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08-SEPTEMBER-2008 09:13:22 - Arachidonic acid Arachidonic acid IUPAC name all-cis-5,8,11,14-eicosatetraenoic acid Identifiers CAS number 506-32-1 SMILES CCCCCC=CCC=CCC=CCC=CCCCC=OO Properties Molecular formula C20H32O2. Molar mass 304.5 g/mol Melting point -49.5 °C Boiling point °C dec. Except where noted otherwise, data are given for materials in their standard state at 25 °C, 100 kPa Infobox references Arachidonic acid AA, sometimes ARA is an omega-6 fatty acid 20:4ω-6. It is the counterpart to the saturated arachidic acid found in peanut oil, L. arachis - peanut.1 Contents 1 Chemistry 2 Biology 3 Synthesis and cascade 4 Essential fatty acid 5 See also 6 References 7 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 that is present in the phospholipids especially phosphatidylethanolamine, phosphatidylcholine and phosphatidylinositides of membranes of the body's cells, and is abundant in the brain. It is also involved in cellular signaling as a second messenger. It is the source of several other molecules with specific roles, as described in the next section. Synthesis and cascade Eicosanoid synthesis. Eicosanoid synthesis. Arachidonic acid is freed from phospholipid molecule by the enzyme phospholipase A2, which cleaves off the fatty acid. Arachidonic acid is a precursor in the production of eicosanoids: the enzymes cyclooxygenase and peroxidase lead to Prostaglandin H2, which in turn is used to produce the prostaglandins, prostacyclin, and thromboxanes. the enzyme 5-lipoxygenase leads to 5-HPETE, which in turn is used to produce the leukotrienes. arachidonic acid is also used in the biosynthesis of anandamide. The production of these derivatives and their action in the body are collectively known as the arachidonic acid cascade; see essential fatty acid interactions for more details. Essential fatty acid Main article: Essential fatty acid#Essentiality Arachidonic acid in the human body comes from dietary animal sources-meat, eggs, dairy-or is synthesized from linoleic acid. Arachidonic acid in the human body comes from dietary animal sources-meat, eggs, dairy-or is synthesized from linoleic acid. Arachidonic acid is one of the essential fatty acids 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 diet. Since little or no arachidonic acid is found in plants, such animals are obligate carnivores; the cat is a common example.23 See also Polyunsaturated fat Polyunsaturated fatty acid Aspirin - inhibits cyclooxygenase enzyme to prevent the conversion of arachidonic acid to other signal molecules References ^ Dorland's Medical Dictionary - 'A'. Retrieved on 2007-01-12. ^ MacDonald M, Rogers Q, Morris J 1984. Nutrition of the domestic cat, a mammalian carnivore. Annu Rev Nutr 4: 521-62. doi:10.1146/annurev.nu.04.070184.002513. PMID 6380542. Retrieved on 2007-02-09. ^ Rivers J, Sinclair A, Crawford M 1975. Inability of the cat to desaturate essential fatty acids. Nature 258 5531: 171-3. doi:10.1038/258171a0. PMID 1186900. External links Arachidonic Acid at acnp.org MeSH Arachidonic+Acid v d e Autacoids, unsaturated fatty acids: Eicosanoids Prostanoids Prostaglandins - Thromboxanes A2, B2 Leukotrienes A4 - B4 - Slow reacting substance of anaphylaxis C4, D4, E4 Other Arachidonic acids - Eicosapentaenoic acid - Lipoxins v d e Lipids: fatty acids Saturated Butyric Hexanoic Caprylic Decanoic Lauric Myristic Palmitic Stearic Arachidic Behenic Lignoceric n-3 Unsaturated α-Linolenic Stearidonic Eicosapentaenoic Docosahexaenoic n-6 Unsaturated Linoleic γ-Linolenic Dihomo-γ-linolenic Arachidonic n-9 Unsaturated Oleic Erucic Nervonic Retrieved from http://en..org/wiki/Arachidonic_acid Categories: Fatty acids Views Article Discussion this page History Personal tools Log in / create account Navigation Main page Contents Featured content Current events Random article Search Go Search Interaction Community portal Recent changes Contact Donate to Help Toolbox What links here Related changes Upload file Special pages Printable version Permanent link Cite this page Languages Deutsch Español Ù?ارسی Français עברית Italiano LatvieÅ¡u Nederlands 日本語 Polski Português РуÑ?Ñ?кий SlovenÅ¡Ä?ina Suomi This page was last modified on 28 July 2008, at 11:53
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