3-Hydroxypicolinic acid

3-Hydroxypicolinic acid is an organic compound that belongs to the class of substances known as pyridinecarboxylic acids. It is a derivative of pyridine, with a hydroxyl group (-OH) attached to the third carbon in the ring and a carboxylic acid group (-COOH) attached to the adjacent carbon. The chemical formula of 3-hydroxypicolinic acid is C₆H₅NO₃.

Structure and Properties

3-Hydroxypicolinic acid features a six-membered pyridine ring, which is a heterocyclic aromatic ring containing one nitrogen atom. The presence of both the hydroxyl and carboxylic acid functional groups on the ring structure significantly influences its chemical behavior, making it both a hydroxy acid and a pyridinecarboxylic acid. This compound is characterized by its ability to form hydrogen bonds due to the hydroxyl group, which also affects its solubility in water and other polar solvents.

Synthesis

The synthesis of 3-hydroxypicolinic acid can be achieved through several methods, including the hydroxylation of picolinic acid or from the oxidation of 3-hydroxymethylpyridine. These methods involve complex reactions that require precise conditions and catalysts to ensure the correct placement of the hydroxyl group on the pyridine ring.

Applications

3-Hydroxypicolinic acid finds applications in various fields, including organic synthesis, where it serves as a building block for the synthesis of more complex molecules. In biochemistry, it is used as a chelating agent for the analysis of metal ions by mass spectrometry, particularly in the technique known as Matrix-Assisted Laser Desorption/Ionization (MALDI) mass spectrometry. This application takes advantage of its ability to absorb laser energy and assist in the ionization of analyte molecules without causing their fragmentation.

Safety and Toxicology

The safety and toxicological profile of 3-hydroxypicolinic acid is an important consideration, especially in its use in laboratory and industrial settings. While specific data may vary, standard safety measures should be observed when handling this chemical, including the use of personal protective equipment (PPE) and adherence to material safety data sheet (MSDS) guidelines.

See Also

• Pyridine
• Carboxylic acid
• Matrix-Assisted Laser Desorption/Ionization