4-hydroxyquinoline-2-carboxylic acid

• ChemBase ID: 58690
• Molecular Formular: C10H7NO3
• Molecular Mass: 189.16748
• Monoisotopic Mass: 189.04259309
• SMILES: c1ccc2c(c1)c(cc(n2)C(=O)O)O
• Canonical SMILES: OC(=O)c1cc(O)c2c(n1)cccc2
• InChI: 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

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-hydroxyquinoline-2-carboxylic acid
• IUPAC Traditional name: kynurenic acid
• Synonyms: 4-Hydroxyquinoline-2-carboxylic acid; 4-Hydroxyquinoline-2-carboxylic acid; KYNURENIC ACID; 4-Hydroxy-2-quinolinecarboxylic Acid; 4-Hydroxy-quinaldic Acid; 2-Carboxy-4-hydroxyquinoline; 4-Hydroxyquinaldic Acid; 4-Hydroxyquinaldinic Acid; Quinurenic Acid; NSC 58973; Kynurenic acid; 4-Hydroxyquinoline-2-carboxylic acid hydrate; Kynurenic acid; 4-羟基喹啉-2-羧酸水合物; 4-羟基喹啉-2-甲酸; 犬尿喹啉酸

Database IDs

• CAS Number: 492-27-3; 13593-94-7; 345909-35-5
• EC Number: 207-751-5
• MDL Number: MFCD00006753
• Beilstein Number: 147451
• Merck Index: 145327
• PubChem SID: 162063453; 24277986
• PubChem CID: 3845

CALCULATED PROPERTIES

• Acid pKa: 0.963681
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): -0.043512575
• LogD (pH = 7.4): -1.456157
• Log P: 0.7521527
• Molar Refractivity: 48.8444 cm^3
• Polarizability: 19.878067 Å^3
• Polar Surface Area: 70.42 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: 0.1 M NaOH: soluble4 mg/mL; DMSO; DMSO: soluble5 mg/mL; ethanol: soluble; H2O: soluble0.2 mg/mL
• Apperance: Pale Greenish Yellow Solid
• Melting Point: 262-264°C (dec.); 275 °C (dec.)(lit.); 282-283 °C; 283-286°C (dec.); ca 275°C dec.

Safety Information

• Storage Condition: Refrigerator; Room Temperature (15-30°C)
• Storage Warning: IRRITANT
• RTECS: VB2080000
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36; 26-37
• TSCA Listed: false; 否
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Pharmacology Properties

• Gene Information: human ... CHRNA1(1134), CHRNA10(57053), CHRNA2(1135), CHRNA3(1136), CHRNA4(1137), CHRNA5(1138), CHRNA6(8973), CHRNA7(1139), CHRNA9(55584), CHRNB1(1140), CHRNB2(1141), CHRNB3(1142), CHRNB4(1143), GRIA3(2892), GRIA4(2893), GRIK1(2897), GRIK2(2898), GRIK3(2899), GRIK4(2900), GRIK5(2901), GUCA2A(2980), GUCA2B(2981), NGFR(4804), SLC23A2(9962)rat ... Gria1(50592), Grik1(29559), Grin2a(24409)

Product Information

• Purity: ≥98%; 98%
• Empirical Formula (Hill Notation): C10H7NO3

DETAILS

MP Biomedicals - 02102124

Crystalline

Sigma Aldrich - K100

Application
Solutions may be stored at 4 °C for several days.

Sigma Aldrich - K3375

Biochem/physiol Actions
Kynurenic acid is a non-selective antagonist at NMDA and AMPA/kainate receptors; blocks kainic acid neurotoxicity. Kainic acid also blocks nicotinic acetycholine receptors.

Toronto Research Chemicals - K660500

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

REFERENCES

• Wejksza, K., et al.: Pharmacol. Rep., 61, 751 (2009)
• Gohil, V., et al.: Nat. Biotechnol., 28, 249 (2009)
• Di Natale, B., et al.: Toxicol. Sci., 115, 89 (2009)