Picolinic acid

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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

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

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

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. OCLC 954583821
    .
  3. ^
    PMID 22084583
    .
  4. ISBN 978-3527306732
    .
  5. ISBN 978-3-527-31801-8
    , S. 494.
  6. 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.

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