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Pyridine-2-carboxylic acid; bidentate chelating agent From Wikipedia, the free encyclopedia
Picolinic acid is an organic compound with the formula NC5H4CO2H. 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-positions, respectively. It is a white solid although impure samples can appear tan. The compoundthat is soluble in water.
Names | |
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Preferred IUPAC name
Pyridine-2-carboxylic acid | |
Other names
Picolinic acid | |
Identifiers | |
3D model (JSmol) |
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ChEBI | |
ChEMBL | |
ChemSpider | |
ECHA InfoCard | 100.002.472 |
PubChem CID |
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UNII | |
CompTox Dashboard (EPA) |
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Properties | |
C6H5NO2 | |
Molar mass | 123.111 g·mol−1 |
Appearance | White solid |
Density | 1.526 g/cm³ |
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).
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On a commercial scale, picolinic acid is produced by ammoxidation of 2-picoline followed by hydrolysis of the resulting nitrile:
It is also produced by oxidation of picoline with nitric acid.[2]
In the laboratory, picolinic acid is formed from 2-methylpyridine by oxidation with potassium permanganate (KMnO4).[3][4]
Hydrogenation of picolinic acid gives piperidine-2-carboxylic acid, a precursor to the drug Mepivacaine.
Picolinic acid is a bidentate chelating agent of elements such as chromium, zinc, manganese, copper, iron, and molybdenum in the human body.[5][6]
It is a substrate in the Mitsunobu reaction. In the Hammick reaction, picolinic acid reacts with ketones to give pyridine-2-carbonols:[7]
Picolinic acid is a catabolite of the amino acid tryptophan through the kynurenine pathway.[8] 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.[9]
Salts of picolinic acid (picolinates) include:
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