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Picolinic acid

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Picolinic acid

Names
IUPAC name
pyridine-2-carboxylic acid
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.002.472 Edit this at Wikidata
  • 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 136-138 °C
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 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.

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,[citation needed] 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 (1981). "Effect of iron, vitamin B-6 and picolinic acid on zinc absorption in the rat". J. Nutr. 111 (1): 68–75. PMID 7452375. {{cite journal}}: Unknown parameter |month= ignored (help)
  2. ^ Aggett PJ, Fenwick PK, Kirk H (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. {{cite journal}}: Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)
  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-1α and -1β in Macrophages". Journal of Immunology. 164 (6): 3283–3291. PMID 10706721.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  4. ^ Bosco MC, Rapisarda A, Reffo G, Massazza S, Pastorino S, Varesio L (2003). "Macrophage activating properties of the tryptophan catabolite picolinic acid". Advances in Experimental Medicine and Biology. 527: 55–65. PMID 15206716.{{cite journal}}: CS1 maint: multiple names: authors list (link)
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