Name | 4-Hydroxyquinoline-2-carboxylic acid, hydrate |
Synonyms | NSC 58973 KYNURENIC ACID Kynurenic acid 4-Hydroxyquinaldic acid 4-Hydroxyquinaldinic Acid 2-Carboxy-4-hydroxyquinoline 4-oxo-1H-quinoline-2-carboxylic acid 4-keto-1H-quinoline-2-carboxylic acid 4-HYDROXYQUINOLINE-2-CARBOXYLIC ACID FOR 4-oxo-1,4-dihydroquinoline-2-carboxylic acid 4-Hydroxyquinoline-2-carboxylic acid hydrate 4-Hydroxyquinoline-2-carboxylic acid, hydrate 4-Hydroxyquinaldic Acid4-Hydroxyquinoline-2-carboxylic Acid |
CAS | 492-27-3 |
EINECS | 207-751-5 |
InChI | InChI=1/C10H7NO3.H2O/c12-9-5-8(10(13)14)11-7-4-2-1-3-6(7)9;/h1-5H,(H,11,12)(H,13,14);1H2 |
Molecular Formula | C10H7NO3 |
Molar Mass | 189.17 |
Density | 1.3175 (rough estimate) |
Melting Point | 275°C (dec.)(lit.) |
Boling Point | 324.41°C (rough estimate) |
Flash Point | 267.9°C |
Water Solubility | 8.92g/L(100 ºC) |
Solubility | Soluble in water (partly), hot alcohol, DMSO (75 mM), 0.1 M NaOH (50 mg/ml), and meth |
Vapor Presure | 1.31E-11mmHg at 25°C |
Appearance | Off-white to tan powder. |
Color | White to Gray to Brown |
Merck | 14,5327 |
BRN | 147451 |
pKa | 1.08±0.30(Predicted) |
Storage Condition | Sealed in dry,Room Temperature |
Refractive Index | 1.5400 (estimate) |
MDL | MFCD00006753 |
Use | An antagonist of NMDA and AMPA/kainate receptors |
In vitro study | Kynurenic acid(KYNA) is a metabolite formed by tryptophan through the kynurenine pathway, which can stimulate nerve tissue. It is a non-competitive NMDA type glutamate receptor antagonist. At low concentrations, it inhibits the release of FGF-1 and has a stimulatory effect on the proliferation rate of mouse microglia and human glioblastoma cells. |
In vivo study | Treatment with KYNA(30-100 mg/kg, I. V.) 4 hours before heat shock significantly and dose-dependently reduced the survival time of rats. KYNA can have a protective effect against hypotension, but not hyperthermia during heat stroke. During heat stroke, KYNA attenuates neuronal degeneration and apoptosis in the hypothalamus, as well as apoptosis in the spleen, kidney, liver, and lung. KYNA can up-regulate the level of IL-10 in serum, but down-regulate the levels of TNF-α and ICAM-1. Treatment with KYNA can significantly prevent the occurrence of heat-induced multiple organ damage and inflammation, and has no effect on the caloric value of hyperthermia. Only high concentrations of KYNA can act as neuroprotective by reducing hypoxic or hypoxic-ischemic brain edema in neonatal rats. In adult rats and gerbils, high concentrations of KYNA were also neuroprotective before ischemia induction. KYNA cannot cross the brain blood barrier. |
Hazard Symbols | Xi - Irritant |
Risk Codes | 36/37/38 - Irritating to eyes, respiratory system and skin. |
Safety Description | 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 |
Reference Show more | 1. Li Hui, Cui lanchong, Zhang guolei, Zhang Mengmeng, Jiao Lili, Wu Wei. Quantitative analysis of tryptophan and its metabolites in urine by ultra performance liquid chromatography-tandem mass spectrometry [J]. Chromatography, 2021,39(05):518-525. 2. Zhipg Wang, Hong Jiang, Xujiao Chen, Xinhua Song, Fengjing Xu, Fangchao Chen, zhiuo Mao, Shouhong Gao, wanshen Chen,A rapid and sensitive method for simultaneous determination of eight protein-bound uremic toxins in human serum by UHPLC-MS/MS: A 3. [IF = 3.935] Zhipeng Wang et al."A rapid and sensitive method for simultaneous determination of eight protein-bound uremic toxins in human serum by UHPLC-MS/MS: application in assessing peritoneal dialysis."J Pharmaceut Biomed. 2020 Jul;186:113312 |
EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
biological activity | Kynurenic acid (Quinurenic acid, Kynurenate) is a natural metabolite of tryptophan metabolized through the kynurenine pathway and is a broad-spectrum excitatory amino acid antagonist. It is an antagonist of NMDAR, kainate receptor and AMPA receptor. |
Target | Value |