Picolinic acid

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Picolinic acid
Picolinic acid.svg
Picolinic-acid-3D-balls.png
Identifiers
CAS number 98-98-6 YesY
PubChem 1018
ChemSpider 993 YesY
ChEBI CHEBI:28747 YesY
ChEMBL CHEMBL72628 YesY
Jmol-3D images Image 1
Properties
Molecular formula C6H5NO2
Molar mass 123.11 g mol−1
Appearance White to tan crystalline solid
Melting point 136-138 °C
Solubility in water 887 g/L[1]
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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Infobox references

Picolinic acid is a pyridine compound with a carboxyl side chain at the 2-position. It is an isomer of nicotinic acid, which has the carboxyl side chain at the 3-position. It is a catabolite of the amino acid tryptophan through the kynurenine pathway.[1][2]

Picolinic acid acts as a chelating agent of elements such as chromium, zinc, manganese, copper, iron, and molybdenum in the human body.[1]:72

In synthetic organic chemistry, has been used as a substrate in the Mitsunobu reaction and in the Hammick reaction.[3]:495ff

See also[edit]

References[edit]

  1. ^ 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 : IJTR 2: 71–9. PMC 3195224. PMID 22084583. Retrieved 22 January 2013. 
  2. ^ Tan L et al. The kynurenine pathway in neurodegenerative diseases: mechanistic and therapeutic considerations. J Neurol Sci. 2012 Dec 15;323(1-2):1-8. PMID 22939820
  3. ^ Picolinic Acid chapter in Philip L. Fuchs. Handbook of Reagents for Organic Synthesis: Catalytic Oxidation Reagents. John Wiley & Sons, Jul 29, 2013 ISBN 9781118704820