3-Carboxylato-1-(2-hydroxyethyl)pyridinium
[CAS# 52578-48-0]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyridine compound >> Pyridine derivative
• Name: 3-Carboxylato-1-(2-hydroxyethyl)pyridinium
• Synonyms: 1-(2-hydroxyethyl)pyridin-1-ium-3-carboxylate
• Molecular Formula: C₈H₉NO₃
• Molecular Weight: 167.16
• CAS Registry Number: 52578-48-0
• EC Number: 258-016-0
• SMILES: C1=CC(=C[N+](=C1)CCO)C(=O)[O-]

Discovory and Applicatios

3-Carboxylato-1-(2-hydroxyethyl)pyridinium is a zwitterionic compound derived from a substituted pyridine framework. It consists of a pyridinium ring bearing a 2-hydroxyethyl substituent on the nitrogen atom and a carboxylate group positioned at the third carbon of the ring. This molecular structure results in both a positively charged quaternized nitrogen and a negatively charged carboxylate group within the same molecule, giving it amphoteric and zwitterionic characteristics.

The design of such compounds makes them particularly useful in biochemical and pharmaceutical research. The presence of a pyridinium core provides structural rigidity and a delocalized positive charge that can participate in various ionic interactions. The 2-hydroxyethyl side chain contributes additional hydrophilicity and the capacity to form hydrogen bonds, while the carboxylate group contributes to the compound's overall solubility and ionic behavior in aqueous environments. The zwitterionic nature of 3-carboxylato-1-(2-hydroxyethyl)pyridinium enhances its potential as a buffer-like agent in biological systems or as a structural scaffold in the design of ionic liquids or water-soluble materials.

Chemically, the formation of this compound can be achieved by quaternization of 2-hydroxyethylpyridine followed by functionalization at the 3-position of the pyridine ring to introduce a carboxyl group. The resulting structure is stable under physiological conditions and demonstrates compatibility with a variety of biological media. Its ability to maintain charge separation within a single molecule without leading to precipitation or aggregation makes it favorable for applications requiring biocompatible ionic species.

In medicinal chemistry, derivatives of pyridinium compounds have been explored for their antimicrobial, anti-inflammatory, and enzyme-inhibitory activities. While 3-carboxylato-1-(2-hydroxyethyl)pyridinium itself may not exhibit potent bioactivity, its chemical architecture makes it a candidate for modification into active pharmacophores or for use as a functional excipient that can enhance the solubility or delivery of therapeutic agents.

This compound can also play a role in the development of zwitterionic surfactants or stabilizers for nanoparticle formulations. The distinct ionic groups allow for interaction with both hydrophobic and hydrophilic environments, contributing to the stabilization of colloidal systems or the formation of micellar structures. Additionally, its structural features are useful in analytical chemistry, where such zwitterions may serve as standards, ion-pairing agents, or functional groups in ion chromatography and capillary electrophoresis.

In polymer science, zwitterionic monomers similar to 3-carboxylato-1-(2-hydroxyethyl)pyridinium are being investigated for the synthesis of antifouling materials and hydrogels with high water retention and resistance to protein adsorption. These materials are particularly useful in biomedical devices, where non-specific binding and biofouling are major challenges. The introduction of such functional groups can also enhance the ionic conductivity and thermal stability of polymer electrolytes used in batteries and fuel cells.

Overall, 3-carboxylato-1-(2-hydroxyethyl)pyridinium is a versatile chemical entity whose combination of ionic characteristics and hydrophilic substituents supports a wide range of potential applications in chemical, biological, and material sciences.

References

1998. Novel Betaines from the Marine Sponge Agelas dispar. Journal of Natural Products, 61(8).
DOI: 10.1021/np980157t

2023. The LOTUS Initiative for Open Natural Products Research: frozen dataset union wikidata (with metadata).
DOI: 10.5281/zenodo.5794106