6-hydroxypyridine-3-carboxylic acid

• ChemBase ID: 11751
• Molecular Formular: C6H5NO3
• Molecular Mass: 139.1088
• Monoisotopic Mass: 139.02694303
• SMILES: c1(ccc(cn1)C(=O)O)O
• Canonical SMILES: Oc1ccc(cn1)C(=O)O
• InChI: InChI=1S/C6H5NO3/c8-5-2-1-4(3-7-5)6(9)10/h1-3H,(H,7,8)(H,9,10)
• InChIKey: BLHCMGRVFXRYRN-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 6-hydroxypyridine-3-carboxylic acid
• IUPAC Traditional name: 6-hydroxynicotinic acid
• Synonyms: 1,6-Dihydro-6-oxo-nicotinic Acid; 2-Hydroxy-5-carboxypyridine; 5-Carboxy-2-pyridone; 6-Hydroxyniacin; 6-Oxo-1,6-dihydro-pyridine-3-carboxylic acid; NSC 35054; NSC 53377; NSC 8620; 6-Hydroxy Nicotinic Acid; 6-Hydroxynicotinic acid; 2-Hydroxypyridine-5-carboxylic acid; 6-Hydroxypyridine-3-carboxylic acid; 6-Hydroxynicotinic acid 98%; 6-HYDROXYNOCOTINIC ACID; 2-Hydroxy-5-pyridinecarboxylic acid; 6-Hydroxynicotinic acid; 6-Hydroxypyridine-3-carboxylic acid; 1,6-Dihydro-6-oxo-3-pyridinecarboxylic Acid; 6-Hydroxynicotinic acid; 2-羟基-5-吡啶甲酸; 6-羟基烟酸; 6-羟基吡啶-3-羧酸; 6-羟基烟酸

Database IDs

• CAS Number: 15864-85-4; 5006-66-6
• EC Number: 225-682-9
• MDL Number: MFCD00006277
• Beilstein Number: 115991; 472182
• PubChem SID: 160975058; 24847874; 24879632
• PubChem CID: 72924

CALCULATED PROPERTIES

• Acid pKa: 3.7713268
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): -1.027174
• LogD (pH = 7.4): -2.571898
• Log P: 0.7040485
• Molar Refractivity: 33.4517 cm^3
• Polarizability: 12.466652 Å^3
• Polar Surface Area: 70.42 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Pale Yellow Solid
• Melting Point: >300 °C(lit.); >300°C; 302-308 °C; 303-305°C (dec.); 314-316°C

Safety Information

• Storage Condition: Refrigerator; Room Temperature (15-30°C)
• Storage Warning: IRRITANT; Irritant
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36; 26-37
• TSCA Listed: true; 是
• 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

Product Information

• Purity: ~98%; ≥98.0% (HPLC); 97%; 98%
• Grade: analytical standard; purum
• Impurities: ≤1.0% water
• Empirical Formula (Hill Notation): C6H5NO3

DETAILS

MP Biomedicals - 02102014

Purity: ~98%
Stimulates adrenocortical secretion^1 .
Also a metabolite of nicotinamide^2 .

MP Biomedicals - 05208580

MP Biomedicals Rare Chemical collection

Sigma Aldrich - 128759

Application
Employed in the synthesis of retinoids.1
Packaging
25, 100 g in poly bottle
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. 128759.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Toronto Research Chemicals - H948545

Nicotinic Acid derivative, found in fruit hypanthium.

REFERENCES

• Biochem. Med. , 2 : 438, (1969).
• J. Biol. Chem. , 244 : 3277, (1969).
• Stetinova, V., et al.: Exper. Toxicol. Pathol., 52, 473 (2000)
• Vajragupta, O., et al.: Bioorg. Med. Chem., 11, 2329 (2000)
• Paternoster, T., et al.: J. Agric. Food Chem., 57, 10038 (2000)
• Ohta, T., et al.: Toxicol. Pathol., 37, 521 (2000)