Description
Biochem/physiol Actions Arachidonic acid （AA） is an unsaturated ω6 fatty acid constituent of the phospholipids of cell membranes. Phospholipase A2 releases AA from the membrane phospholipids in response to inflammation. AA is subsequently metabolized to prostaglandins and thromboxanes by at least two cyclooxygenase （COX） isoforms, to leukotrienes and lipoxins by lipoxygenases, and to epoxyeicosatrienoic acids via cytochrome p450-catalyzed metabolism. AA and its metabolites play important roles in a variety of biological processes, including signal transduction, smooth muscle contraction, chemotaxis, cell proliferation and differentiation, and apoptosis. AA has been demonstrated to bind to the α subunit of G protein and inhibit the activity of Ras GTPase-activating proteins （GAPs）. Cellular uptake of AA is energy dependent and involves protein-facilitated transport across the plasma membrane.
Caution The sodium salts of arachidonic acid are very sensitive to oxidation and will turn yellow and deteriorate rapidly in air. They are packaged under vacuum in sealed ampules. Once opened the product must be used quickly or transferred into an inert atmosphere （dry argon） as soon as possible.

Properties
biological source from porcine liver
assay ≥99% （capillary GC）
form waxy solid
color white to off-white
solubility methanol: 50 mg/mL, clear, colorless to faintly yellow
shipped in dry ice
storage temp. −20°C

Safety
Personal Protective Equipment Eyeshields, full-face particle respirator type N100 （US）, Gloves, respirator cartridge type N100 （US）, type P1 （EN143） respirator filter, type P3 （EN 143） respirator cartridges
Risk Statements 19
WGK Germany 3
RTECS JX3874000
Flash Point（F） 235.4 °F
Flash Point（C） 113 °C

References
reference Ghosh, J., and Myers, C.E., Inhibition of arachidonate 5-lipoxygenase triggers massive apoptosis in human prostate cancer cells. Proc. Natl. Acad. Sci. U. S. A. 95, 13182-13187, （1998）
  Prigge, S.T., et al., Structure and mechanism of lipoxygenases. Biochimie 79, 629-636, （1997）
  Karim, S., et al., Cyclooxygenase-1 and -2 of endothelial cells utilize exogenous or endogenous arachidonic acid for transcellular production of thromboxane. J. Biol. Chem. 271, 12042-12048, （1996）
  Krischer, S.M., et al., Transport of arachidonic acid across the neutrophil plasma membrane via a protein-facilitated mechanism. Biochemistry 37, 12884-12891, （1998）
  Makita, K., et al., Cytochrome P450, the arachidonic acid cascade, and hypertension: new vistas for an old enzyme system. FASEB J. 10, 1456-1463, （1996）
  Kim, B.C, and Kim, J.H.,, Nuclear signalling by Rac GTPase: essential role of phospholipase A2. Biochem. J. 326, 333-337, （1997）
  Seegers, J.C., et al., Comparative anti-mitotic effects of lithium γ-linolenate, γ-linolenic acid and arachidonic acid, on transformed and embryonic cells. Prostaglandins Leukot. Essent. Fatty Acids 59, 285-291, （1998）
  Williams, J.R., et al., Apoptosis in human primary brain tumours: actions of arachidonic acid. Prostaglandins Leukot. Essent. Fatty Acids 58, 193-200, （1998）
  Hallak, H., et al., Covalent binding of arachidonate to G protein alpha subunits of human plaets. J. Biol. Chem. 269, 4713-4716, （1994）
  Sermon, B.A., et al., Mechanism of inhibition by arachidonic acid of the catalytic activity of Ras GTPase-activating proteins. J. Biol. Chem. 271, 1566-1572, （1996）

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