE 20 - Hydroxy - LTB Leukotriene B LY - 255283 Antagonists : 20 - Carboxy - LTB Amelubant CGS - 23131 ( LY - 223982 ) CGS - 25019C CP - 105696 CP - 195543 Etalocib LY - 293111 Moxilubant ONO - 4057 RG - 14893 RP - 69698 SB - 209247 SC - 53228 Ticolubant U-75302 ZK - 158252 BLT Agonists : 12 - HETE 12 - HHT 12 - HpETE 15 - HETE 15 - HpETE 20 - Hydroxy - LTB Leukotriene B Antagonists : CP - 195543 LY - 255283 ZK - 158252 CysLT CysLT Agonists : Leukotriene C Leukotriene D Leukotriene E Antagonists : Ablukast BAYu9773 BAYu9916 BAYx7195 Cinalukast FPL - 55712 ICI - 198615 Iralukast LY - 170680 Masilukast MK - 571 Montelukast ONO - 1078 Pobilukast Pranlukast Ritolukast SKF - 104353 SR - 2640 Sulukast Tipelukast Tomelukast Verlukast Zafirlukast ZD - 3523 CysLT Agonists : Leukotriene C Leukotriene D Leukotriene E Antagonists : BAYu9773 BAYu9916 CysLT Agonists : Leukotriene E Enzyme ( inhibitors ) 5 - LOX 2 - TEDC Baicalein BW - A4C BW - B70C Caffeic acid CDC CJ - 13610 Curcumin Fenleuton Hyperforin Hypericum perforatum ( St. John 's Wort ) Meclofenamic acid ( meclofenamate ) Minocycline N - Stearoyldopamine Timegadine Zileuton FLAP inhibitors : AM - 103 AM - 679 BAYx1005 MK - 591 MK - 886 12 - LOX 2 - TEDC 3 - Methoxytropolone Baicalein CDC 15 - LOX 2 - TEDC CDC Luteolin PD - 146176 LTA H Acebilustat Captopril DG - 051 Fosinoprilat JNJ - 26993135 SA - 6541 SC - 57461A Ubenimex ( bestatin ) LTB H 17 - Octadecynoic acid LTC S Azelastine MK - 886 LTC H Acivicin Serine - borate complex LTD Cilastatin Ubenimex ( bestatin ) Others Precursors : Linoleic acid γ - Linolenic acid ( gamolenic acid ) Dihomo - γ - linolenic acid Diacylglycerol Arachidonic acid 5 - HPETE ( arachidonic acid 5 - hydroperoxide ) Leukotriene A See also Receptor / signaling modulators Prostanoid signaling modulators Nuclear receptor modulators PPAR modulators PPARα Agonists : 15 - HETE 15 - HpETE Aleglitazar Aluminium clofibrate Arachidonic acid Bezafibrate Clofibrate CP - 775146 Daidzein DHEA ( prasterone ) ( in rodents ) Elafibranor Etomoxir Fenofibrate Genistein Gemfibrozil GW - 7647 Leukotriene B LG - 101506 LG - 100754 Lobeglitazone Muraglitazar Oleylethanolamide Palmitoylethanolamide Pemafibrate Perfluorononanoic acid Perfluorooctanoic acid Pioglitazone Saroglitazar Sodelglitazar Tesaglitazar Tetradecylthioacetic acid Troglitazone WY - 14643 Antagonists : GW - 6471 MK - 886 PPARδ Agonists : 15 - HETE 15 - HpETE Arachidonic acid Bezafibrate Daidzein Elafibranor Fonadelpar Genistein GW - 0742 GW - 501516 L - 165,041 LG - 101506 MBX - 8025 Sodelglitazar Tetradecylthioacetic acid Antagonists : FH - 535 GSK - 0660 GSK - 3787 PPARγ Agonists : 5 - Oxo - ETE 5 - Oxo - 15 - hydroxy - ETE 15 - Deoxy - Δ - prostaglandin J 15 - HETE 15 - HpETE Aleglitazar Arachidonic acid Balaglitazone Berberine Bezafibrate Cevoglitazar Ciglitazone Daidzein Darglitazone Edaglitazone Efatutazone Englitazone Etalocib Farglitazar Genistein GW - 1929 Ibuprofen Imiglitazar Indeglitazar LG - 100268 LG - 100754 LG - 101506 Lobeglitazone Muraglitazar ( muroglitazar ) nTZDpa Naveglitazar Netoglitazone Oxeglitazar Peliglitazar Pemaglitazar Perfluorononanoic acid Pioglitazone Prostaglandin J Ragaglitazar Reglitazar Rivoglitazone Rosiglitazone RS5444 Saroglitazar Sipoglitazar Sodelglitazar Telmisartan Tesaglitazar Troglitazone SPPARMs : BADGE EPI - 001 INT - 131 MK - 0533 S26948 Antagonists : FH - 535 GW - 9662 SR - 202 T - 0070907 Unknown : SR - 1664 Non-selective Agonists : Ciprofibrate Clinofibrate Clofibride Englitazone Etofibrate Farglitazar Netoglitazone Ronifibrate Rivoglitazone Simfibrate Unsorted Agonists : Lanifibranor Seladelpar See also Receptor / signaling modulators Nuclear receptor modulators Prostanoid signaling modulators Receptor ( ligands ) DP ( D ) DP Agonists : Prostaglandin D Treprostinil Antagonists : Asapiprant Laropiprant Vidupiprant DP Agonists : Indometacin Prostaglandin D Antagonists : ADC - 3680 AZD - 1981 Bay U3405 Fevipiprant MK - 1029 MK - 7246 QAV - 680 Ramatroban Setipiprant Timapiprant TM30089 Vidupiprant EP ( E ) EP Agonists : Beraprost Enprostil Iloprost ( ciloprost ) Latanoprost Lubiprostone Misoprostol Prostaglandin E ( alprostadil ) Prostaglandin E ( dinoprostone ) Sulprostone Antagonists : AH - 6809 ONO - 8130 SC - 19220 SC - 51089 SC - 51322 EP Agonists : Butaprost Misoprostol Prostaglandin E ( alprostadil ) Prostaglandin E ( dinoprostone ) Treprostinil Antagonists : AH - 6809 PF - 04418948 TG 4 - 155 EP Agonists : Beraprost Carbacyclin Cicaprost Enprostil Iloprost ( ciloprost ) Isocarbacyclin Latanoprost Misoprostol Prostaglandin D Prostaglandin E ( alprostadil ) Prostaglandin E ( dinoprostone ) Remiprostol Sulprostone Antagonists : L - 798106 EP Agonists : Lubiprostone Misoprostol Prostaglandin E ( alprostadil ) Prostaglandin E ( dinoprostone ) TCS - 2510 Antagonists : Grapiprant GW - 627368 L - 161982 ONO - AE3 - 208 Unsorted Agonists : 16, 16 - Dimethyl Prostaglandin E Aganepag Carboprost Evatanepag Gemeprost Nocloprost Omidenepag Prostaglandin F ( dinoprost ) Simenepag Taprenepag FP ( F ) Agonists : Alfaprostol Bimatoprost Carboprost Cloprostenol Enprostil Fluprostenol Latanoprost Prostaglandin D Prostaglandin F ( dinoprost ) Sulotroban Tafluprost Travoprost Unoprostone IP ( I ) Agonists : ACT - 333679 AFP - 07 Beraprost BMY - 45778 Carbacyclin Cicaprost Iloprost ( ciloprost ) Isocarbacyclin MRE - 269 NS - 304 Prostacyclin ( prostaglandin I, epoprostenol ) Prostaglandin E ( alprostadil ) Ralinepag Selexipag Taprostene TRA - 418 Treprostinil Antagonists : RO1138452 TP ( TX ) Agonists : Carbocyclic thromboxane A I - BOP Thromboxane A U-46619 Vapiprost Antagonists : 12 - HETE 13 - APA AA - 2414 Argatroban Bay U3405 BMS - 180,291 Daltroban Domitroban EP - 045 GR - 32191 ICI - 185282 ICI - 192605 Ifetroban Imitrodast L - 655240 L - 670596 Linotroban Mipitroban ONO - 3708 ONO - 11120 Picotamide Pinane thromboxane A Ramatroban Ridogrel S - 145 Samixogrel Seratrodast SQ - 28,668 SQ - 29,548 Sulotroban Terbogrel Terutroban TRA - 418 Unsorted Arbaprostil Ataprost Ciprostene Clinprost Cobiprostone Delprostenate Deprostil Dimoxaprost Doxaprost Ecraprost Eganoprost Enisoprost Eptaloprost Esuberaprost Etiproston Fenprostalene Flunoprost Froxiprost Lanproston Limaprost Luprostiol Meteneprost Mexiprostil Naxaprostene Nileprost Nocloprost Ornoprostil Oxoprostol Penprostene Pimilprost Piriprost Posaraprost Prostalene Rioprostil Rivenprost Rosaprostol Spiriprostil Tiaprost Tilsuprost Tiprostanide Trimoprostil Viprostol Enzyme ( inhibitors ) COX ( PTGS ) Salicylic acids : Aloxiprin Aspirin ( acetylsalicylic acid ) Benorilate ( benorylate ) Carbasalate calcium Diflusinal Dipyrocetyl Ethenzamide Guacetisal Magnesium salicylate Mesalazine ( 5 - aminosalicylic acid ) Methyl salicylate Salacetamide Salicin Salicylamide Salicylate ( salicylic acid ) Salsalate Sodium salicylate Triflusal ; Acetic acids : Aceclofenac Acemetacin Aclofenac Amfenac Alclofenac Bendazac Bromfenac Bufexamac Bumadizone Cinmetacin Clometacin Diclofenac Difenpiramide Etodolac Felbinac Fenclofenac Fentiazac Glucametacin Indometacin ( indomethacin ) Indometacin farnesil Ketorolac Lonazolac Mofezolac Nabumetone Oxametacin Oxindanac Proglumetacin Sulindac Sulindac sulfide Tolmetin Zidometacin Zomepirac ; Propionic acids : Alminoprofen Benoxaprofen Bucloxic acid ( blucloxate ) Butibufen Carprofen Dexibuprofen Dexindoprofen Dexketoprofen Fenbufen Fenoprofen Flunoxaprofen Flurbiprofen Ibuprofen Ibuproxam Indoprofen Ketoprofen Loxoprofen Miroprofen Naproxen Naproxcinod Oxaprozin Pirprofen Pranoprofen Suprofen Tarenflurbil Tepoxalin Tiaprofenic acid ( tiaprofenate ) Vedaprofen ; Anthranilic acids ( fenamic acids ) : Etofenamic acid ( etofenamate ) Floctafenic acid ( floctafenate ) Flufenamic acid ( flufenamate ) Meclofenamic acid ( meclofenamate ) Mefenamic acid ( mefenamate ) Morniflumic acid ( morniflumate ) Niflumic acid ( niflumate ) Talinflumic acid ( talinflumate ) Tolfenamic acid ( tolfenamate ) ; Pyrazolones : Azapropazone Dipyrone Isopyrin Oxyphenbutazone Phenylbutazone ; Enolic acids ( oxicams ) : Ampiroxicam Droxicam Enolicam Isoxicam Lornoxicam Meloxicam Piroxicam Tenoxicam ; 4 - Aminoquinolines : Antrafenine Floctafenine Glafenine ; Quinazolines : Fluproquazone Proquazone ; Aminonicotinic acids : Clonixeril Clonixin Flunixin ; Sulfonanilides : Flosulide Nimesulide ; Aminophenols ( anilines ) : Acetanilide AM - 404 ( N - arachidonoylaminophenol ) Bucetin Paracetamol ( acetaminophen ) Parapropamol Phenacetin Propacetamol ; Selective COX - 2 inhibitors ( coxibs ) : Apricoxib Celecoxib Cimicoxib Deracoxib Etoricoxib Firocoxib Lumiracoxib Mavacoxib Parecoxib Polmacoxib Robenacoxib Rofecoxib Tilmacoxib Valdecoxib ; Others / unsorted : Anitrazafen Clobuzarit Curcumin DuP - 697 FK - 3311 Flumizole FR - 122047 Glimepiride Hyperforin Itazigrel L - 655240 L - 670596 Licofelone Menatetrenone ( vitamin K ) NCX - 466 NCX - 4040 NS - 398 Pamicogrel Resveratrol Romazarit Rosmarinic acid Rutecarpine Satigrel SC - 236 SC - 560 SC - 58125 Tenidap Tiflamizole Timegadine Trifenagrel Tropesin PGD S Retinoids Selenium ( selenium tetrachloride, sodium selenite, selenium disulfide ) PGES HQL - 79 PGFS Bimatoprost PGI S Tranylcypromine TXAS Camonagrel Dazmegrel Dazoxiben Furegrelate Isbogrel Midazogrel Nafagrel Nicogrelate Ozagrel Picotamide Pirmagrel Ridogrel Rolafagrel Samixogrel Terbogrel U63557A Others Precursors : Linoleic acid γ - Linolenic acid ( gamolenic acid ) Dihomo - γ - linolenic acid Diacylglycerol Arachidonic acid Prostaglandin G Prostaglandin H See also Receptor / signaling modulators Leukotriene signaling modulators Nuclear receptor modulators TRP channel modulators TRPA Activators 4 - Hydroxynonenal 4 - Oxo - 2 - nonenal 4, 5 - EET 12S - HpETE 15 - Deoxy - Δ - prostaglandin J2 α - Sanshool ( ginger, Sichuan and melegueta peppers ) Acrolein Allicin ( garlic ) Allyl isothiocyanate ( mustard, radish, horseradish, wasabi ) AM404 Bradykinin Cannabichromene ( cannabis ) Cannabidiol ( cannabis ) Cannabigerol ( cannabis ) Cinnamaldehyde ( cinnamon ) CR gas ( dibenzoxazepine ; DBO ) CS gas ( 2 - chlorobenzal malononitrile ) Curcumin ( turmeric ) Dehydroligustilide ( celery ) Diallyl disulfide Dicentrine ( Lindera spp. ) Farnesyl thiosalicylic acid Formalin Gingerols ( ginger ) Hepoxilin A3 Hepoxilin B3 Hydrogen peroxide Icilin Isothiocyanate Ligustilide ( celery, Angelica acutiloba ) Linalool ( Sichuan pepper, thyme ) Methylglyoxal Methyl salicylate ( wintergreen ) N - Methylmaleimide Nicotine ( tobacco ) Oleocanthal ( olive oil ) Paclitaxel ( Pacific yew ) Paracetamol ( acetaminophen ) PF - 4840154 Phenacyl chloride Polygodial ( Dorrigo pepper ) Shogaols ( ginger, Sichuan and melegueta peppers ) Tear gases Tetrahydrocannabinol ( cannabis ) Thiopropanal S - oxide ( onion ) Umbellulone ( Umbellularia californica ) WIN 55,212 - 2 Blockers Dehydroligustilide ( celery ) Nicotine ( tobacco ) Ruthenium red TRPC Activators Adhyperforin ( St John 's wort ) Diacyl glycerol GSK1702934A Hyperforin ( St John 's wort ) Substance P Blockers DCDPC DHEA - S Flufenamic acid GSK417651A GSK2293017A Meclofenamic acid N - ( p - amylcinnamoyl ) anthranilic acid Niflumic acid Pregnenolone sulfate Progesterone Pyr3 Tolfenamic acid TRPM Activators ADP - ribose BCTC Calcium ( intracellular ) Cold Coolact P Cooling Agent 10 CPS - 369 Eucalyptol ( eucalyptus ) Frescolat MGA Frescolat ML Geraniol Hydroxycitronellal Icilin Linalool Menthol ( mint ) PMD 38 Pregnenolone sulfate Rutamarin ( Ruta graveolens ) Steviol glycosides ( e.g., stevioside ) ( Stevia rebaudiana ) Sweet tastants ( e.g., glucose, fructose, sucrose ; indirectly ) Thio - BCTC WS - 3 WS - 12 WS - 23 Blockers Capsazepine Clotrimazole DCDPC Flufenamic acid Meclofenamic acid Mefenamic acid N - ( p - amylcinnamoyl ) anthranilic acid Nicotine ( tobacco ) Niflumic acid Ruthenium red Rutamarin ( Ruta graveolens ) Tolfenamic acid TPPO TRPML Activators MK6 - 83 PI ( 3, 5 ) P SF - 22 TRPP Activators Triptolide ( Tripterygium wilfordii ) Blockers Ruthenium red TRPV Activators 2 - APB 5 ', 6 ' - EET 9 - HODE 9 - oxoODE 12S - HETE 12S - HpETE 13 - HODE 13 - oxoODE 20 - HETE α - Sanshool ( ginger, Sichuan and melegueta peppers ) Allicin ( garlic ) AM404 Anandamide Bisandrographolide ( Andrographis paniculata ) Camphor ( camphor laurel, rosemary, camphorweed, African blue basil, camphor basil ) Cannabidiol ( cannabis ) Cannabidivarin ( cannabis ) Capsaicin ( chili pepper ) Carvacrol ( oregano, thyme, pepperwort, wild bergamot, others ) DHEA Diacyl glycerol Dihydrocapsaicin ( chili pepper ) Estradiol Eugenol ( basil, clove ) Evodiamine ( Euodia ruticarpa ) Gingerols ( ginger ) GSK1016790A Heat Hepoxilin A3 Hepoxilin B3 Homocapsaicin ( chili pepper ) Homodihydrocapsaicin ( chili pepper ) Incensole ( incense ) Lysophosphatidic acid Low pH ( acidic conditions ) Menthol ( mint ) N - Arachidonoyl dopamine N - Oleoyldopamine N - Oleoylethanolamide Nonivamide ( PAVA ) ( PAVA spray ) Nordihydrocapsaicin ( chili pepper ) Paclitaxel ( Pacific yew ) Paracetamol ( acetaminophen ) Phorbol esters ( e.g., 4α - PDD ) Piperine ( black pepper, long pepper ) Polygodial ( Dorrigo pepper ) Probenecid Protons Rutamarin ( Ruta graveolens ) Resiniferatoxin ( RTX ) ( Euphorbia resinifera / pooissonii ) Shogaols ( ginger, Sichuan and melegueta peppers ) Tetrahydrocannabivarin ( cannabis ) Thymol ( thyme, oregano ) Tinyatoxin ( Euphorbia resinifera / pooissonii ) Tramadol Vanillin ( vanilla ) Zucapsaicin Blockers α - Spinasterol ( Vernonia tweediana ) AMG - 517 Asivatrep BCTC Cannabigerol ( cannabis ) Cannabigerolic acid ( cannabis ) Cannabigerovarin ( cannabis ) Cannabinol ( cannabis ) Capsazepine DCDPC DHEA DHEA - S Flufenamic acid GRC - 6211 HC - 067047 Lanthanum Meclofenamic acid N - ( p - amylcinnamoyl ) anthranilic acid NGD - 8243 Niflumic acid Pregnenolone sulfate RN - 1734 RN - 9893 Ruthenium red SB - 705498 Tolfenamic acid See also : Receptor / signaling modulators Ion channel modulators LCCN : sh85006365 GND : 4142846 - 8 NDL : 00575686 Retrieved from `` https://en.wikipedia.org/w/index.php?title=Arachidonic_acid&oldid=807842466 '' Categories : Fatty acids Alkenoic acids Hidden categories : Articles with changed DrugBank identifier ECHA InfoCard ID from Wikidata Articles with changed KEGG identifier Articles with changed InChI identifier Chembox having DSD data Articles containing unverified chemical infoboxes All articles with unsourced statements Articles with unsourced statements from May 2017 Pages using div col with small parameter Wikipedia articles with LCCN identifiers Wikipedia articles with GND identifiers Talk Contents About Wikipedia Беларуская Bosanski Català Čeština Dansk Deutsch Español Euskara فارسی Français Gaeilge Galego 한국어 Հայերեն Italiano עברית Қазақша Latviešu Magyar Nederlands 日本 語 Polski Português Română Русский Slovenščina Српски / srpski Srpskohrvatski / српскохрватски Suomi Svenska Українська 中文 Edit links This page was last edited on 30 October 2017, at 12 : 27. 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Question: where is arachidonic acid stored in the body
Answer: brain