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A1895

Sigma-Aldrich

Aurintricarboxylic acid

practical grade, ≥85% (titration), powder

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Synonym(s):
ATA
Empirical Formula (Hill Notation):
C22H14O9
CAS Number:
4431-00-9
Molecular Weight:
422.34
EC Number:
224-628-1
MDL number:
MFCD00011663
PubChem Substance ID:
24278210
NACRES:
NA.47

grade

practical grade

Quality Level

300

Assay

≥85% (titration)

form

powder

color

dark red to brown

mp

300 °C (lit.)

solubility

1 M NH4OH: 10 mg/mL

application(s)

diagnostic assay manufacturing
hematology
histology

storage temp.

room temp

SMILES string

OC(=O)c1cc(ccc1O)C(\c2ccc(O)c(c2)C(O)=O)=C3\C=CC(=O)C(=C3)C(O)=O

InChI

1S/C22H14O9/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)

InChI key

GIXWDMTZECRIJT-UHFFFAOYSA-N

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This Item
A36883A0885189400
Aurintricarboxylic acid practical grade, ≥85% (titration), powder

Sigma-Aldrich

A1895

Aurintricarboxylic acid

Aurintricarboxylic acid ammonium salt ACS reagent

Sigma-Aldrich

A36883

Aurintricarboxylic acid ammonium salt

Aurintricarboxylic acid ammonium salt powder

Sigma-Aldrich

A0885

Aurintricarboxylic acid ammonium salt

Aurintricarboxylic Acid A cell-permeable polyanionic, polyaromatic compound used as a powerful inhibitor of cellular processes that are dependent on the formation of protein-nucleic acid complexes.

Sigma-Aldrich

189400

Aurintricarboxylic Acid

assay

≥85% (titration)

assay

-

assay

-

assay

≥85% (titration)

form

powder

form

powder or crystals

form

powder

form

solid

color

dark red to brown

color

-

color

-

color

red

mp

300 °C (lit.)

mp

220-225 °C (dec.) (lit.)

mp

220-225 °C (dec.) (lit.)

mp

-

solubility

1 M NH4OH: 10 mg/mL

solubility

water: soluble 100 mg/mL

solubility

water: soluble 100 mg/mL, dark red

solubility

0.1 M NaOH: 35 mg/mL

Application

  • Aurintricarboxylic acid has been used to show its anticryptosporidial activity against Cryptosporidium parvum.
  • It has been used as a test substance to identify inhibitors against coronavirus N7-MTases (guanine-N7-methyltransferase).
  • It has been used as a ribonuclease inhibitor.

Biochem/physiol Actions

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 Cγ in PC12 cells. Inhibits apoptosis. It prevents down-regulation of Ca2+ -impermeable GluR2 receptors and inhibits calpain, a Ca2+ -activated protease that is activated during apoptosis.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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In vitro and in vivo activity of aurintricarboxylic acid preparations against Cryptosporidium parvum.
Klein P, et al.
The Journal of Antimicrobial Chemotherapy, 62, 1101-1104 (2008)
Yeast-based assays for the high-throughput screening of inhibitors of coronavirus RNA cap guanine-N7-methyltransferase.
Sun Y, et al.
Antiviral Research, 104, 156-164 (2014)
Red Light-Independent Instability of Oat Phytochrome mRNA in Vivo.
Seeley KA, et al.
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