ChemicalBook--->CAS DataBase List--->4431-00-9

4431-00-9

4431-00-9 Structure

4431-00-9 Structure
IdentificationMore
[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 PropertiesBack 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
[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 DataBack 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
Raw materials And Preparation ProductsBack Directory
[Raw materials]

4-Nitrobenzoyl chloride-->Methylenedisalicylic acid-->5,5'-Methylenedisalicylic acid-->NITROUS ACID-->Sulfuric acid-->Methanol-->Formaldehyde-->Salicylic acid
Hazard InformationBack 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.
Spectrum DetailBack Directory
[Spectrum Detail]

AURINTRICARBOXYLIC ACID(4431-00-9)IR1
AURINTRICARBOXYLIC ACID(4431-00-9)IR2
Well-known Reagent Company Product InformationBack Directory
[Alfa Aesar]

Aurintricarboxylic acid(4431-00-9)
[Sigma Aldrich]

4431-00-9(sigmaaldrich)
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