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A3611 Sigma-Aldrich

Arachidonic acid

from non-animal source, ≥98.5% (GC)

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

  • CAS Number 506-32-1

  • Linear Formula CH3(CH2)4(CH=CHCH2)4CH2CH2CO2H

  • Molecular Weight 304.47

  •  Beilstein/REAXYS Number 1713889

  •  EC Number 208-033-4

  •  MDL number MFCD00004417

  •  PubChem Substance ID 329770839

  •  NACRES NA.25

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Properties

Related Categories Cell Biology, Cell Culture, Functional Foods, Lipids, Lipids and Lipid Carriers,
Quality Level   300
biological source   non-animal source
assay   ≥98.5% (GC)
form   liquid
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.)
functional group   carboxylic acid
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

Description

Packaging

1 g in ampule

10, 100 mg in ampule

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

Safety & Documentation

Safety Information

RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
Flash Point(F) 
235.4 °F - closed cup
Flash Point(C) 
113 °C - closed cup

Documents

Certificate of Analysis (COA)

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Certificate of Origin (COO)

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Protocols & Articles

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Peer-Reviewed Papers
15

References

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