Meconic acid

Base Information

• Chemical Name: Meconic acid
• CAS No.: 497-59-6
• Molecular Formula: C7H4 O7
• Molecular Weight: 200.105
• European Community (EC) Number: 207-848-2
• NSC Number: 805
• UNII: V502I79516
• DSSTox Substance ID: DTXSID2060096,DTXSID20901328
• Nikkaji Number: J6.102F
• Wikipedia: Meconic_acid
• Wikidata: Q421116
• Metabolomics Workbench ID: 46159
• ChEMBL ID: CHEMBL109516
• Mol file: 497-59-6.mol

Synonyms:meconic acid

Chemical Property of Meconic acid

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 120°C (rough estimate)
• Refractive Index: 1.4455 (estimate)
• Boiling Point: 353.8°Cat760mmHg
• PKA: 0.60±0.40(Predicted)
• Flash Point: 149.8°C
• PSA: 125.04000
• Density: 2.043g/cm³
• LogP: -0.25820
• Storage Temp.: Hygroscopic, Refrigerator, under inert atmosphere
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• Water Solubility.: 8.4g/L(25 oC)
• XLogP3: 0
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 2
• Exact Mass: 199.99570246
• Heavy Atom Count: 14
• Complexity: 387

Purity/Quality:

99%, ^*data from raw suppliers

MeconicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=C(OC(=C(C1=O)O)C(=O)O)C(=O)O
• Uses: 3-hydroxy-4-oxopyran-2,6-dicarboxylic acid has anti inflammatory and antibacterial action. Meconic Acid has been used to detect the presence of opium . Meconic Acid has anti inflammatory and antibacterial action. Meconic Acid has been used to detect the presence of opium .

Technology Process of Meconic acid

There total 5 articles about Meconic 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: 76.0%

3-benzyloxy-2,6-dicarboxy-γ-pyrone → meconic acid (497-59-6)

Guidance literature:

With chloro-trimethyl-silane; sodium iodide; In acetonitrile; at 70 ℃; for 4h; Inert atmosphere;

DOI:10.1080/00304948.2018.1525990

Reference yield: 30.0%

2,6-dihydroxymethyl-3-hydroxy-4-pyrone (2029-49-4) → meconic acid (497-59-6)

Guidance literature:

With sodium hydroxide; palladium on activated charcoal; air; for 144h; Ambient temperature;

DOI:10.1021/ja990402a

Reference yield:

5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one (501-30-4,123712-78-7) → meconic acid (497-59-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 71 percent / aq. NaOH / methanol / 48 h

2: 30 percent / aq. NaOH, 10 percent Pd/C, air / 144 h / Ambient temperature

With sodium hydroxide; palladium on activated charcoal; air; In methanol;

DOI:10.1021/ja990402a

upstream raw materials:

2,6-dihydroxymethyl-3-hydroxy-4-pyrone

5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one

3-(benzyloxy)-2,6-bis(hydroxymethyl)-4H-pyran-4-one

Refernces

• 1、 Lovell, Scott,Subramony, Paramjeet,Kahr, Bart. "Poppy acid: Synthesis and crystal chemistry". . p. 7020 - 7025. Retrieved 2007/10/03.