A8798

Arachidonic acid sodium salt

from Porcine liver, ≥99% (capillary GC), waxy solid

• Synonym(s): 5,8,11,14-Eicosatetraenoic acid, Eicosa-5Z,8Z,11Z,14Z-tetraenoic acid, Sodium arachidonate, cis,cis,cis,cis-5,8,11,14-Eicosatetraenoic acid sodium salt, 20:4
• Empirical Formula (Hill Notation): C₂₀H₃₁O₂Na
• CAS Number: 6610-25-9
• Molecular Weight: 326.45
• MDL number: MFCD00065458
• PubChem Substance ID: 24891365

Properties

• biological source: 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
• SMILES string: [Na+].CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC([O-])=O
• InChI: 1S/C20H32O2.Na/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22;/h6-7,9-10,12-13,15-16H,2-5,8,11,14,17-19H2,1H3,(H,21,22);/q;+1/p-1/b7-6-,10-9-,13-12-,16-15-;
• InChI key: DDMGAAYEUNWXSI-XVSDJDOKSA-M

Description

General description

Arachidonic acid (AA) is a polyunsaturated ω⁶ fatty acid constituent of the phospholipids of cell membranes. Structurally, it is a 20-carbon chain that contains four cis double bonds, which allow the free acid form of AA to be an insoluble oil; this can be converted to the water-soluble sodium salt form within the normal physiological pH range. AA is metabolized by multiple enzymes to yield various metabolites; 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.

Application

Arachidonic acid is used in assays to measure activity of oxidizing enzymes, such as cyclooxygenase, as well as in assays to determine platelet inhibition in whole blood. AA has been demonstrated to bind to the α subunit of G protein and inhibit the activity of Ras GTPase-activating proteins (GAPs), to have a role in the development and progression of prostate cancer, and to enhance formation of lipid bodies in human mast cells.

Biochem/physiol Actions

Released arachidonic acid (AA) reacts with molecular oxygen nonenzymatically, through oxidative stress, and enzymatically through the action of oxygenase enzymes. AA is oxidized 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. 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.

Safety Information

• Storage Class Code: 13 - Non Combustible Solids
• WGK: WGK 3
• Flash Point(F): 235.4 °F - closed cup
• Flash Point(C): 113 °C - closed cup
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves