5,5'-(3-Carboxy-4-oxocyclohexa-2,5-dienylidenmethylen)disalicylsure

Aurintricarboxylic Acid

HCID 2259CAS 4431-00-9
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Grundinformationen

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
Summenformel
C22H14O9
Durchschnittliche Molmasse
422,3 g/mol
Monoisotopische Masse
422,06378203

Überblick

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.

Namen und Bezeichner

Bevorzugter Name
Aurintricarboxylic Acid
IUPAC
5-[(3-carboxy-4-hydroxyphenyl)-(3-carboxy-4-oxocyclohexa-2,5-dien-1-ylidene)methyl]-2-hydroxybenzoic acid
Lokaler Name
5,5'-(3-Carboxy-4-oxocyclohexa-2,5-dienylidenmethylen)disalicylsure
Englischer Name
Aurintricarboxylic acid
Summenformel
C22H14O9
Molmasse
422.34

Namen und Synonyme

aurintricarboxylic acid4431-00-9Aluminon free acidaurin tricarboxylic acidNP9O8E29QWAcid, AurintricarboxylicBenzoic acid, 5-((3-carboxy-4-hydroxyphenyl)(3-carboxy-4-oxo-2,5-cyclohexadien-1-ylidene)methyl)-2-hydroxy-CHEBI:87397Benzoic acid, 5-[(3-carboxy-4-hydroxyphenyl)(3-carboxy-4-oxo-2,5-cyclohexadien-1-ylidene)methyl]-2-hydroxy-RefChem:560355Acid, Aurin Tricarboxylicaurine tricarboxylic acid
Weitere Namen anzeigen
AURINTRICARBONIC ACIDbis(2-hydroxybenzoic acid)ATASKL331e)-6-oxo-aluminonfreeacidTIMTEC-BB SBB005410aurintricarboxylicaciLABOTEST-BB LT00080677
Dupont ATA5,5'-((3-Carboxy-4-oxocyclohexa-2,5-dien-1-ylidene)methylene)bis(2-hydroxybenzoic acid)Lopac-A-1895MFCD000116635-[(3-carboxy-4-hydroxyphenyl)-(3-carboxy-4-oxocyclohexa-2,5-dien-1-ylidene)methyl]-2-hydroxybenzoic acidAurintricarboxylicacid(ATA)chrome violet CG free acidLopac0_000054

Datenbank-Bezeichner

CAS
4431-00-9
PubChem CID
2259
DTXSID
DTXSID9063453
ChEMBL
CHEMBL275938
ChEBI
CHEBI:87397
UNII
NP9O8E29QW
EC Number
224-628-1
Nikkaji
J33.393J

Eigenschaften

Berechnete Struktureigenschaften

XLogP
4,3
Polarare Oberfläche (TPSA)
169 Ų
H-Brücken-Donoren
5
H-Brücken-Akzeptoren
9
Frei drehbare Bindungen
5
Schwere Atome
31

Experimentelle und physikochemische Eigenschaften

Chemical ClassesDyes -> Di- and Triaryl Dyes
Physical DescriptionDark red powder; [Alfa Aesar MSDS]
Collision Cross Section197.6 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

Physikochemische Eigenschaften

Schmelzpunkt
300 °C · 300 °C(lit.)
Siedepunkt
458.99 °C · 458.99°C (rough estimate)
Dichte
1.386 · 1.3860 (rough estimate)
Brechungsindex
1.623 · 1.6230 (estimate)
storage temp.
15 C · +15C to +30C
Löslichkeit
1 M · 1 M NH4OH: 10 mg/mL

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 4 Einträge

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.

Gefahrenhinweise

Hazards SummaryA skin and strong eye irritant; [Alfa Aesar MSDS]
Hazard Classes and CategoriesSkin Irrit. 2 (100%)

Sicherheitsdaten

wgk
3
tsca
TSCA listed
RTECS-Nr.
GU4790000
risk_code
36/37/38
hazard_code
Xi
safety_code
26-36

Chemie und Industrie

Verwendung und Herstellung

UsesA 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. [ChemIDplus]
General Manufacturing InformationBenzoic acid, 3,3'-[(3-carboxy-4-oxo-2,5-cyclohexadien-1-ylidene)methylene]bis[6-hydroxy-: ACTIVE
Anwendungen · 1 Eintrag

VerwendenAurintricarboxylic 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.

Vor- und nachgelagerte Produkte

Anbieter50 Anbieter

湖南韵邦生物科技股份有限公司85561037 15386497078 · [email protected]
上海康朗生物科技有限公司021-61998208 18217752821 · [email protected]
上海哲研生物科技有限公司021-18017610038 18017610038 · [email protected]
上海优宁维生物科技股份有限公司15921930842 15921930842 · [email protected]
上海如吉生物科技发展有限公司+86-21-65211385-8001 36031160 · [email protected]
Ergänzende Hinweise · 1 Eintrag

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'.

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