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A3555

Sigma-Aldrich

Arachidonic acid

from Porcine liver, BioReagent, suitable for cell culture, ≥99% (GC)

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:
12352200
ID PubChem:
24890784

Origine biologica

Porcine liver

Nome Commerciale

BioReagent

Saggio

≥99% (GC)

Stato

liquid

tecniche

cell culture | mammalian: suitable

Colore

clear colorless to very faintly yellow

Indice di rifrazione

n20/D 1.4872 (lit.)

P. ebollizione

169-171 °C/0.15 mmHg (lit.)

Punto di fusione

−49 °C (lit.)

Solubilità

absolute ethanol: 10 mg/mL

Densità

0.922 g/mL at 25 °C (lit.)

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 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) .

Confezionamento

Sealed ampule.

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

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Certificati d'analisi (COA)

Lot/Batch Number
SLBK8783V
SLBH2583V
SLBD9828V
SLBB9784V
071M1333V

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Zhuoming Liu et al.
The Journal of biological chemistry, 281(23), 16043-16051 (2006-04-15)
Dbs was identified in a cDNA-based expression screen for sequences that can cause malignant growth when expressed in murine fibroblasts. In previous studies we have shown that Dbs is a Rho-specific guanine nucleotide exchange factor that can activate RhoA and/or
Ninna Struck Rossen et al.
PloS one, 6(9), e25196-e25196 (2011-10-04)
Cell adhesion and migration are essential for the evolution, organization, and repair of living organisms. An example of a combination of these processes is the formation of new blood vessels (angiogenesis), which is mediated by a directed migration and adhesion
Song Xu et al.
Journal of virology, 86(23), 13025-13037 (2012-09-28)
Similar to other positive-sense, single-stranded RNA viruses, hepatitis C virus (HCV) replicates its genome in a remodeled intracellular membranous structure known as the membranous web (MW). To date, the process of MW formation remains unclear. It is generally acknowledged that
Akinobu Hayashi et al.
Oncology letters, 8(4), 1513-1518 (2014-09-10)
Transforming growth factor β1 (TGFβ1) regulates a variety of cellular functions, including cell growth, apoptosis and differentiation. The aim of the current study was to investigate the alterations of phenotypic events in the long-term exposure of prostate cancer (PCa) cells
Donghui Liu et al.
American journal of physiology. Cell physiology, 301(3), C739-C748 (2011-07-08)
High-density lipoprotein (HDL) can induce cyclooxygenase-2 (COX-2) expression and prostacyclin I-2 (PGI-2) release in endothelial cells to exert multiple antiatherogenic functions. This effect has been attributed mainly to the role of sphingosine-1-phosphate (S1P) integrated in HDL. However, whether apolipoprotein A-I
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