10929
Arachidonic acid
puriss., ≥98.5% (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:
Molecular Weight:
304.47
EC Number:
208-033-4
UNSPSC Code:
12352211
MDL number:
Beilstein/REAXYS Number:
1713889
grade
puriss.
assay
≥98.5% (GC)
refractive index
n20/D 1.4872 (lit.)
bp
169-171 °C/0.15 mmHg (lit.)
mp
−49 °C (lit.)
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
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 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) .
Packaging
Bottomless glass bottle. Contents are inside inserted fused cone.
Other Notes
Precursor of many potent biological mediators such as prostaglandins, thromboxanes, leukotrienes. Role of arachidonic acid in the metabolism of platelet-activating factor (PAF)
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Alkylacetylglycerols versus lyso-PAF as precursors in PAF biosynthesis and the role of arachidonic acid in PAF metabolism.
F Snyder et al.
Pharmacological research communications, 18 Suppl, 33-41 (1986-08-01)
Joy Hsu et al.
The Journal of allergy and clinical immunology, 131(4), 977-993 (2013-04-02)
The cause of chronic rhinosinusitis (CRS) remains unclear. Study of the genetic susceptibility to CRS might be a valuable strategy to understand the pathogenesis of this burdensome disorder. The purpose of this review is to critically evaluate the current literature
Luis Gil-de-Gómez et al.
Journal of immunology (Baltimore, Md. : 1950), 190(10), 5169-5177 (2013-04-10)
Activation of macrophages with stimuli of the innate immune response results in the intense remodeling of arachidonate-containing phospholipids, leading to the mobilization of large quantities of this fatty acid for conversion into biologically active eicosanoids. As a consequence of this
Global Trade Item Number
| SKU | GTIN |
|---|---|
| 298190-50G | 04061826657119 |
| 429406-25G | 04061838139672 |
| 429406-5G | 04061832105628 |