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Aurintricarboxylic acid

Aurintricarboxylic acid structure

CAS No:
4431-00-9
Formula:
C22H14O9
Chemical Name:
Aurintricarboxylic acid
Synonyms:
Benzoic acid,3,3′-[(3-carboxy-4-oxo-2,5-cyclohexadien-1-ylidene)methylene]bis[6-hydroxy-;1,4-Cyclohexadiene-1-carboxylic acid,3-[bis(3-carboxy-4-hydroxyphenyl)methylene]-6-oxo-;Aurintricarboxylic acid;Benzoic acid,5-[(3-carboxy-4-hydroxyphenyl)(3-carboxy-4-oxo-2,5-cyclohexadien-1-ylidene)methyl]-2-hydroxy-;3,3′-[(3-Carboxy-4-oxo-2,5-cyclohexadien-1-ylidene)methylene]bis[6-hydroxybenzoic acid];Aluminon free acid;Aurine tricarboxylic acid;CAC 1098;CP 005240;857155-55-6
Categories:
Pharmaceutical Intermediates > Bulk Drug Intermediates

Description

Aurintricarboxylic acid is a nanomolar-potency, allosteric antagonist with selectivity towards αβ-methylene-ATP-sensitive P2X1Rs and P2X3Rs, with IC50s of 8.6 nM and 72.9 nM for rP2X1R and rP2X3R, respectively[1]. Aurintricarboxylic acid is a potent anti-influenza agent by directly inhibiting the neuraminidase[2]. Aurintricarboxylic acid is an inhibitor of topoisomerase II and apoptosis[3]. Aurintricarboxylic acid is a selective inhibitor of the TWEAK-Fn14 signaling pathway[4].

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 histological dye, an insulin-like growth factor receptor 1 antagonist and a fluorochrome. It is a monohydroxybenzoic acid, a member of quinomethanes and a tricarboxylic acid. It is a conjugate acid of an aurintricarboxylate.|A dye which inhibits protein biosynthesis at the initial stages. The ammonium salt (aluminon) is a reagent for the colorimetric estimation of aluminum in water, foods, and tissues.

Aurintricarboxylic acid Basic Attributes

Molecular Weight：

422.34

Exact Mass：

422.34

BRN：

2228904

EC Number：

224-628-1

UNII：

NP9O8E29QW

DSSTox ID：

DTXSID9063453

Characteristics

PSA：

169

XLogP3：

4.09

Appearance：

dark red to brown powder

Density：

1.6±0.1 g/cm3

Melting Point：

300 °C(lit.)

Boiling Point：

759.6±60.0 °C at 760 mmHg

Flash Point：

427.1±29.4 °C

Refractive Index：

1.751

Water Solubility：

Insoluble in water.1 M NH4OH: 10 mg/mL

Storage Conditions：

+15C to +30C

Collision Cross Section：

197.6 Å² [M+H]+ [CCS Type: TW, Method: calibrated with polyalanine and drug standards]

Safety Information

Transport codes：

NONH for all modes of transport

wgk germany：

hazard class code：

36/37/38

safety instructions：

26-36

RTECS Number：

GU4790000

Marks：

Precautionary statement(s)：

P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501

Hazard Statements：

H315

GHS Classification：

|Warning|H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 44 companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Drug Information

MeSH Entry Terms：

Acid, Aurin Tricarboxylic

Aurintricarboxylic acid Use and Manufacturing

Methods of Manufacturing

Salicylic acid reacts with formaldehyde to obtain methylene disalicylic acid, which is then mixed and reacted with salicylic acid and nitrosylthioester to obtain golden tricarboxylic acid.

Uses

endonuclease inhibitor; apoptosis inhibitor, topoisomerase II inhibitor

Manufacturing Info：

Benzoic acid, 3,3'-[(3-carboxy-4-oxo-2,5-cyclohexadien-1-ylidene)methylene]bis[6-hydroxy-: ACTIVE

Computed Properties

Molecular Weight:422.3
XLogP3:4.3
Hydrogen Bond Donor Count:5
Hydrogen Bond Acceptor Count:9
Rotatable Bond Count:5
Exact Mass:422.06378202
Monoisotopic Mass:422.06378202
Topological Polar Surface Area:169
Heavy Atom Count:31
Complexity:841
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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AURINTRICARBOXYLIC ACID

CAS No.: 4431-00-9

Grade: Industrial Grade

Content: 99%

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AURINTRICARBOXYLIC ACID

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CAS No.: 4431-00-9

Grade: Pharmaceutical Grade

Content: 99%

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