6-Hydroxynicotinic acid

Base Information

• Chemical Name: 6-Hydroxynicotinic acid
• CAS No.: 5006-66-6
• Deprecated CAS: 4588-15-2
• Molecular Formula: C6H5NO3
• Molecular Weight: 139.111
• Hs Code.: 2933.39
• European Community (EC) Number: 225-682-9
• NSC Number: 53377,35054,8620
• UNII: 8PLJ71N310
• DSSTox Substance ID: DTXSID0057754
• Nikkaji Number: J208I
• Wikidata: Q27098413
• Metabolomics Workbench ID: 38187
• ChEMBL ID: CHEMBL95293
• Mol file: 5006-66-6.mol

Synonyms:6-hydroxynicotinic acid

Chemical Property of 6-Hydroxynicotinic acid

Chemical Property:

• Appearance/Colour: Off-white powder
• Vapor Pressure: 5.81E-07mmHg at 25°C
• Melting Point: 300 °C(lit.)
• Refractive Index: 1.5423 (estimate)
• Boiling Point: 384 °C at 760 mmHg
• PKA: 3.80±0.50(Predicted)
• Flash Point: 186 °C
• PSA: 70.16000
• Density: 1.451 g/cm³
• LogP: 0.07310
• Storage Temp.: Refrigerator
• Solubility.: DMSO (Slightly), Methanol (Slightly, Heated)
• XLogP3: -0.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 139.026943022
• Heavy Atom Count: 10
• Complexity: 239

Purity/Quality:

99% ^*data from raw suppliers

6-Hydroxynicotinic Acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Nitrogen Compounds -> Pyridines
• Canonical SMILES: C1=CC(=O)NC=C1C(=O)O
• Uses: 6-Hydroxynicotinic acid is used as building block in chemical synthesis. Nicotinic Acid derivative, found in fruit hypanthium. Metabolite of nicotinamide. Stimulates adrenocortical secretion

Technology Process of 6-Hydroxynicotinic acid

There total 26 articles about 6-Hydroxynicotinic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.7%

nicotinic acid (59-67-6) → 6-hydroxy-3-pyridinecarboxylic acid (5006-66-6)

Guidance literature:

at 35 ℃; for 45h; Product distribution; production by resting cells of Pseudomonas fluorescens TN₅; effects of aeration; optimization of culture medium; effect molybdenum and iron ions and nicotinic acid as inducer on the formation of the hydroxylated enzyme; pH 6.5;

DOI:10.1271/bbb.58.665

Reference yield: 79.0%

triethylamine (121-44-8) → 6-hydroxy-3-pyridinecarboxylic acid (5006-66-6)

Guidance literature:

With potassium hydroxide; acetic anhydride; In tetrachloromethane;

Reference yield: 62.0%

Nicotinic acid N-oxide (2398-81-4) → 6-hydroxy-3-pyridinecarboxylic acid (5006-66-6) + 2-hydroxy-3-carboxypyridine (609-71-2) + 3-acetoxy-4-aza-3-methyl-1(3H)-isobenzofuranone 4-oxide (111068-01-0)

Guidance literature:

With acetic anhydride; for 6h; Heating;

DOI:10.3987/R-1987-05-1263

upstream raw materials:

2-Pyridone

methylammonium carbonate

6-fluoronicotinic acid

6-bromonicotinic acid

Downstream raw materials:

methyl 6-hydroxynicotinate

ethyl 6-hydroxypyridine-3-carboxylate

1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid

2-Pyridone

Refernces

• 1、 Nagasawa,Hurh,Yamane. "Production of 6-hydroxynicotinic acid from nicotinic acid by resting cells of Pseudomonas fluorescens TN5". . p. 665 - 668. Retrieved 1994.
• 2、 Coleman, Tom,Chao, Rebecca R.,Bruning, John B.,De Voss, James J.,Bell, Stephen G.. "CYP199A4 catalyses the efficient demethylation and demethenylation of para-substituted benzoic acid derivatives". . p. 52007 - 52018. Retrieved 2015/06/25.