Arachidonic acid 

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.

Sealed ampule

from porcine liver

~99% (capillary GC)

oil

clear

n20/D 1.4872(lit.)

169-171 °C/0.15 mmHg(lit.)

−49 °C(lit.)

ethanol: ≥10 mg/mL

0.922 g/mL at 25 °C(lit.)

dry ice

−20°C

Ghosh, J., and Myers, C.E., Inhibition of arachidonate 5-lipoxygenase triggers massive apoptosis in human prostate cancer cells. Proc. Natl. Acad. Sci. USA 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)

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)

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)

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)

Hallak, H., et al., Covalent binding of arachidonate to G protein alpha subunits of human platelets. J. Biol. Chem. 269, 4713-4716, (1994)

Williams, J.R., et al., Apoptosis in human primary brain tumours: actions of arachidonic acid. Prostaglandins Leukot. Essent. Fatty Acids 58, 193-200, (1998)

Kim, B.C, and Kim, J.H.,, Nuclear signalling by Rac GTPase: essential role of phospholipase A2. Biochem. J. 326, 333-337, (1997)

Krischer, S.M., et al., Transport of arachidonic acid across the neutrophil plasma membrane via a protein-facilitated mechanism. Biochemistry 37, 12884-12891, (1998)

Merck 13,769

Beil. 2,H,469

Aldrich MSDS 1, 135:A / Corp MSDS 1 (1), 298:B / FT-IR 2 (1), 786:D / FT-IR 1 (1), 502:C / NMR-Reference 2 (1), 438:A / RegBook 1 (1), 551:K / Sax 6, 311 / Sigma FT-IR 1 (1), 1361:A / Structure Index 1, 78:B:5

3

CE6675000

235 °F

113 °C