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492-27-3

492-27-3 Structure

492-27-3 Structure
IdentificationMore
[Name]

KYNURENIC ACID
[CAS]

492-27-3
[Synonyms]

4-HYDROXQUINOLINE-2-CARBOXYLIC ACID
4-HYDROXYQUINALDIC ACID
4-HYDROXYQUINOLINE-2-CARBOXYLIC ACID
AKOS 235-06
KYNURENIC ACID
TIMTEC-BB SBB003671
4-Hydroxy-2-quinolincarboxylicacid
2-Quinolinecarboxylic acid, 4-hydroxy-
4-hydroxy-2-Quinolinecarboxylic acid
Quinurenic acid.
KYNURENIC ACID PURE
[EINECS(EC#)]

207-751-5
[Molecular Formula]

C10H7NO3
[MDL Number]

MFCD00006753
[Molecular Weight]

189.17
[MOL File]

492-27-3.mol
Chemical PropertiesBack Directory
[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 ]

5327
[BRN ]

147451
[InChI]

1S/C10H7NO3/c12-9-5-8(10(13)14)11-7-4-2-1-3-6(7)9/h1-5H,(H,11,12)(H,13,14)
[InChIKey]

HCZHHEIFKROPDY-UHFFFAOYSA-N
[SMILES]

OC(=O)c1cc(O)c2ccccc2n1
[CAS DataBase Reference]

492-27-3(CAS DataBase Reference)
[EPA Substance Registry System]

492-27-3(EPA Substance)
Safety DataBack Directory
[Hazard Codes ]

Xi
[Risk Statements ]

R36/37/38:Irritating to eyes, respiratory system and skin .
[Safety Statements ]

S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing .
[WGK Germany ]

3
[RTECS ]

UZ9300000
[HS Code ]

2933.49.7000
[Storage Class]

11 - Combustible Solids
Hazard InformationBack Directory
[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.
[Uses]

An antagonist of NMDA and AMPA/kainate receptors
[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.]
Spectrum DetailBack Directory
[Spectrum Detail]

KYNURENIC ACID(492-27-3)1HNMR
KYNURENIC ACID(492-27-3)IR1
KYNURENIC ACID(492-27-3)IR2
Well-known Reagent Company Product InformationBack Directory
[Sigma Aldrich]

492-27-3(sigmaaldrich)
[TCI AMERICA]

Kynurenic Acid  Hydrate,>98.0%(LC)(T)(492-27-3)
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