5-Hydroxy-4-oxo-4H-pyran-2-carboxylic acid

Base Information

• Chemical Name: 5-Hydroxy-4-oxo-4H-pyran-2-carboxylic acid
• CAS No.: 499-78-5
• Molecular Formula: C6H4O5
• Molecular Weight: 156.095
• Hs Code.: 2932999099
• European Community (EC) Number: 207-891-7
• DSSTox Substance ID: DTXSID4060103
• Nikkaji Number: J6.181F
• Wikidata: Q81989056
• ChEMBL ID: CHEMBL177875
• Mol file: 499-78-5.mol

Synonyms:5-hydroxy-gamma-pyrone-2-carboxylic acid;comenic acid;potassium comenate

Chemical Property of 5-Hydroxy-4-oxo-4H-pyran-2-carboxylic acid

Chemical Property:

• Vapor Pressure: 7.71E-09mmHg at 25°C
• Melting Point: 284-294 °C
• Refractive Index: 1.66
• Boiling Point: 420.7 °C at 760 mmHg
• Flash Point: 187.7 °C
• PSA: 87.74000
• Density: 1.819 g/cm³
• LogP: 0.04360
• Water Solubility.: 5.1g/L(25 oC)
• XLogP3: -0.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 1
• Exact Mass: 156.00587322
• Heavy Atom Count: 11
• Complexity: 273

Purity/Quality:

99% ^*data from raw suppliers

ComenicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=C(OC=C(C1=O)O)C(=O)O
• Uses: 5-hydroxy-4-oxo-4H-pyran-2-carboxylic acid can be used in the regenerative anti-inflammatory composition Building block for an intramolecular olefin-α-pyrone cycloaddition providing the colchicine ring skeleton.

Technology Process of 5-Hydroxy-4-oxo-4H-pyran-2-carboxylic acid

There total 11 articles about 5-Hydroxy-4-oxo-4H-pyran-2-carboxylic 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: 93.0%

5-(benzyloxy)-4-oxo-4H-pyran-2-carboxylic acid (1219-33-6) → comenic acid (499-78-5)

Guidance literature:

With palladium on activated charcoal; hydrogen; In ethanol; at 20 ℃; for 1h;

DOI:10.1016/j.bioorg.2019.103550

Reference yield:

5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one (501-30-4,123712-78-7) → comenic acid (499-78-5)

Guidance literature:

Multi-step reaction with 3 steps

1: caesium carbonate / N,N-dimethyl-formamide / 0.5 h / 70 °C

2: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; sodium hydrogencarbonate / water; dichloromethane / 2 h / 0 °C

3: sodium iodide; chloro-trimethyl-silane / acetonitrile / 5.5 h / 70 °C / Inert atmosphere

With chloro-trimethyl-silane; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; sodium hydrogencarbonate; caesium carbonate; sodium iodide; In dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1080/00304948.2018.1525990

Reference yield:

5-benzyloxy-2-hydroxymethyl-4H-pyran-4-one (15771-06-9) → comenic acid (499-78-5)

Guidance literature:

Multi-step reaction with 2 steps

1: chromium(VI) oxide; sulfuric acid / water; acetone / 3.5 h / 20 °C / Cooling with ice

2: hydrogen; palladium on activated charcoal / ethanol / 1 h / 20 °C

With chromium(VI) oxide; sulfuric acid; palladium on activated charcoal; hydrogen; In ethanol; water; acetone;

DOI:10.1016/j.bioorg.2019.103550

upstream raw materials:

3,4-dioxo-3,4-dihydro-2H-pyran-2,6-dicarboxylic acid

hydrogenchloride

water

hydrogen iodide

Downstream raw materials:

5-benzoyloxy-4-oxo-4H-pyran-2-carboxylic acid

5-benzoyloxy-4-oxo-4H-pyran-2-carboxylic acid ethyl ester

5-methoxy-4-oxo-4H-pyran-2-carboxylic acid

2-Carboxy-5-hydroxy-1-methyl-4-pyridon

Refernces

• 1、 Güntzel, Paul,Forster, Leonard,Schollmayer, Curd,Holzgrabe, Ulrike. "A Convenient Preparation of Carboxy-γ-pyrone Derivatives: Meconic Acid and Comenic Acid". . p. 512 - 516. Retrieved 2019/01/10.