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KYNURENIC ACID

KYNURENIC ACID Basic information
Product Name:KYNURENIC ACID
Synonyms:KYNURENIC ACID;2-Carboxy-4-hydroxyquinoline;4-Hydroxyquinaldinic Acid;NSC 58973;4-Hydroxyquinaldic Acid 4-Hydroxyquinoline-2-carboxylic Acid;4-HYDROXYQUINOLINE-2-CARBOXYLIC ACID FOR;4-keto-1H-quinoline-2-carboxylic acid;4-oxo-1H-quinoline-2-carboxylic acid
CAS:492-27-3
MF:C10H7NO3
MW:189.17
EINECS:207-751-5
Product Categories:Amino Acids & Derivatives, Aromatics, Heterocycles, Pharmaceuticals, Intermediates & Fine Chemicals;Glutamate;Amino Acids & Derivatives;Aromatics;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals;Quinolines, Quinazolines and derivatives;Quinoline&Isoquinoline;Hydroxyquinolines;Quinolines;Glutamate receptor
Mol File:492-27-3.mol
KYNURENIC ACID Structure
KYNURENIC ACID Chemical Properties
Melting point 275 °C (dec.)(lit.)
Boiling point 324.41°C (rough estimate)
density 1.3175 (rough estimate)
refractive index 1.5400 (estimate)
storage temp. Sealed in dry,Room Temperature
solubility DMSO : 9 mg/mL (47.58 mM; Need ultrasonic and warming)
form Off-white to tan powder.
pka1.08±0.30(Predicted)
color White to Gray to Brown
Water Solubility 8.92g/L(100 ºC)
Merck 14,5327
BRN 147451
CAS DataBase Reference492-27-3(CAS DataBase Reference)
EPA Substance Registry System2-Quinolinecarboxylic acid, 4-hydroxy- (492-27-3)
Safety Information
Hazard Codes Xi
Risk Statements 36/37/38
Safety Statements 26-36
WGK Germany 3
RTECS UZ9300000
HS Code 2933.49.7000
MSDS Information
ProviderLanguage
SigmaAldrich English
ALFA English
KYNURENIC ACID Usage And Synthesis
UsesAn antagonist of NMDA and AMPA/kainate receptors
UsesKynurenic acid has been used as a constituent in dissection saline solution for embryonic cerebral cortical cells and human primary astrocytes. It has also been used as a medium supplement for murine intestinal epithelial cell line, MODE-K and induced pluripotent stem cell (iPSC)-derived neurons cells.
UsesA product of L-Tryptophan metabolism, possessing neruoactive activity having antiexcitotoxic and anticonvulsant properties.
DefinitionChEBI: Kynurenic acid is a quinolinemonocarboxylic acid that is quinoline-2-carboxylic acid substituted by a hydroxy group at C-4. It has a role as a G-protein-coupled receptor agonist, a NMDA receptor antagonist, a nicotinic antagonist, a neuroprotective agent, a human metabolite and a Saccharomyces cerevisiae metabolite. It is a monohydroxyquinoline and a quinolinemonocarboxylic acid. It is a conjugate acid of a kynurenate.
Biological ActivityBroad spectrum EAA antagonist.
Biochem/physiol ActionsKynurenic acid (KynA) is a non-selective antagonist of N-methyl-d-aspartate (NMDA), α-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid (AMPA) and kainate receptors. It blocks kainic acid neurotoxicity. Kynurenic acid also blocks nicotinic acetylcholine receptors. It is a by-product of tryptophan catabolic pathway. Kynurenic acid is a neuromodulator and controls the levels of glutamate, dopamine, acetylcholine and α-aminobutyric acid (GABA). KynA controls neuroendocrine functions and altered levels of KynA is a potential marker in depression, schizophrenia Alzheimer′s and Huntington′s diseases. Normal levels of KynA in the brain is crucial for the cognitive function.
storageRoom temperature
Purification MethodsCrystallise the acid from absolute EtOH. The methyl ester crystallises from MeOH with m 224-226o. [Greenstein & Winitz The Chemistry of the Amino Acids J. Wiley, Vol 3 p2723 1961, Beilstein 22 II 174, 22 III/IV 2245, 22/6 V 280.]
KYNURENIC ACID Preparation Products And Raw materials
Tag:KYNURENIC ACID(492-27-3) Related Product Information
METHYL 6-BROMO-4-HYDROXYQUINOLINE-2-CARBOXYLATE KYNURENIC ACID KETAMINE RELATED COMPOUND A (50 MG) (1 -[(2-CHLOROPHENYL)(METHYLIMINO)METHYL]CYLCOPENTA-NOL) Ketamine hydrochloride XANTHURENIC ACID 4-METHOXY-2-QUINOLINECARBOXYLIC ACID METHYL 6,8-DIFLUORO-4-HYDROXYQUINOLINE-2-CARBOXYLATE ETHYL 4-HYDROXY-2-QUINOLINECARBOXYLATE Isoconazole nitrate KETAMINE IMPURITY A (S)-(+)-Ketamine hydrochloride KETAMINE HYDROCHLORIDE - REFERENCE SPECTRUM KETAMINE/ZYLAZINE SOLUTION--SCHEDULE*III ITEM 4-Hydroxyquinoline 4-HYDROXYQUINOLINE KYNURENIC-3,5,6,7,8-D5 ACID xanthurenic acid 8-methyl ether 4-Hydroxy-7-methoxy-quinoline-2-carboxylic acid methyl ester