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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

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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

RIDADR 
NONH for all modes of transport
WGK Germany 
3
RTECS 
CE6675000
Flash Point(F) 
235.4 °F
Flash Point(C) 
113 °C

Documents

Certificate of Analysis

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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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