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Arachidonic Acid, MP Biomedicals™

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Description

Arachidonic acid is an essential fatty acid, and a precursor in the biosynthesis of prostaglandins, thromboxanes, and leukotrienes. It occurs in liver, brain, glandular organs, and depot fats of animals, in small amounts in human depot fats, and is a cons

Arachidonic acid (AA) is an unsaturated ω-6 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). Arachidonic acid plays a key role in cellular regulation and is controlled through multiple interconnected pathways. Changes in arachidonic acid levels correspond to the synthesis of eicosanoids resulting from receptor-stimulated lipid hydrolysis.It activates protein kinase C. Arachidonic acid serves as a precursor to numerous eicosanoids as well as other bioactive molecules.

TRUSTED_SUSTAINABILITY

Chemical Identifiers

CAS 506-32-1
Molecular Formula C20H32O2
Molecular Weight (g/mol) 304.474
InChI Key YZXBAPSDXZZRGB-DOFZRALJSA-N
Synonym arachidonic acid, arachidonate, immunocytophyte, all-z-5,8,11,14-eicosatetraenoic acid, 5z,8z,11z,14z-icosa-5,8,11,14-tetraenoic acid, cis-5,8,11,14-eicosatetraenoic acid, 5,8,11,14-eicosatetraenoic acid, all-z, all-cis-5,8,11,14-eicosatetraenoic acid, unii-27yg812j1i, 5z,8z,11z,14z-eicosatetraenoic acid
PubChem CID 444899
ChEBI CHEBI:15843
IUPAC Name (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoic acid
SMILES CCCCCC=CCC=CCC=CCC=CCCCC(=O)O

Specifications

Melting Point -49°C (literature)
Density 0.922g/mL (Lit.)
Boiling Point 170°C (0.2 mmHg (literature))
Refractive Index n20/D 1.4872 (Lit.)
Quantity 1 g
Formula Weight 304.5
Percent Purity >98%
Physical Form Liquid

Safety and Handling

Recommended Storage Store at 0°C, desiccate, protect from light, under nitrogen.
WARNING: Reproductive Harm - www.P65Warnings.ca.gov
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