Arachidonic acid, >95.0% (GC)

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

CAS Number: 506-32-1

Formula: C20H32O2

Formula Weight: 304.47

Linear Formula: CH3(CH2)4(CH=CHCH2)4CH2CH2CO2H

MDL No.: MFCD00004417

Purity: >95.0% (GC)

Boiling Point: 169-171 C/0.15 mmHg(lit.)

Melting Point: -49 C (lit.)

Density: 0.922 g/mL at 25 C(lit.)

Refractive Index: n20/D 1.4872(lit.)

Storage: -20C

Beilstein Registry Number: 1713889

EC Number: 208-033-4

UNSPSC Code: 12352211

Biochem/physiol Actions: Arachidonic acid (AA) is an unsaturated omega6 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.

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