Picolinic acid
Names
Preferred IUPAC name
Pyridine-2-carboxylic acid
Other names
Picolinic acid
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.002.472 Edit this at Wikidata
UNII
  • InChI=1S/C6H5NO2/c8-6(9)5-3-1-2-4-7-5/h1-4H,(H,8,9) checkY
    Key: SIOXPEMLGUPBBT-UHFFFAOYSA-N checkY
  • InChI=1/C6H5NO2/c8-6(9)5-3-1-2-4-7-5/h1-4H,(H,8,9)
    Key: SIOXPEMLGUPBBT-UHFFFAOYAC
  • c1ccnc(c1)C(=O)O
Properties
C6H5NO2
Molar mass 123.111 g·mol−1
Appearance White to tan crystalline solid
Melting point 136 to 138 °C (277 to 280 °F; 409 to 411 K)
Slightly soluble (0.41%) in water[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

Picolinic acid is an organic compound with the formula C
5H
4NCOOH). 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 that is soluble in water.

In synthetic organic chemistry, has been used as a substrate in the Mitsunobu reaction and in the Hammick reaction.[2]

Coordination chemistry

Picolinic acid is a bidentate chelating agent of elements such as chromium, zinc, manganese, copper, iron, and molybdenum in the human body.[3]: 72  Many of its complexes are charge-neutral and thus lipophilic. After its role in absorption was discovered, zinc picolinate dietary supplements became popular as they were shown to be an effective means of introducing zinc into the body.[3]

Production

Picolinic acid is formed from 2-methylpyridine by oxidation, e.g. by means of potassium permanganate (KMnO4).[4][5]

Biosynthesis

Picolinic acid is a catabolite of the amino acid tryptophan through the kynurenine pathway.[3][6] 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.[7]

Picolinates

Salts of picolinic acid (picolinates) include:

See also

References

  1. ^ Lide, DR. "CRC Handbook of Chemistry and Physics, Internet Version 2005, http://hbcpnetbase.com, CRC Press, Boca Raton, Florida, 2005". ((cite journal)): Cite journal requires |journal= (help)
  2. ^ Fuchs, Philip L. (29 July 2013). "Picolinic acid". Catalytic Oxidation Reagents. Wiley Inc. p. 495ff. ISBN 9781118704844. OCLC 954583821.
  3. ^ a b c Grant, RS; Coggan, SE; Smythe, GA (2009). "The physiological action of picolinic Acid in the human brain". International Journal of Tryptophan Research. 2: 71–9. doi:10.4137/ijtr.s2469. PMC 3195224. PMID 22084583.
  4. ^ Shimizu, Shinkichi; Watanabe, Nanao; Kataoka, Toshiaki; Shoji, Takayuki; Abe, Nobuyuki; Morishita, Sinji; Ichimura, Hisao (2007). "Pyridine and Pyridine Derivatives". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a22_399. ISBN 978-3527306732.
  5. ^ Harold Hart (Autor), Leslie E. Craine (Autor), David J. Hart (Autor), Christopher M. Hadad (Autor); Nicole Kindler (Übersetzer): Organische Chemie, 3. Auflage, Wiley-VCH, Weinheim 2007, ISBN 978-3-527-31801-8, S. 494.
  6. ^ Tan, L.; et al. (December 2012). "The kynurenine pathway in neurodegenerative diseases: mechanistic and therapeutic considerations". J Neurol Sci. 323 (1–2): 1–8. doi:10.1016/j.jns.2012.08.005. PMID 22939820. S2CID 6061945.
  7. ^ Evans, Gary (1982). "The Role of Picolinic Acid in Metal Metabolism". Life Chemistry Reports. 1. Harwood Academic Publishers: 57–67. Archived from the original on 26 January 2016. Retrieved 20 March 2015.

Categories