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KYNURENIC ACID

CAS No.
492-27-3
Chemical Name:
KYNURENIC ACID
Synonyms
NSC 58973;AKOS 235-06;KYNURENIC ACID;Quinurenic acid.;TIMTEC-BB SBB003671;KYNURENIC ACID PURE;2H5]-Kynurenic acid;4-HYDROXYQUINALDIC ACID;KynurenicAcidHydrate>Difelikefalin Impurity 9
CBNumber:
CB3711231
Molecular Formula:
C10H7NO3
Molecular Weight:
189.17
MDL Number:
MFCD00006753
MOL File:
492-27-3.mol
MSDS File:
SDS
Last updated:2023-06-30 15:45:59

KYNURENIC ACID 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.
pka 1.08±0.30(Predicted)
color White to Gray to Brown
Water Solubility 8.92g/L(100 ºC)
Merck 14,5327
BRN 147451
CAS DataBase Reference 492-27-3(CAS DataBase Reference)
EWG's Food Scores 1
FDA UNII H030S2S85J
EPA Substance Registry System 2-Quinolinecarboxylic acid, 4-hydroxy- (492-27-3)

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
GHS07
Signal word  Warning
Hazard statements  H315-H319-H335
Precautionary statements  P264-P280-P302+P352-P321-P332+P313-P362-P264-P280-P305+P351+P338-P337+P313P
Hazard Codes  Xi
Risk Statements  36/37/38
Safety Statements  26-36
WGK Germany  3
RTECS  UZ9300000
HS Code  2933.49.7000
NFPA 704
1
2 0

KYNURENIC ACID Chemical Properties,Uses,Production

Uses

An antagonist of NMDA and AMPA/kainate receptors

Uses

Kynurenic 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.

Uses

A product of L-Tryptophan metabolism, possessing neruoactive activity having antiexcitotoxic and anticonvulsant properties.

Definition

ChEBI: 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 Activity

Broad spectrum EAA antagonist.

Biochem/physiol Actions

Kynurenic 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.

storage

Room temperature

Purification Methods

Crystallise 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

Raw materials

Preparation Products

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 Kynurenic acid,4-Hydroxyquinoline-2-carboxylic acid AKOS 235-06 4-HYDROXQUINOLINE-2-CARBOXYLIC ACID 4-HYDROXYQUINALDIC ACID 4-HYDROXYQUINOLINE-2-CARBOXYLIC ACID TIMTEC-BB SBB003671 4-Hydroxyquinaldic Acid Hydrate 4-Hydroxy-2-quinolincarboxylicacid 4-hydroxy-2-Quinolinecarboxylic acid Quinurenic acid. 2-Quinolinecarboxylic acid, 4-hydroxy- KYNURENIC ACID PURE 4-oxido-2-quinolinecarboxylate KynurenicAcidHydrate> 4-Hydroxyquinoline-2-carboxylicacid98% 2H5]-Kynurenic acid Difelikefalin Impurity 9 492-27-3 492-22-3 HOC9H5NCOOH C9H5NOHCOOH Heterocyclic Building Blocks Ionotropic Glutamate Receptor Modulators Ion Channels Ligand-Gated Ion Channels Hydroxyquinolines Quinolines Cell Signaling and Neuroscience Cell Biology Building Blocks BioChemical 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