KYNURENIC ACID Property

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

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

RTECS 

UZ9300000

HS Code 

2933.49.7000

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P321Specific treatment (see … on this label).

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P362Take off contaminated clothing and wash before reuse.

KYNURENIC ACID Chemical Properties,Usage,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.]