Grundinformationen
- CAS
59-00-7- Standard-SMILES
O=C(O)c1cc(=O)c2cccc(O)c2[nH]1- InChIKey
FBZONXHGGPHHIY-UHFFFAOYSA-N- Summenformel
- C10H7NO4
- Durchschnittliche Molmasse
- 205,17 g/mol
- Monoisotopische Masse
- 205,0375077
Überblick
Xanthurenic acid is a quinolinemonocarboxylic acid that is quinoline-2-carboxylic acid substituted by hydroxy groups at C-4 and C-8. It has a role as an iron chelator, a metabotropic glutamate receptor agonist, a vesicular glutamate transport inhibitor and an animal metabolite. It is a dihydroxyquinoline and a quinolinemonocarboxylic acid. It is a conjugate acid of a xanthurenate.
Namen und Bezeichner
- Bevorzugter Name
- Xanthurenic Acid
- IUPAC
- 8-hydroxy-4-oxo-1H-quinoline-2-carboxylic acid
- Lokaler Name
- 4,8-Dihydroxychinolin-2-carbonsure
- Englischer Name
- Xanthurenic acid
- Summenformel
- C10H7NO4
- Molmasse
- 205.17
Namen und Synonyme
xanthurenic acid59-00-74,8-Dihydroxyquinoline-2-carboxylic acidXanthuric acid8-Hydroxykynurenic acid4,8-Dihydroxyquinaldic acid8-hydroxy-4-oxo-1H-quinoline-2-carboxylic acid58LAB1BG8JNSC-401570DTXSID90207728CHEBI:10072RefChem:902266
Weitere Namen anzeigen
NSC 401570JACS-59-00-7XENTHURENIC ACIDTIMTEC-BB SBB003498XANTHURENIC ACID(RG)Xanthurenic acid 96%
DTXCID40130219200-410-1Xanthurenate4,8-Dihydroxyquinaldinic acid2-Quinolinecarboxylic acid, 4,8-dihydroxy-4,8-Dihydroxy-2-quinolinecarboxylic acid8-hydroxy-4-oxo-1,4-dihydroquinoline-2-carboxylic acidMFCD00006754
Datenbank-Bezeichner
- CAS
59-00-7- PubChem CID
- 5699
- DTXSID
DTXSID90207728- ChEMBL
CHEMBL312535
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 0,9
- Polarare Oberfläche (TPSA)
- 86,6 Ų
- H-Brücken-Donoren
- 3
- H-Brücken-Akzeptoren
- 5
- Frei drehbare Bindungen
- 1
- Schwere Atome
- 15
- Formalladung
- 0
- Komplexität
- 336
Experimentelle und physikochemische Eigenschaften
Melting Point289 °C
Physical DescriptionSolid
Collision Cross Section
137.7 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
132.51 Ų [M-H]- [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]
140.4 Ų [M+H]+ [CCS Type: DT; Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]
134.6 Ų [M-H]-
Physikochemische Eigenschaften
- Schmelzpunkt
- 297 · 297-298 °C (dec.)(lit.)
- Siedepunkt
- 343.83 °C · 343.83°C (rough estimate)
- Dichte
- 1.3849 · 1.3849 (rough estimate)
- Brechungsindex
- 1.56 · 1.5600 (estimate)
- storage temp.
- 2 · Sealed in dry,2-8°C
- Löslichkeit
- DMSO (Slightly, Heated), Water (Slightly, Heated)
- Aggregatzustand
Sicherheit und Regulatorisches
GHS-Klassifizierung
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 40 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Gefahrenhinweise
Regulatory Information2-Quinolinecarboxylic acid, 4,8-dihydroxy-: Does not have an individual approval but may be used under an appropriate group standard
Hazard Classes and CategoriesSkin Irrit. 2 (100%)
Sicherheitsdaten
- wgk
- 3
- hs_code
- 29334900
- RTECS-Nr.
- UZ9275000
- risk_code
- 36/37/38
- hazard_code
- Xi
- safety_code
- 26-36-37/39
- Speicherklasse
- 11 - Combustible Solids
Chemie und Industrie
Pharmakologische Informationen
Metabolism/MetabolitesXanthurenic acid has known human metabolites that include Xanthurenic acid 8-O-sulfate.
MeSH Pharmacological ClassificationSubstances that lower the levels of certain LIPIDS in the BLOOD. They are used to treat HYPERLIPIDEMIAS.
Tissue LocationsEpidermis
Cellular LocationsMembrane
Metabolite PathwaysTryptophan metabolism
Anwendungen
VerwendenXanthurenic acid can be used as a substrate for the synthesis of: Silica-gel functionalized xanthurenic acid (4, 8-dihydroxyquinoline-2-carboxylic acid) as an adsorbent for metal ions.N, N′-bis-((8-hydroxy-7-quinolinyl)methyl)-1,10-diaza-18-crown-6 ethers as fluorescent sensors of magnesium in living cells via one-pot Mannich reaction.Poly-xanthurenic acid (poly-Xa) for biosensing applications.
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