4,8-dihydroxyquinoline-2-carboxylic acid

• ChemBase ID: 102850
• Molecular Formular: C10H7NO4
• Molecular Mass: 205.16688
• Monoisotopic Mass: 205.03750771
• SMILES: OC(=O)c1cc(O)c2cccc(O)c2n1
• Canonical SMILES: OC(=O)c1cc(O)c2c(n1)c(O)ccc2
• InChI: InChI=1S/C10H7NO4/c12-7-3-1-2-5-8(13)4-6(10(14)15)11-9(5)7/h1-4,12H,(H,11,13)(H,14,15)
• InChIKey: FBZONXHGGPHHIY-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4,8-dihydroxyquinoline-2-carboxylic acid
• IUPAC Traditional name: xanthurenic acid
• Synonyms: 4,8-Dihydroxyquinaldic acid; 4,8-Dihydroxyquinoline-2-carboxylic acid; XANTHURENIC ACID; 4,8-DIHYDROXYGUINALDIC ACID; Xanthurenic acid; 4,8-Dihydroxy-2-quinolinecarboxylic Acid; NSC 401570; Xanthuric acid; Xanthurenate; 8-Hydroxykynurenic acid; 4,8-二羟基喹啉-2-甲酸; 4,8-二羟基喹啉甲酸; 黄尿酸

Database IDs

• CAS Number: 59-00-7
• EC Number: 200-410-1
• MDL Number: MFCD00006754
• Beilstein Number: 185954
• PubChem SID: 24893378; 24890171; 162091233
• PubChem CID: 5699
• Wikipedia Title: Xanthurenic_acid

CALCULATED PROPERTIES

• Acid pKa: 1.1175392
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -0.32295325
• LogD (pH = 7.4): -1.7002906
• Log P: 0.07666184
• Molar Refractivity: 50.8253 cm^3
• Polarizability: 20.50828 Å^3
• Polar Surface Area: 90.65 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Insoluble in water
• Apperance: Yellow crystals
• Melting Point: 286; 286°C; 297-298 °C (dec.)(lit.)

Safety Information

• Storage Condition: Room Temperature (15-30°C)
• RTECS: UZ9275000
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: ~99%; ≥95.0% (HPLC); 96%
• Grade: purum
• Empirical Formula (Hill Notation): C10H7NO4

DETAILS

MP Biomedicals - 05203053

MP Biomedicals Rare Chemical collection

MP Biomedicals - 02103297

Crystalline Purity: ~99%

Sigma Aldrich - D120804

Packaging
1, 5 g in glass bottle

Sigma Aldrich - 95570

Application
Metabolic intermediate which accumulates in vitamin B6 deficiency

Toronto Research Chemicals - X743500

Excreted by pyridoxine-deficient animals after the ingestion of tryptophan.

REFERENCES

• Aquilina, J., et al.: Biochemistry, 39, 16176 (2000)
• Roberts, J., et al.: Photochem. Photobiol., 74, 740 (2000)