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A3555

Sigma-Aldrich

Arachidonic acid

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

Synonym(s):

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

Linear Formula:
CH3(CH2)4(CH=CHCH2)4CH2CH2CO2H
CAS Number:
506-32-1
Molecular Weight:
304.47
Beilstein/REAXYS Number:
1713889
EC Number:
208-033-4
MDL number:
MFCD00004417
UNSPSC Code:
12352200
PubChem Substance ID:
24890784

biological source

Porcine liver

product line

BioReagent

assay

≥99% (GC)

form

liquid

technique(s)

cell culture | mammalian: suitable

color

clear colorless to very faintly yellow

refractive index

n20/D 1.4872 (lit.)

bp

169-171 °C/0.15 mmHg (lit.)

mp

−49 °C (lit.)

solubility

absolute ethanol: 10 mg/mL

density

0.922 g/mL at 25 °C (lit.)

shipped in

dry ice

storage temp.

−20°C

SMILES string

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-

InChI key

YZXBAPSDXZZRGB-DOFZRALJSA-N

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Biochem/physiol Actions

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) .

Packaging

Sealed ampule.

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H315,H319

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2

Storage Class

10 - Combustible liquids

wgk_germany

WGK 3

flash_point_f

235.4 °F - closed cup

flash_point_c

113 °C - closed cup

Certificates of Analysis (COA)

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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
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
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
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
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
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