Pyridine-2,6-dicarboxylic acid

Description

2,6-Pyridinedicarboxylic acid (PDCA) contains two carboxylic groups on each side of the pyridine ring. Both groups form rigid 120° angles with the pyridine. Carboxylic functionality could be complex and bind with metals under certain conditions. Numerous metal?organic frameworks, metal complexes, drugs, and CPs based on PDCA were developed for applications related to gas storage, separation, catalysis, magnetism, and sensing[1]. Shao et al. researched the solubility of PDCA in methanol, ethanol, n-propanol, isopropanol, THF, 1,4-dioxane, acetic acid, formic acid, acetonitrile, ethyl acetate, and toluene. They found that PDCA solubility was the highest in methanol but the lowest in acetonitrile.

Chemical properties

White crystalline powder. Insoluble in ethanol.

Physical properties

Pyridine-2,6-dicarboxylic acid is a solid, soluble in Water: 1%.

The Uses of Pyridine-2,6-dicarboxylic acid

Pyridine-2,6-dicarboxylic acid is used in the preparation of dipicolinato ligated lanthanide and transition metal complexes. It acts as a chelating agent for chromium, zinc, manganese, copper, iron and molybdenum. Its calcium-dipcolinic acid complex is used to protect deoxyribonucleic acid (DNA) from heat denaturation which enhances the DNA stability. It plays an important role as a marker for the effectiveness of sterilization.

Definition

ChEBI: Pyridine-2,6-dicarboxylic acid is a pyridinedicarboxylic acid carrying two carboxy groups at positions 2 and 6. It has a role as a bacterial metabolite. It is a conjugate acid of a dipicolinate(1-).

What are the applications of Application

2,6-Pyridinedicarboxylic acid is an amphoteric polar metabolite produced by many bacterial and fungal species. Prior to its discovery as a microbial metabolite, dipicolinic acid had long been recognised as a chelating agent for many metal ions. Wide distribution of dipicolinic acid among microbes makes it an important dereplication standard in discovery. Dipicolinic acid reaches high concentrations (~10% w/w) in Bacillus endospores aiding heat resistance and is used in laboratories as a marker for the effectiveness of sterilisation.

Preparation

pyridine-2,6-dicarboxylic acid was synthesized by hydrolyzing of ester prepared by coupling of diethyl 4-hydroxypyridine-2,6-dicarboxylate to bis-halohydrocarbon or bis-halide.
Synthesis of Novel Derivatives of Pyridine‐2,6‐dicarboxylic Acid

Synthesis

50 g of acetonitrile, 16.0 g (0.1 mol) of 1, 7-pimelic acid and 0.5 g of aluminum trichloride are added into a 500 ml four-neck flask which is connected with a stirring thermometer and a reflux condenser, chlorine gas is introduced, 30 g of chlorine gas is introduced altogether, the mixture is stirred and reacted for 8 hours at the temperature of 50-55 ℃, the mixture is cooled to 20-25 ℃, the nitrogen gas is blown away for 2 hours, 65 g of 17 wt% ammonia water is added, the mixture is stirred and reacted for 5 hours at the temperature of 70-75 ℃, then the mixture is cooled to 20-25 ℃, 30 g of 30 wt% nitric acid is added, the mixture is stirred and reacted for 4 hours at the temperature of 40-45 ℃, the reaction liquid is added into 200 g of water, the pH value of a hydrochloric acid adjusting system is 2.5-2.0, the filtration and the drying are carried out, 15.0 g of white solid 2, 6-pyridinedicarboxylic acid with.

Synthesis Reference(s)

Synthetic Communications, 22, p. 2691, 1992 DOI: 10.1080/00397919208021669

General Description

This certified eluent concentrate for ion chromatography is traceable by potentiometric titration to NIST Standard Reference Material. It is certified in accordance with ISO Guide 31. All details about exact content, uncertainty, traceability and expiry date are described in the certificate.

References

[1] Xianzhao Shao. Solubility Thermodynamic Modeling and Solubility Parameter of 2,6- Pyridinedicarboxylic Acid in Selected Solvents at Different Temperatures[J]. J. Chem. Eng. Data, 2021. DOI:org/10.1021/acs.jced.1c00200.