10931

Arachidonic acid

>95.0% (GC)

• Sinonimo/i: cis,cis,cis,cis-5,8,11,14-Eicosatetraenoic acid, Eicosa-5Z,8Z,11Z,14Z-tetraenoic acid, Immunocytophyte
• Formula condensata: CH₃(CH₂)₄(CH=CHCH₂)₄CH₂CH₂CO₂H
• Numero CAS: 506-32-1
• Peso molecolare: 304.47
• Beilstein: 1713889
• Numero CE: 208-033-4
• Numero MDL: MFCD00004417
• Codice UNSPSC: 12352211
• ID PubChem: 57646859
• NACRES: NA.25

Proprietà

• Origine biologica: fungus
• Saggio: >95.0% (GC)
• Forma fisica: liquid
• Indice di rifrazione: n20/D 1.4872 (lit.)
• P. eboll.: 169-171 °C/0.15 mmHg (lit.)
• Punto di fusione: −49 °C (lit.)
• Densità: 0.922 g/mL at 25 °C (lit.)
• Gruppo funzionale: carboxylic acid
• Tipo di lipide: omega FAs
• Condizioni di spedizione: dry ice
• Temperatura di conservazione: −20°C
• Stringa SMILE: 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-; YZXBAPSDXZZRGB-DOFZRALJSA-N

Descrizione

Applicazioni

Arachidonic acid has been used:

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

Azioni biochim/fisiol

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) .

Informazioni sulla sicurezza

• Pittogrammi: GHS07
• Avvertenze: Warning
• Indicazioni di pericolo: H315,H319
• Consigli di prudenza: P264 - P280 - P302 + P352 - P305 + P351 + P338 - P332 + P313 - P337 + P313
• Classi di pericolo: Eye Irrit. 2 - Skin Irrit. 2
• Codice della classe di stoccaggio: 10 - Combustible liquids
• Classe di pericolosità dell'acqua (WGK): WGK 3
• Punto d’infiammabilità (°F): 235.4 °F - closed cup
• Punto d’infiammabilità (°C): 113 °C - closed cup
• Dispositivi di protezione individuale: Eyeshields, Faceshields, Gloves, multi-purpose combination respirator cartridge (US)