5-Hydroxy-6-methylpyridine-3,4-dicarboxylic acid

Base Information

• Chemical Name: 5-Hydroxy-6-methylpyridine-3,4-dicarboxylic acid
• CAS No.: 479-30-1
• Molecular Formula: C8H7 N O5
• Molecular Weight: 197.147
• UNII: 60H2Q57ICL
• DSSTox Substance ID: DTXSID60331488
• Nikkaji Number: J102.235K
• Wikidata: Q27102743
• Metabolomics Workbench ID: 39107
• Mol file: 479-30-1.mol

Synonyms:Ichiba acid;479-30-1;5-hydroxy-6-methylpyridine-3,4-dicarboxylic acid;5-Hydroxy-6-methyl-3,4-pyridinedicarboxylic acid;3,4-Pyridinedicarboxylic acid, 5-hydroxy-6-methyl-;3-Hydroxy-2-methylpyridine-4,5-dicarboxylate;60H2Q57ICL;3,4-Pyridinedicarboxylicacid, 5-hydroxy-6-methyl-;UNII-60H2Q57ICL;SCHEMBL11562679;CHEBI:17978;DTXSID60331488;C04604;5-hydroxy-6-methylpyridine-3,4-dicarboxylicacid;2-methyl-3-hydroxy-4,5-pyridinedicarboxylic acid;5-Hydroxy-6-methyl-3,4-pyridinedicarboxylic acid #;Q27102743

Chemical Property of 5-Hydroxy-6-methylpyridine-3,4-dicarboxylic acid

Chemical Property:

• PSA: 107.72000
• LogP: 0.49200
• XLogP3: 0.5
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 2
• Exact Mass: 197.03242232
• Heavy Atom Count: 14
• Complexity: 254

Purity/Quality:

99% ^*data from raw suppliers

5-Hydroxy-6-methyl-3,4-pyridinedicarboxylicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=NC=C(C(=C1O)C(=O)O)C(=O)O
• Uses: 5-Hydroxy-6-methyl-3,4-pyridinedicarboxylic Acid is used in studies to identify 4-pyridoxic acid dehydrogenase gene in pyridoxine catabolism of Mesorhizobium loti MAFF303099.

Technology Process of 5-Hydroxy-6-methylpyridine-3,4-dicarboxylic acid

There total 19 articles about 5-Hydroxy-6-methylpyridine-3,4-dicarboxylic 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:

3-amino-2-methylpyridin-4,5-dicarboxylic acid (5442-82-0) → 5-hydroxy-6-methyl-pyridine-3,4-dicarboxylic acid (479-30-1)

Guidance literature:

With sulfuric acid; sodium nitrite; at 90 - 95 ℃;

DOI:10.1021/ja01556a021

Reference yield:

methyl 3-cyano-2-hydroxy-6-methyl-isonicotinate (18724-73-7) → 5-hydroxy-6-methyl-pyridine-3,4-dicarboxylic acid (479-30-1)

Guidance literature:

Multi-step reaction with 6 steps

1: urea; acetic acid anhydride; HNO₃

2: chlorobenzene; PCl₅

3: iron; acetic acid

4: palladium/BaCO₃; ethanol / Hydrogenation

5: concentrated aqueous HCl

6: aqueous H₂SO₄; aqueous NaNO₂ / 90 - 95 °C

With hydrogenchloride; palladium-barium carbonate; ethanol; phosphorus pentachloride; sulfuric acid; nitric acid; acetic anhydride; iron; acetic acid; chlorobenzene; urea; sodium nitrite;

DOI:10.1021/ja01556a021

Reference yield:

3-cyano-2-hydroxy-6-methyl-5-nitro-isonicotinic acid methyl ester (98590-00-2) → 5-hydroxy-6-methyl-pyridine-3,4-dicarboxylic acid (479-30-1)

Guidance literature:

Multi-step reaction with 5 steps

1: chlorobenzene; PCl₅

2: iron; acetic acid

3: palladium/BaCO₃; ethanol / Hydrogenation

4: concentrated aqueous HCl

5: aqueous H₂SO₄; aqueous NaNO₂ / 90 - 95 °C

With hydrogenchloride; palladium-barium carbonate; ethanol; phosphorus pentachloride; sulfuric acid; iron; acetic acid; chlorobenzene; sodium nitrite;

DOI:10.1021/ja01556a021

upstream raw materials:

3-amino-2-methylpyridin-4,5-dicarboxylic acid

5-hydroxy-6-methyl-pyridine-3,4-dicarboxylic acid dimethyl ester

5-hydroxy-6-methylpyridine-3,4-dicarboxylic acid diethyl ester

methyl 3-cyano-2-hydroxy-6-methyl-isonicotinate

Downstream raw materials:

5-benzyloxy-6-methyl-pyridine-3,4-dicarboxylic acid dibenzyl ester

5-hydroxy-6-methyl-3,4-pyridinedimethanol

5-hydroxy-6-methyl-pyridine-3,4-dicarboxylic acid dimethyl ester

4,5-bis-hydroxymethyl-3-methoxy-2-methyl-pyridine