Picolinic acid is an organic compound with the formula C5H4N(CO2H). 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-position, respectively. It is a white solid that is soluble in water.
|Preferred IUPAC name
3D model (JSmol)
CompTox Dashboard (EPA)
|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|
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
|what is ?)(|
Picolinic acid is a bidentate chelating agent of elements such as chromium, zinc, manganese, copper, iron, and molybdenum in the human body.:72 Many of its complexes are charge-neutral and thus lipophilic. After its role in absorption was discovered, zinc dipicolinate dietary supplements became popular as they were shown to be an effective means of introducing zinc into the body.
Picolinic acid is a catabolite of the amino acid tryptophan through the kynurenine pathway. Its function is unclear, but it has been implicated in a variety 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.
Salts of picolinic acid (picolinates) include:
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- 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.
- 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.
- 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.
- Evans, Gary (1982). "The Role of Picolinic Acid in Metal Metabolism". Life Chemistry Reports. Harwood Academic Publishers. 1: 57–67. Retrieved 20 March 2015.