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| | AURINTRICARBOXYLIC ACID Basic information |
| Product Name: | AURINTRICARBOXYLIC ACID | | Synonyms: | Aurintricarboxylic Acid - CAS 4431-00-9 - Calbiochem;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-dien-1-ylidene);bis(2-hydroxybenzoic acid);TIMTEC-BB SBB005410 | | CAS: | 4431-00-9 | | MF: | C22H14O9 | | MW: | 422.34 | | EINECS: | 224-628-1 | | Product Categories: | Colours, Dyes, Indicators & Pigments | | Mol File: | 4431-00-9.mol |  |
| | AURINTRICARBOXYLIC ACID Chemical Properties |
| 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 | | pka | 2.20±0.20(Predicted) | | form | powder | | 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) |
| Hazard Codes | Xi | | Risk Statements | 36/37/38 | | Safety Statements | 26-36 | | WGK Germany | 3 | | RTECS | GU4790000 | | TSCA | TSCA listed | | Storage Class | 11 - Combustible Solids |
| | AURINTRICARBOXYLIC ACID Usage And Synthesis |
| Chemical Properties | deep red coarse crystalline powder | | Uses | endonuclease inhibitor; apoptosis inhibitor, topoisomerase II inhibitor | | 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. | | 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 solution, forming 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 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 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. |
| | AURINTRICARBOXYLIC ACID Preparation Products And Raw materials |
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