5-[(3-carboxy-4-hydroxyphenyl)(3-carboxy-4-oxocyclohexa-2,5-dien-1-ylidene)methyl]-2-hydroxybenzoic acid

• ChemBase ID: 104121
• Molecular Formular: C22H14O9
• Molecular Mass: 422.34116
• Monoisotopic Mass: 422.06378203
• SMILES: OC(=O)c1c(O)ccc(c1)/C(=C\1/C=CC(=O)C(=C1)C(=O)O)/c1cc(C(=O)O)c(O)cc1
• Canonical SMILES: OC(=O)C1=C/C(=C(\c2ccc(c(c2)C(=O)O)O)/c2ccc(c(c2)C(=O)O)O)/C=CC1=O
• InChI: 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

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-[(3-carboxy-4-hydroxyphenyl)(3-carboxy-4-oxocyclohexa-2,5-dien-1-ylidene)methyl]-2-hydroxybenzoic acid
• IUPAC Traditional name: aurintricarboxylic acid
• Synonyms: Aluminon free acid; ATA; Aurintricarboxylic acid; AURINTRICARBOXYLIC ACID; 金精三羧酸

Database IDs

• CAS Number: 4431-00-9
• EC Number: 224-628-1
• MDL Number: MFCD00011663
• Beilstein Number: 2228904
• PubChem SID: 24278210; 162091412
• PubChem CID: 2259
• CHEMBL: 275938
• Chemspider ID: 2172
• Wikipedia Title: Aurintricarboxylic_acid

CALCULATED PROPERTIES

• Acid pKa: 2.30886
• H Acceptors: 9
• H Donor: 5
• LogD (pH = 5.5): -3.3771243
• LogD (pH = 7.4): -6.296875
• Log P: 4.0548306
• Molar Refractivity: 118.6298 cm^3
• Polarizability: 39.86178 Å^3
• Polar Surface Area: 169.43 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: 1 M NH4OH: soluble10 mg/mL
• Apperance: Dark red to brown powder; dark red to brown powder
• Melting Point: >300°C; 300 °C(lit.); 300°C
• Absorption Wavelength: λmax 552 nm

Safety Information

• Storage Condition: Room Temperature (15-30°C)
• RTECS: GU4790000
• European Hazard Symbols: Irritant (Xi); Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 36/37/38; R:22
• Safety Statements: 26; 26-37; S:36/37/39
• TSCA Listed: 是
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: ≥85% (titration)
• Grade: practical grade
• Compostion: Dye content, 85%
• Empirical Formula (Hill Notation): C22H14O9

DETAILS

MP Biomedicals - 02154800

Free Acid

MP Biomedicals - 05207718

MP Biomedicals Rare Chemical collection

Sigma Aldrich - A1895

Biochem/physiol Actions
易于在水溶液中聚合，形成可抑制蛋白质-核酸相互作用的稳定自由基。它是核糖核酸酶和拓扑异构酶 II 的强效抑制剂，作用机理是阻止核酸与酶的结合。其可促进酪氨酸磷酸化过程，包括 NB2 淋巴瘤细胞中的 Jak2/STAT5 通路，神经母细胞瘤细胞中的 ErbB4，以及 PC12 细胞中的 MAP 激酶、Shc 蛋白、磷脂酰肌醇 3-激酶和磷脂酶 Cγ。抑制细胞凋亡。它可阻止对 Ca2+ 不通透的 GluR2 受体的下调并抑制钙蛋白酶，这是一种在细胞凋亡过程中被活化的 Ca2+ -激活蛋白酶。

Sigma Aldrich - 123269

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.
Other Notes
May contain a substantial amount of polymeric material
Application
Used extensively as a powerful inhibitor of cellular processes which are dependent on the formation of protein-nucleic acid complexes.1,2