Picolinic acid

Picolinic acid

Names
Preferred IUPAC name Pyridine-2-carboxylic acid
Other names Picolinic acid
Identifiers
CAS Number	98-98-6 Y
3D model (Jmol)	Interactive image
ChEBI	CHEBI:28747 Y
ChEMBL	ChEMBL72628 Y
ChemSpider	993 Y
ECHA InfoCard	100.002.472
PubChem	1018
InChI InChI=1S/C6H5NO2/c8-6(9)5-3-1-2-4-7-5/h1-4H,(H,8,9) Y Key: SIOXPEMLGUPBBT-UHFFFAOYSA-N Y InChI=1/C6H5NO2/c8-6(9)5-3-1-2-4-7-5/h1-4H,(H,8,9) Key: SIOXPEMLGUPBBT-UHFFFAOYAC
SMILES c1ccnc(c1)C(=O)O
Properties
Chemical formula	C6H5NO2
Molar mass	123.11 g·mol−1
Appearance	White to tan crystalline solid
Melting point	136 to 138 °C (277 to 280 °F; 409 to 411 K)
Solubility in water	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).
Y  (what is YN ?)
Infobox references

Picolinic acid is an organic compound with the formula C₅H₄N(CO₂H). It is a derivative of pyridine with a carboxylic acid substituent at the 2-position. It is an isomer of nicotinic acid, which has the carboxyl side chain at the 3-position. It is a white solid that is soluble in water.

In synthetic organic chemistry, has been used as a substrate in the Mitsunobu reaction and in the Hammick reaction.

Picolinic acid is a bidentate chelating agent of elements such as chromium, zinc, manganese, copper, iron, and molybdenum in the human body. 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 formed from 2-methylpyridine by oxidation, e.g. by means of potassium permanganate (KMnO₄).

Picolinic acid is a catabolite of the amino acid tryptophan through the kynurenine pathway.

It is a precursor to the coenzyme NAD⁺. In addition, it is suggested to assist in the absorption of zinc(II) ions and other divalent or trivalent ions through the small intestine.