Basic information
- CAS
4431-00-9- Standard SMILES
O=C(O)C1=CC(=C(c2ccc(O)c(C(=O)O)c2)c2ccc(O)c(C(=O)O)c2)C=CC1=O- InChIKey
GIXWDMTZECRIJT-UHFFFAOYSA-N- Molecular formula
- C22H14O9
- Average molar mass
- 422.3 g/mol
- Monoisotopic mass
- 422.06378203
Overview
Aurintricarboxylic acid is 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'. It has a role as a fluorochrome, an insulin-like growth factor receptor 1 antagonist and a histological dye. It is a monohydroxybenzoic acid, a tricarboxylic acid and a member of quinomethanes. It is a conjugate acid of an aurintricarboxylate.
Names & identifiers
- Preferred name
- Aurintricarboxylic Acid
- IUPAC
- 5-[(3-carboxy-4-hydroxyphenyl)-(3-carboxy-4-oxocyclohexa-2,5-dien-1-ylidene)methyl]-2-hydroxybenzoic acid
- English name
- Aurintricarboxylic acid
- Molecular formula
- C22H14O9
- Molecular weight
- 422.34
Names & synonyms
Show more names
Database identifiers
- CAS
4431-00-9- PubChem CID
- 2259
- DTXSID
DTXSID9063453- ChEMBL
CHEMBL275938- ChEBI
CHEBI:87397- UNII
- NP9O8E29QW
- EC Number
- 224-628-1
- Nikkaji
- J33.393J
Properties
Computed structural properties
- XLogP
- 4.3
- Topological polar surface area
- 169 Ų
- Hydrogen bond donors
- 5
- Hydrogen bond acceptors
- 9
- Rotatable bonds
- 5
- Heavy atoms
- 31
- Formal charge
- 0
- Complexity
- 841
Experimental & physicochemical properties
Physicochemical properties
- Melting point
- 300 °C · 300 °C(lit.)
- Boiling point
- 458.99 °C · 458.99°C (rough estimate)
- Density
- 1.386 · 1.3860 (rough estimate)
- refractive index
- 1.623 · 1.6230 (estimate)
- storage temp.
- 15 C · +15C to +30C
- solubility
- 1 M · 1 M NH4OH: 10 mg/mL
- form
- powder
- pka
- 2.2 · 2.20±0.20(Predicted)
- color
- dark red to brown
- Water Solubility
- Insoluble in water.
- BRN
- 2228904 · 2228904
- Major Application
- diagnostic assay manufacturinghematologyhistology
- 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 · 4431-00-9(CAS DataBase Reference)
- FDA UNII
- 9 O8E29QW · NP9O8E29QW
- EPA Substance Registry System
- 5 · Benzoic acid, 5-[(3-carboxy-4-hydroxyphenyl)(3-carboxy-4-oxo-2,5-cyclohexadien-1-ylidene)methyl]-2-hydroxy- (4431-00-9)
- UNSPSC Code
- 12352106 · 12352106
- NACRES
- 77 · NA.77
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 315 · H315-H319-H335
- Precautionary statements
- 261 · P261-P280a-P304+P340-P305+P351+P338-P405-P501a
- PPE
- 95 · dust mask type N95 (US), Eyeshields, Gloves
- Hazard Codes
- Xi
- Risk Statements
- 36 · 36/37/38
- Safety Statements
- 26 · 26-36
- WGK Germany
- 3 · 3
- RTECS
- 4790000 · GU4790000
- TSCA
- TSCA listed
- Storage Class
- 11 · 11 - Combustible Solids
Safety & regulation
GHS classification
GHS Classification
Warning
H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 43 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Safety data
- PPE
- dust mask type N95 (US), Eyeshields, Gloves
- wgk
- 3
- tsca
- TSCA listed
- rtecs
- GU4790000
- risk_code
- 36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi
- safety_code
- 26-36
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H315-H319-H335
- Precautionary statements
- P261-P280a-P304+P340-P305+P351+P338-P405-P501a
Chemistry & industry
Uses & manufacturing
Applications
Usesendonuclease inhibitor; apoptosis inhibitor, topoisomerase II inhibitor
UsesAurintricarboxylic 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.
Upstream & downstream products
Upstream raw materials
Suppliers70 total
Additional notes
DefinitionChEBI: 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'.
Related reactions
No reaction records under the current filter.
Compound notes
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