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A36883 Sigma-Aldrich

Aurintricarboxylic acid ammonium salt

ACS reagent

Synonym: ATA, Aluminon, Ammonium aurintricarboxylate

  • CAS Number 569-58-4

  • Linear Formula C22H14O9 · 3NH3

  • Molecular Weight 473.43

  •  Colour Index Number 43810

  •  Beilstein/REAXYS Number 3900820

  •  EC Number 209-319-1

  •  MDL number MFCD00040925

  •  PubChem Substance ID 24890803

  •  NACRES NA.47

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Properties

Related Categories Biochemicals and Reagents, Building Blocks, Carbonyl Compounds, Carboxylic Acid Salts, Chemical Synthesis,
Quality Level   200
biological source   synthetic
grade   ACS reagent
form   powder or crystals
impurities   ≤0.1% insolubles
ign. residue   ≤0.2%
mp   220-225 °C (dec.) (lit.)
solubility   water: soluble 100 mg/mL
λmax   450 nm
  522 nm (2nd)
SMILES string   N.N.N.OC(=O)c1cc(ccc1O)\C(c2ccc(O)c(c2)C(O)=O)=C3/C=CC(=O)C(=C3)C(O)=O
InChI   1S/C22H14O9.3H3N/c23-16-4-1-10(7-13(16)20(26)27)19(11-2-5-17(24)14(8-11)21(28)29)12-3-6-18(25)15(9-12)22(30)31;;;/h1-9,23-24H,(H,26,27)(H,28,29)(H,30,31);3*1H3
InChI key   AIPNSHNRCQOTRI-UHFFFAOYSA-N

Description

Packaging

25, 100 g in glass bottle

Application

Reagent for aluminum

Biochem/physiol Actions

Aurintricarboxylic acid readily polymerizes in aqueous solution, forming a stable free radical that inhibits protein-nucleic acid interactions. It is a potent inhibitor of ribonuclease and topoisomerase II by preventing the binding of the nucleic acid to the enzyme. It stimulates tyrosine phosphorylation processes including the Jak2/STAT5 pathway in NB2 lymphoma cells, ErbB4 in neuroblastoma cells, and MAP kinases, Shc proteins, phosphatidylinositide 3-kinase and phospholipase C in PC12 cells. Aurintricarboxylic acid inhibits apoptosis in many cell types. Its neuroprotective effect, perhaps due to its ability to prevent down-regulation of Ca2+ impermeable GluR2 receptors or to its ability to inhibit calpain, a Ca2+-activated protease that is activated during apoptosis.

Other Notes

May contain a substantial amount of polymeric material.

Safety & Documentation

Safety Information

Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 2
RTECS 
GU4800000
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Certificate of Origin (COO)

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Meet Synthia - Retrosynthesis Sofware
Protocols & Articles
Peer-Reviewed Papers
15

References

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