Surf Wiki
Save to docs
general/2-pyridyl-compounds

From Surf Wiki (app.surf) — the open knowledge base

Picolinic acid

Pyridine-2-carboxylic acid; bidentate chelating agent

Picolinic acid

Pyridine-2-carboxylic acid; bidentate chelating agent

Picolinic acid is an organic compound with the formula . It is a derivative of pyridine with a carboxylic acid (COOH) substituent at the 2-position. It is an isomer of nicotinic acid and isonicotinic acid, which have the carboxyl side chain at the 3- and 4-positions, respectively. It is a white solid although impure samples can appear tan. The compound is soluble in water.

Production

On a commercial scale, picolinic acid is produced by ammoxidation of 2-picoline followed by hydrolysis of the resulting nitrile: : : It is also produced by oxidation of picoline with nitric acid. :[[File:Oxidation of 2-picoline.png|350px]] In the laboratory, picolinic acid is formed from 2-methylpyridine by oxidation with potassium permanganate (KMnO4).

Reactions

Structure of Zn(picolinate)<sub>2</sub>(H<sub>2</sub>O)<sub>2</sub>.

Hydrogenation of picolinic acid gives piperidine-2-carboxylic acid, a precursor to the drug Mepivacaine.

Picolinic acid is a bidentate chelating agent of elements such as chromium, zinc, manganese, copper, iron, and molybdenum in the human body.

It is a substrate in the Mitsunobu reaction. In the Hammick reaction, picolinic acid reacts with ketones to give pyridine-2-carbonols: :

Biosynthesis

Picolinic acid is a catabolite of the amino acid tryptophan through the kynurenine pathway. Its function is unclear, but it has been implicated in a variety of neuroprotective, immunological, and anti-proliferative effects. In addition, it is suggested to assist in the absorption of zinc(II) ions and other divalent or trivalent ions through the small intestine.

Picolinates

Salts of picolinic acid (picolinates) include:

  • Chromium(III) picolinate
  • Zinc picolinate

References

References

  1. Lide, DR. "CRC Handbook of Chemistry and Physics, Internet Version 2005, http://hbcpnetbase.com, CRC Press, Boca Raton, Florida, 2005".
  2. (2007). "Pyridine and Pyridine Derivatives".
  3. (1940). "Picolinic Acid Hydrochloride". Organic Syntheses.
  4. Harold Hart, Leslie E. Craine, David J. Hart, Christopher M. Hadad; Nicole Kindler. (2007). "'Organische Chemie 3. Auflage". Wiley-VCH.
  5. (1969). "The Crystal Structure of Zinc Picolinate Tetrahydrate, Zn(C6H4O2N)2(H2O)4". Acta Chemica Scandinavica.
  6. (2015). "Bidentate, Monoanionic Auxiliary-Directed Functionalization of Carbon–Hydrogen Bonds". Accounts of Chemical Research.
  7. Fuchs, Philip L.. (2013-07-29). "Catalytic Oxidation Reagents". Wiley Inc..
  8. (December 2012). "The kynurenine pathway in neurodegenerative diseases: mechanistic and therapeutic considerations". J Neurol Sci.
  9. Evans, Gary. (1982). "The Role of Picolinic Acid in Metal Metabolism". Harwood Academic Publishers.
Info: Wikipedia Source

This article was imported from Wikipedia and is available under the Creative Commons Attribution-ShareAlike 4.0 License. Content has been adapted to SurfDoc format. Original contributors can be found on the article history page.

2-pyridyl-compounds glycine-receptor-agonists chelating-agents aromatic-acids
Want to explore this topic further?

Ask Mako anything about Picolinic acid — get instant answers, deeper analysis, and related topics.

Research with Mako

Free with your Surf account

Content sourced from Wikipedia, available under CC BY-SA 4.0.

This content may have been generated or modified by AI. CloudSurf Software LLC is not responsible for the accuracy, completeness, or reliability of AI-generated content. Always verify important information from primary sources.

Report