23401

Arachidonic acid

analytical standard

• 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
• UNSPSC Code: 85151701
• NACRES: NA.24
• PubChem Substance ID: 329752420
• EC Number: 208-033-4
• Beilstein/REAXYS Number: 1713889
• MDL number: MFCD00004417

Właściwości

• biological source: synthetic
• Quality Segment: 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

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

• Piktogramy: GHS07
• Słowo ostrzegawcze: Warning
• Kody zagrożeń: H315,H319
• Ostrzeżenia: P264 - P280 - P302 + P352 - P305 + P351 + P338 - P332 + P313 - P337 + P313
• Hazard Classifications: Eye Irrit. 2 - Skin Irrit. 2
• Klasa składowania: 10 - Combustible liquids
• Co się dzieje?: WGK 3
• Temperatura zapłonu (°F): 235.4 °F - closed cup
• Temperatura zapłonu (°C): 113 °C - closed cup