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A36883

Sigma-Aldrich

Aurintricarboxylic acid ammonium salt

ACS reagent, powder or crystals

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Synonym(s):
ATA, Aluminon, Ammonium aurintricarboxylate
Linear Formula:
C22H14O9 · 3NH3
CAS Number:
569-58-4
Molecular Weight:
473.43
Colour Index Number:
43810
Beilstein:
3900820
EC Number:
209-319-1
MDL number:
MFCD00040925
UNSPSC Code:
12171500
PubChem Substance ID:
24890803
NACRES:
NA.47

biological source

synthetic

Quality Level

300

grade

ACS reagent

form

powder or crystals

impurities

≤0.1% insolubles

ign. residue

≤0.2%

color

dark red

mp

220-225 °C (dec.) (lit.)

solubility

water: soluble 100 mg/mL

λmax

450 nm
522 nm (2nd)

application(s)

diagnostic assay manufacturing
hematology
histology

storage temp.

room temp

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

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Related Categories

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.

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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There is a continuing threat that the highly pathogenic avian influenza virus will cause future influenza pandemics. In this study, we screened a library of compounds that are biologically active and structurally diverse for inhibitory activity against influenza neuraminidase (NA).
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The Journal of antimicrobial chemotherapy, 65(4), 676-683 (2010-01-22)
Enterovirus 71 (EV71) causes serious diseases in humans. The aim of this study was to examine the effects of aurintricarboxylic acid (ATA) on EV71 replication and to explore the underlying mechanism. To measure the activity of ATA in inhibiting the
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