10931

Arachidonic acid

>95.0% (GC)

• 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
• Beilstein: 1713889
• Numer WE: 208-033-4
• Numer MDL: MFCD00004417
• Kod UNSPSC: 12352211
• Identyfikator substancji w PubChem: 57646859
• NACRES: NA.25

Właściwości

• pochodzenie biologiczne: fungus
• Próba: >95.0% (GC)
• Postać: liquid
• współczynnik refrakcji: n20/D 1.4872 (lit.)
• tw: 169-171 °C/0.15 mmHg (lit.)
• mp: −49 °C (lit.)
• gęstość: 0.922 g/mL at 25 °C (lit.)
• grupa funkcyjna: carboxylic acid
• typ lipidu: omega FAs
• Warunki transportu: dry ice
• temp. przechowywania: −20°C
• ciąg 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-
• Klucz InChI: YZXBAPSDXZZRGB-DOFZRALJSA-N

Opis

Zastosowanie

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

Działania biochem./fizjol.

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) .

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Informacja o środkach bezpieczeństwa

• Piktogramy: GHS07
• Hasło ostrzegawcze: Warning
• Zwroty wskazujące rodzaj zagrożenia: H315,H319
• Zwroty wskazujące środki ostrożności: P264 - P280 - P302 + P352 - P305 + P351 + P338 - P332 + P313 - P337 + P313
• Klasyfikacja zagrożeń: Eye Irrit. 2 - Skin Irrit. 2
• Kod klasy składowania: 10 - Combustible liquids
• Klasa zagrożenia wodnego (WGK): WGK 3
• Temperatura zapłonu (°F): 235.4 °F - closed cup
• Temperatura zapłonu (°C): 113 °C - closed cup
• Środki ochrony indywidualnej: Eyeshields, Faceshields, Gloves, multi-purpose combination respirator cartridge (US)