Picolinic acid

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Pyridine-2-carboxylic acid; bidentate chelating agent

title: "Picolinic acid" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["2-pyridyl-compounds", "glycine-receptor-agonists", "chelating-agents", "aromatic-acids"] description: "Pyridine-2-carboxylic acid; bidentate chelating agent" topic_path: "general/2-pyridyl-compounds" source: "https://en.wikipedia.org/wiki/Picolinic_acid" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

::summary Pyridine-2-carboxylic acid; bidentate chelating agent ::

|Verifiedimages = changed |Watchedfields = changed |verifiedrevid = 464206292 |ImageFile1_Ref = |ImageFile1 =Picolinic acid.svg |ImageSize1 =180px |ImageFile2 = |ImageSize2 =180px |PIN = Pyridine-2-carboxylic acid |OtherNames = Picolinic acid |Section1={{Chembox Identifiers |ChemSpiderID_Ref = |ChemSpiderID = 993 |InChI = 1/C6H5NO2/c8-6(9)5-3-1-2-4-7-5/h1-4H,(H,8,9) |InChIKey = SIOXPEMLGUPBBT-UHFFFAOYAC |ChEMBL_Ref = |ChEMBL = 72628 |StdInChI_Ref = |StdInChI = 1S/C6H5NO2/c8-6(9)5-3-1-2-4-7-5/h1-4H,(H,8,9) |StdInChIKey_Ref = |StdInChIKey = SIOXPEMLGUPBBT-UHFFFAOYSA-N |CASNo_Ref = |CASNo =98-98-6 |UNII_Ref = |UNII = QZV2W997JQ |PubChem =1018 |ChEBI_Ref = |ChEBI = 28747 |SMILES = c1ccnc(c1)C(=O)O |Section2={{Chembox Properties |C=6 | H=5 | N=1 | O=2 |Appearance = White solid |MeltingPtC = 136 to 138 |Density = 1.526 g/cm³ |Solubility = Slightly soluble (0.41%) in water

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

::figure[src="https://upload.wikimedia.org/wikipedia/commons/5/51/CSD_CIF_ZNPICH01.jpg" caption="Structure of Zn(picolinate)2(H2O)2."] ::

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:

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.

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2-pyridyl-compoundsglycine-receptor-agonistschelating-agentsaromatic-acids