Picolinic acid

Picolinic acid
IUPAC name

pyridine-2-carboxylic acid
Identifiers
CAS number 98-98-6 Y
PubChem 1018
ChemSpider 993 Y
ChEBI CHEBI:28747 Y
ChEMBL CHEMBL72628 Y
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
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
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.

Contents

Chelating properties

Picolinic acid acts as a chelating agent of elements such as chromium, zinc, manganese, copper, iron, and molybdenum in the human body. It is involved in phenylalanine, tryptophan, and alkaloid production, and for the quantitative detection of calcium.

The acid is believed to form a complex with zinc that may facilitate the passage of zinc through the gastrointestinal wall and into the circulatory system. A study of rats found that dietary picolinic acid increases the turnover and excretion of zinc.[1] Other results suggest that picolinic acid is a chelator which interacts with metals aside from zinc.[2] Commercially available picolinic acid is used as an intermediate to produce pharmaceuticals (especially local anesthetics) and metal salts for the application of nutritional supplements.

Pro-inflammatory properties

Picolinic acid induces macrophage inflammatory proteins,[3] an effect that is opposed by interferon-gamma (IFN-γ).[4]

See also

References

  1. ^ Evans GW, Johnson EC (January 1981). "Effect of iron, vitamin B-6 and picolinic acid on zinc absorption in the rat". J. Nutr. 111 (1): 68–75. PMID 7452375. http://jn.nutrition.org/cgi/pmidlookup?view=long&pmid=7452375. 
  2. ^ Aggett PJ, Fenwick PK, Kirk H (October 1989). "An in vitro study of the effect of picolinic acid on metal translocation across lipid bilayers". J. Nutr. 119 (10): 1432–7. PMID 2585133. http://jn.nutrition.org/cgi/pmidlookup?view=long&pmid=2585133. 
  3. ^ Maria Carla Bosco, Annamaria Rapisarda, Stefano Massazza, Giovanni Melillo, Howard Young and Luigi Varesio (2000). "The Tryptophan Catabolite Picolinic Acid Selectively Induces the Chemokines Macrophage Inflammatory Protein-1{alpha} and -1ß in Macrophages" (HTML). THE JOURNAL OF IMMUNOLOGY 164 (6): 3283–3291. PMID 10706721. http://www.jimmunol.org/cgi/content/full/164/6/3283. 
  4. ^ Bosco MC, Rapisarda A, Reffo G, Massazza S, Pastorino S, Varesio L (2003). "Macrophage activating properties of the tryptophan catabolite picolinic acid" (HTML). Advances in Experimental Medicine and Biology 527: 55–65. PMID 15206716.