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10931 Sigma-Aldrich

Arachidonic acid

>95.0% (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 57646859

  •  NACRES NA.25

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Properties

Related Categories Arachidonic Acid, Arachidonic Acid Cascade, Biochemicals and Reagents, Building Blocks, C13 to C42+,
Quality Level   100
biological source   fungus
assay   >95.0% (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

Application

Arachidonic acid has been used:
• in calibration curve generation in Raman spectroscopy and atomic force microscopy (AFM) in normal and breast cancer samples
• as a polyunsaturated fatty acid supplement to the reconstituted synthetic bile (RSB) in drug resistance analysis
• for the activation of mechanistic target of rapamycin 1 (mTOR1) and mTOR2

Packaging

1 g in glass bottle

250 mg in glass bottle

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) .

Safety & Documentation

Safety Information

Symbol 
GHS07  GHS07
Signal word 
Warning
Target organs 
Respiratory system
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
RTECS 
CE6675000
Flash Point(F) 
235.4 °F - closed cup
Flash Point(C) 
113 °C - closed cup
Protocols & Articles

Articles

FAMLS Online Plate Map

FAMLS compounds are conveniently provided at 5µg per well, enough for multiple injections. These are high purity (>95%) compounds supplied in an economical, ready to use format. Compounds are arrange...
Keywords: Metabolites

Peer-Reviewed Papers
15

References

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