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A3925 Sigma

Arachidonic acid

from porcine liver, ≥85% (capillary GC), liquid

Synonym: cis,cis,cis,cis-5,8,11,14-Eicosatetraenoic acid, Eicosa-5Z,8Z,11Z,14Z-tetraenoic acid, Immunocytophyte

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Properties

Related Categories Arachidonic Acid, Arachidonic Acid Cascade, Biochemicals and Reagents, Cell Biology, Cell Signaling and Neuroscience,
biological source   from porcine liver
InChI Key   YZXBAPSDXZZRGB-DOFZRALJSA-N
assay   ≥85% (capillary GC)
form   liquid
color   colorless to light yellow
refractive index   n20/D 1.4872(lit.)
bp   169-171 °C/0.15 mmHg(lit.)
mp   −49 °C(lit.)
solubility   ethanol: ≥10 mg/mL
density   0.922 g/mL at 25 °C(lit.)
storage temp.   −20°C

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 a 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.

Arachidonic acid stimulates adhesion of MDA-MB-435 human metastatic cancer cells to extracellular matrix molecules (collagen IV and vitronectin) .

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Safety & Documentation

Safety Information

RIDADR 
NONH for all modes of transport
WGK Germany 
3
RTECS 
CE6675000
Flash Point(F) 
235.4 °F
Flash Point(C) 
113 °C
Protocols & Articles
Peer-Reviewed Papers
15

References

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