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A9673

Sigma-Aldrich

Arachidonic acid

from Porcine liver, ≥99% (GC), liquid

Sinonimo/i:

cis,cis,cis,cis-5,8,11,14-Eicosatetraenoic acid, Eicosa-5Z,8Z,11Z,14Z-tetraenoic acid, Immunocytophyte

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About This Item

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:
24891487

Origine biologica

Porcine liver

Saggio

≥99% (GC)

Forma fisica

liquid

Colore

clear colorless to very faintly yellow

Indice di rifrazione

n20/D 1.4872 (lit.)

P. eboll.

169-171 °C/0.15 mmHg (lit.)

Punto di fusione

−49 °C (lit.)

Solubilità

ethanol: ≥10 mg/mL (lit.)(lit.)

Densità

0.922 g/mL at 25 °C (lit.)

applicazioni

food and beverages

Gruppo funzionale

carboxylic acid

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-
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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) .

Pittogrammi

Exclamation mark
GHS07

Avvertenze

Warning

Indicazioni di pericolo

H315,H319

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)

Certificati d'analisi (COA)

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Channels (Austin, Tex.), 7(2), 74-84 (2013-01-22)
Polyunsaturated fatty acids such as arachidonic acid (AA) exhibit inhibitory modulation of Kv4 potassium channels. Molecular docking approaches using a Kv4.2 homology model predicted a membrane-embedded binding pocket for AA comprised of the S4-S5 linker on one subunit and several
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