10931

Arachidonic acid

>95.0% (GC)

• Sinônimo(s): cis,cis,cis,cis-5,8,11,14-Eicosatetraenoic acid, Eicosa-5Z,8Z,11Z,14Z-tetraenoic acid, Immunocytophyte
• Fórmula linear: CH₃(CH₂)₄(CH=CHCH₂)₄CH₂CH₂CO₂H
• Número CAS: 506-32-1
• Peso molecular: 304.47
• Beilstein: 1713889
• Número CE: 208-033-4
• Número MDL: MFCD00004417
• Código UNSPSC: 12352211
• ID de substância PubChem: 57646859
• NACRES: NA.25

Propriedades

• fonte biológica: fungus
• Ensaio: >95.0% (GC)
• Formulário: liquid
• índice de refração: n20/D 1.4872 (lit.)
• p.e.: 169-171 °C/0.15 mmHg (lit.)
• pf: −49 °C (lit.)
• densidade: 0.922 g/mL at 25 °C (lit.)
• grupo funcional: carboxylic acid
• tipo de lipídio: omega FAs
• Condições de expedição: dry ice
• temperatura de armazenamento: −20°C
• cadeia de caracteres SMILES: 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-
• chave InChI: YZXBAPSDXZZRGB-DOFZRALJSA-N

Descrição

Aplicação

Arachidonic acid has been used:

• in calibration curve generation in Raman spectroscopy and atomic force microscopy (AFM) in normal and breast cancer samples[1]
• as a polyunsaturated fatty acid supplement to the reconstituted synthetic bile (RSB) in drug resistance analysis[2]
• for the activation of mechanistic target of rapamycin 1 (mTOR1) and mTOR2[3]

Ações bioquímicas/fisiológicas

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) .

Informações de segurança

• Pictogramas: GHS07
• Palavra indicadora: Warning
• Frases de perigo: H315,H319
• Declarações de precaução: P264 - P280 - P302 + P352 - P305 + P351 + P338 - P332 + P313 - P337 + P313
• Classificações de perigo: Eye Irrit. 2 - Skin Irrit. 2
• Código de classe de armazenamento: 10 - Combustible liquids
• Classe de risco de água (WGK): WGK 3
• Ponto de fulgor (°F): 235.4 °F - closed cup
• Ponto de fulgor (°C): 113 °C - closed cup
• Equipamento de proteção individual: Eyeshields, Faceshields, Gloves, multi-purpose combination respirator cartridge (US)