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

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 Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

RTECS 

GU4790000

TSCA 

Yes

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

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'.

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(4431-00-9)Related Product Information

• Sorbic acid
• Aluminon
• 3-VINYLBENZALDEHYDE
• 5-PHENYLPENTA-2,4-DIENOIC ACID
• 5-Methylsalicylaldehyde
• TRANS-2-PENTENOIC ACID
• TRANS-2-PENTEN-1-OL
• 5-Methylsalicylic acid
• 5,5'-Methylenedisalicylic acid
• 2,4-DIMETHYL-1,3-PENTADIENE
• 1-METHYL-1,4-CYCLOHEXADIENE
• (E,E)-2,4-Hexadienal
• TRANS,TRANS-2,4-HEXADIEN-1-OL
• trans-2-Methyl-2-pentenoic acid
• m,alpha-dimethylstyrene
• AURINTRICARBOXYLIC ACID
• ROSOLIC ACID
• Allylacetic acid