| Identification | More | [Name]
AURINTRICARBOXYLIC ACID | [CAS]
4431-00-9 | [Synonyms]
ATA
AURINTRICARBOXYLIC ACID
LABOTEST-BB LT00080677
TIMTEC-BB SBB005410
1,4-cyclohexadiene-1-carboxylicacid,3-(bis(3-carboxy-4-hydroxyphenyl)methylen
5-[(3-carboxy-4-hydroxyphenyl)(3-carboxy-4-oxo-2,5-cyclohexadien-benzoicaci
aluminonfreeacid
e)-6-oxo-
5,5-(3-carboxy-4-oxocyclohexa-2,5-dienylidenemethylene)di(salicylic acid)
aurinetricarboxylic acid
AURINTRICARBOXYLIC ACID FREE ACIDPRACTIC AL GRADE
Aurintricarboxylic Acid (Ata)
AURINTRICARBONIC ACID
Aurintricarboxylic acid, tech., 85%
1-Oxo-4-[bis(3-carboxy-4-hydroxyphenyl)methylene]-2,5-cyclohexadiene-2-carboxylic acid
5,5'-[(3-Carboxy-4-oxo-2,5-cyclohexadien-1-ylidene)methylene]bis(2-hydroxybenzoic acid) | [EINECS(EC#)]
224-628-1 | [Molecular Formula]
C22H14O9 | [MDL Number]
MFCD00011663 | [Molecular Weight]
422.34 | [MOL File]
4431-00-9.mol |
| Chemical Properties | Back Directory | [Appearance]
deep red coarse crystalline powder | [Melting point ]
300 °C(lit.) | [Boiling point ]
458.99°C (rough estimate) | [density ]
1.3860 (rough estimate) | [refractive index ]
1.6230 (estimate) | [storage temp. ]
+15C to +30C | [solubility ]
1 M NH4OH: 10 mg/mL
| [form ]
powder
| [pka]
2.20±0.20(Predicted) | [color ]
dark red to brown
| [Water Solubility ]
Insoluble in water. | [BRN ]
2228904 | [Major Application]
diagnostic assay manufacturing
hematology
histology | [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) | [InChIKey]
GIXWDMTZECRIJT-UHFFFAOYSA-N | [SMILES]
OC(=O)c1cc(ccc1O)C(\c2ccc(O)c(c2)C(O)=O)=C3\C=CC(=O)C(=C3)C(O)=O | [CAS DataBase Reference]
4431-00-9(CAS DataBase Reference) | [EPA Substance Registry System]
Benzoic acid, 5-[(3-carboxy-4-hydroxyphenyl)(3-carboxy-4-oxo-2,5-cyclohexadien-1-ylidene)methyl]-2-hydroxy- (4431-00-9) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing . | [WGK Germany ]
3
| [RTECS ]
GU4790000
| [TSCA ]
Yes | [Storage Class]
11 - Combustible Solids |
| Hazard Information | Back Directory | [Chemical Properties]
deep red coarse crystalline powder | [Uses]
Aurintricarboxylic acid is employed as a powerful inhibitor of cellular processes, including apoptosis, that are dependent on the formation of protein-nucleic acid complexes. It binds to a FGF and reduces its angiogenic activity. Aurintricarboxylic Acid has been shown to inhibit apoptotic cell death in various cell types induced by a variety of factors. It Inhibits protein-nucleic acid interactions. It stimulates the tyrosine phosphorylation of MAP kinases. | [Uses]
endonuclease inhibitor; apoptosis inhibitor, topoisomerase II inhibitor | [Definition]
ChEBI: A member of the class of quinomethanes that is 3-methylidene-6-oxocyclohexa-1,4-diene-1-carboxylic acid in which the methylidene hydrogens are replaced by 4-carboxy-3-hydroxyphenyl groups. The trisodium salt is the biological stain 'chrome violet CG' while
the triammonium salt is 'aluminon'. | [Biological Activity]
Readily polymerizes in aqueous solutionforming a stable free radical th at 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 cellsand MAP kinasesShc proteinsphosphatidylinositide 3-kinase and phospholipase Cγ in PC12 cells. Inhibits apoptosis. It prevents down-regulation of Ca2+ -impermeable GluR2 receptors and inhibits calpaina Ca2+ -activated protease th at is activated during apoptosis. | [Purification Methods]
The acid is dissolved in aqueous NaOH, NaHSO3 solution is added until the colour is discharged and then the tricarboxylic acid is precipitated with HCl. [Heisig & Lauer Org Synth Coll Vol I 54 1941, Beilstein 10 IV 4161]. Do not extract the acid with hot water because it softens, forming a viscous mass. Make a solution in aqueous NH3. Aluminon is the NH4 salt. |
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