23401

Arachidonic acid

analytical standard

• Synonym(s): cis,cis,cis,cis-5,8,11,14-Eicosatetraenoic acid, Eicosa-5Z,8Z,11Z,14Z-tetraenoic acid, Immunocytophyte
• Linear Formula: CH₃(CH₂)₄(CH=CHCH₂)₄CH₂CH₂CO₂H
• CAS Number: 506-32-1
• Molecular Weight: 304.47
• Beilstein: 1713889
• EC Number: 208-033-4
• MDL number: MFCD00004417
• PubChem Substance ID: 329752420
• NACRES: NA.24

Properties

• biological source: synthetic
• Quality Level: 100
• grade: analytical standard
• assay: ≥97.0% (GC)
• form: liquid
• shelf life: limited shelf life, expiry date on the label
• refractive index: n20/D 1.4872 (lit.)
• bp: 169-171 °C/0.15 mmHg (lit.)
• mp: −49 °C (lit.)
• density: 0.922 g/mL at 25 °C (lit.)
• application(s): food and beverages
• format: neat
• functional group: carboxylic acid
• storage temp.: 2-8°C
• SMILES string: OC(CCC/C=C\C/C=C\C/C=C\C/C=C\CCCCC)=O
• InChI: 1S/C20H32O2/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)/b7-6-,10-9-,13-12-,16-15-
• InChI key: YZXBAPSDXZZRGB-DOFZRALJSA-N

Description

Packaging

50 mg

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) .

Safety Information

• Storage Class Code: 10 - Combustible liquids
• WGK: WGK 3
• Flash Point(F): 235.4 °F - closed cup
• Flash Point(C): 113 °C - closed cup