Chelidonic acid

Base Information

• Chemical Name: Chelidonic acid
• CAS No.: 99-32-1
• Molecular Formula: C7H4O6
• Molecular Weight: 184.105
• Hs Code.: 29329990
• European Community (EC) Number: 202-749-0
• NSC Number: 3979
• UNII: T33U4W5K6O
• DSSTox Substance ID: DTXSID30243928
• Nikkaji Number: J4.968I
• Wikipedia: Chelidonic_acid
• Wikidata: Q908483
• Metabolomics Workbench ID: 67543
• Mol file: 99-32-1.mol

Synonyms:chelidonic acid

Chemical Property of Chelidonic acid

Chemical Property:

• Melting Point: 265 °C (dec.)(lit.)
• Refractive Index: 1.5600 (estimate)
• Boiling Point: 471.3 °C at 760 mmHg
• PKA: 1.26±0.40(Predicted)
• Flash Point: 204.1 °C
• PSA: 104.81000
• Density: 1.821 g/cm³
• LogP: 0.03620
• Storage Temp.: 2-8°C
• Water Solubility.: 14.3g/L(25 oC)
• XLogP3: -0.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 2
• Exact Mass: 184.00078784
• Heavy Atom Count: 13
• Complexity: 316

Purity/Quality:

4-Oxo-4h-pyran-2,6-dicarboxylicAcid ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=C(OC(=CC1=O)C(=O)O)C(=O)O
• Uses: Chelidonic acid is suitable for use a in homogeneous preparation of native dihydrodipicolinate synthase from pea. It may be used as endocyclic oxygen-containing ligand in the synthesis of aqua[bis(2-pyridylmethyl)amine][chelidonato(1.5-)]-copper(II) chelidonate(0.5-) monohydrate.

Technology Process of Chelidonic acid

There total 7 articles about Chelidonic 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: 88.0%

oxalic acid diethyl ester (95-92-1) + acetone (67-64-1) → chelidonic acid (99-32-1)

Guidance literature:

oxalic acid diethyl ester; acetone; With sodium ethanolate; In ethanol; at 60 ℃; for 1h;

With hydrogenchloride; In ethanol; water; at 50 ℃; for 24h;

DOI:10.1080/00397919908086011

Reference yield: 83.0%

2,4,6-trioxo-heptanedioic acid diethyl ester (68854-18-2) → chelidonic acid (99-32-1)

Guidance literature:

With hydrogenchloride; at 100 ℃; for 20h;

DOI:10.1039/b206782j

Reference yield:

→ chelidonic acid (99-32-1)

Guidance literature:

With sulfuric acid; at 120 - 130 ℃; im geschlossenen Rohr;

upstream raw materials:

2,4,6-trioxo-heptanedioic acid diethyl ester

oxalic acid diethyl ester

acetone

hydrogenchloride

Downstream raw materials:

1-(4-Methoxy-phenyl)-4-oxo-1,4-dihydro-pyridine-2,6-dicarboxylic acid

1-(4-carboxy-phenyl)-4-oxo-1,4-dihydro-pyridine-2,6-dicarboxylic acid

N-p-Carboxyphenyl-4-pyridone-2-carboxylic acid

N-p-Nitrophenyl-4-pyridone-2-carboxylic acid

Refernces

• 1、 Alves, Filipe,Golesorkhi, Bahman,Guénée, Laure,Naseri, Soroush,Nozary, Homayoun,Piguet, Claude,Taarit, Inès. "Ligand-Sensitized Near-Infrared to Visible Linear Light Upconversion in a Discrete Molecular Erbium Complex". supporting information. p. 15326 - 15334. Retrieved 2021/09/30.
• 2、 Rasheed,McDouall,Muryn,Raftery,Vitorica-Yrezabal,Quayle. "The assembly of "s3N"-ligands decorated with an azo-dye as potential sensors for heavy metal ions". . p. 5229 - 5239. Retrieved 2017/04/27.