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.

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)

EPA Substance Registry System

2-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

• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

KYNURENIC ACID Usage And Synthesis

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(492-27-3)Related Product Information

• METHYL 6-BROMO-4-HYDROXYQUINOLINE-2-CARBOXYLATE
• KYNURENIC ACID
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• KETAMINE HYDROCHLORIDE - REFERENCE SPECTRUM
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• xanthurenic acid 8-methyl ether
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