Chelidamic acid Chemical Properties

Melting point:

265-270 °C

Boiling point:

428.3±45.0 °C(Predicted)

Density 

1.726±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

1 M NH4OH: 50mg/mL, clear to slightly hazy

pka

0.12±0.40(Predicted)

form 

powder

color 

brown

biological source

synthetic (organic)

BRN 

476229

InChI

InChI=1S/C7H5NO5/c9-3-1-4(6(10)11)8-5(2-3)7(12)13/h1-2H,(H,8,9)(H,10,11)(H,12,13)

InChIKey

XTLJJHGQACAZMS-UHFFFAOYSA-N

SMILES

C1(C(O)=O)NC(C(O)=O)=CC(=O)C=1

CAS DataBase Reference

138-60-3(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

HS Code 

29333990

MSDS

• Language:English Provider:Chelidamic acid
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

Chelidamic acid Usage And Synthesis

Chemical Properties

Light yellow powder

Uses

Chelidamic acid hydrate has been used in eluent solution as a complexing additive in high-performance chelation ion chromatography (HPCIC) for speciation of iron. It has also been used as an organic ligand for the polyoxometalate (POM)-based lanthanoid hybrid compounds.

Biochem/physiol Actions

Among the most potent of the tested "conformationally restricted glutamate analogs" as an inhibitor of glutamate decarboxylase.

Synthesis

4-Oxo-1,4-dihydro-2,6-pyridinedicarboxylic acid was synthesized from betulinic acid using a modified literature method. The specific operation was as follows: 425 mL of 30% ammonia solution (containing NH3 41.8 g, 0.21 mol) was slowly added dropwise to the reaction system at 0 °C, and the dropwise addition process was controlled to be completed within 1 hour. After the dropwise addition, the reaction mixture was stirred continuously at room temperature for 48 hours. Upon completion of the reaction, the excess ammonia solution was removed by distillation under reduced pressure. Subsequently, the residue was mixed with 50 mL of water, activated carbon was added and decolorized by refluxing for 15 minutes. After hot filtration, the filtrate was collected and, after being cooled to room temperature, the pH was adjusted with a 37% aqueous hydrochloric acid solution to 1. At this point, a white solid precipitated from the solution, which was collected by filtration, washed several times with cold water, and finally dried under vacuum for 16 h. The target compound, 4-oxo-1,4-dihydro-2,6-pyridinedicarboxylic acid (13), was obtained as a white solid in a yield of 42 g with 98% yield.

Advantages

Chelidamic acid (1,4-dihydro-4-oxopyridine-2,6- dicarboxylic acid, CDA) is an organic material with great potential for accepting alkaline ions. It could be used as the anode material in LIBs. The new materials offer high capacity, superior cycle retention, favourable rate capability, and interesting electrochemical behaviours[1].

References

[1] Fu-Ming Wang*. “Synthesis and Characterization of Chelidonic Acid and Chelidamic Acid as Organic Anode Materials for Energy Storage.” ACS Sustainable Chemistry & Engineering 9 36 (2021): 12286–12299.

Chelidamic acid(138-60-3)Related Product Information

• Chelidonic acid monohydrate
• Chelidonic acid
• Chelidamic acid
• 5-HYDROXYPYRIDINE-3,4-DICARBOXYLIC ACID METHYL ESTER,5-Hydroxypyridine-3,4-dicarboxylic acid 4-methyl ester
• CHELIDAMIC ACID MONOHYDRATE, 98
• Chrysene
• 4-Methoxypyridine-2,6-dicarboxylic acid
• Diethyl 4-ethoxy-2,6-pyridinedicarboxylate
• 6-Methyl-5-hydroxypyridine-3,4-dicarboxylic acid
• Dimethyl 4-methoxy-2,6-Pyridinedicarboxylate
• 5-Hydroxypyridine-2,3-dicarboxylic acid dimethyl ester
• 4-HYDROXYPYRIDINE-2,6-DICARBOXYLIC ACID MONOHYDRATE,CHELIDAMIC ACID MONOHYDRATE
• 2-Methyl-6-hydroxypyridine-3,4-dicarboxylic acid dimethyl ester
• 6-Methyl-5-hydroxypyridine-2,3-dicarboxylic acid dimethyl ester
• 4-Ethoxy-2,6-pyridinedicarboxylic acid
• 6-Hydroxypyridine-3,4-dicarboxylic acid dimethyl ester
• Dibutyl 4-butoxy-2,6-pyridinedicarboxylate
• 4-Butoxy-2,6-pyridinedicarboxylic acid