A9673

Arachidonic acid

from Porcine liver, ≥99% (GC), liquid

• Synonim(y): cis,cis,cis,cis-5,8,11,14-Eicosatetraenoic acid, Eicosa-5Z,8Z,11Z,14Z-tetraenoic acid, Immunocytophyte
• Wzór liniowy: CH₃(CH₂)₄(CH=CHCH₂)₄CH₂CH₂CO₂H
• Numer CAS: 506-32-1
• Masa cząsteczkowa: 304.47
• EC Number: 208-033-4
• UNSPSC Code: 12352211
• PubChem Substance ID: 24891487
• Beilstein/REAXYS Number: 1713889
• MDL number: MFCD00004417

Właściwości

• biological source: Porcine liver
• assay: ≥99% (GC)
• form: liquid
• color: clear colorless to very faintly 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 (lit.)(lit.)
• density: 0.922 g/mL at 25 °C (lit.)
• application(s): food and beverages
• functional group: carboxylic acid
• shipped in: dry ice
• storage temp.: −20°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

Opis

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 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.

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

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Informacja o środkach bezpieczeństwa

• pictograms: GHS07
• signalword: Warning
• hcodes: H315,H319
• pcodes: P264 - P280 - P302 + P352 - P305 + P351 + P338 - P332 + P313 - P337 + P313
• Hazard Classifications: Eye Irrit. 2 - Skin Irrit. 2
• Klasa składowania: 10 - Combustible liquids
• wgk: WGK 3
• flash_point_f: 235.4 °F - closed cup
• flash_point_c: 113 °C - closed cup
• ppe: Eyeshields, Faceshields, Gloves, multi-purpose combination respirator cartridge (US)