Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C6H5NO2 |
| Molecular Weight | 123.1094 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
OC(=O)C1=NC=CC=C1
InChI
InChIKey=SIOXPEMLGUPBBT-UHFFFAOYSA-N
InChI=1S/C6H5NO2/c8-6(9)5-3-1-2-4-7-5/h1-4H,(H,8,9)
| Molecular Formula | C6H5NO2 |
| Molecular Weight | 123.1094 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
DescriptionCurator's Comment: description was created based on several sources, including
https://en.wikipedia.org/wiki/Picolinic_acid
Curator's Comment: description was created based on several sources, including
https://en.wikipedia.org/wiki/Picolinic_acid
Picolinic acid is an organic compound, is a derivative of pyridine with a carboxylic acid substituent at the 2-position. 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 an endogenous metabolite of L-tryptophan (TRP) that has been reported to possess a wide range of neuroprotective, immunological, and anti-proliferative effects within the body. However, the salient physiological function of this molecule is yet to be established. The synthesis of picolinic acid as a product of the kynurenine pathway (KP) suggests that, similar to other KP metabolites, picolinic acid may play a role in the pathogenesis of inflammatory disorders within the CNS and possibly other organs.
Approval Year
Doses
| Dose | Population | Adverse events |
|---|---|---|
10 % 2 times / day multiple, topical (unknown) Studied dose Dose: 10 %, 2 times / day Route: topical Route: multiple Dose: 10 %, 2 times / day Sources: |
unhealthy n = 20 Health Status: unhealthy Condition: acne vulgaris Sex: M+F Food Status: UNKNOWN Population Size: 20 Sources: |
Disc. AE: Burning skin... AEs leading to discontinuation/dose reduction: Burning skin (1 pt) Sources: |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| Burning skin | 1 pt Disc. AE |
10 % 2 times / day multiple, topical (unknown) Studied dose Dose: 10 %, 2 times / day Route: topical Route: multiple Dose: 10 %, 2 times / day Sources: |
unhealthy n = 20 Health Status: unhealthy Condition: acne vulgaris Sex: M+F Food Status: UNKNOWN Population Size: 20 Sources: |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Separation and direct UV detection of lanthanides complexed with pyridine-2-carboxylic acid by capillary electrophoresis. | 2001 Jul 27 |
|
| Oral chromium picolinate and control of glycemia in insulin-treated diabetic dogs. | 2001 Jul-Aug |
|
| Antiviral, cytotoxic and apoptotic activities of picolinic acid on human immunodeficiency virus-1 and human herpes simplex virus-2 infected cells. | 2001 Nov-Dec |
|
| Auxin herbicides induce H(2)O(2) overproduction and tissue damage in cleavers (Galium aparine L.). | 2001 Sep |
|
| Blood glucose lowering and toxicological effects of zinc (II) complexes with maltol, threonine, and picolinic acid. | 2002 |
|
| Assessment of chromium tripicolinate supplementation and dietary energy level and source on growth, carcass, and blood criteria in growing pigs. | 2002 Feb |
|
| Effect of chromium tripicolinate supplementation on porcine immune response during the periparturient and neonatal period. | 2002 Feb |
|
| In vivo distribution of chromium from chromium picolinate in rats and implications for the safety of the dietary supplement. | 2002 Feb |
|
| Development of new insulinomimetic zinc(II) picolinate complexes with a Zn(N2O2) coordination mode: structure characterization, in vitro, and in vivo studies. | 2002 Jan |
|
| Cytotoxicity and oxidative mechanisms of different forms of chromium. | 2002 Oct 30 |
|
| Assessment of chromium tripicolinate supplementation and dietary protein level on growth, carcass, and blood criteria in growing pigs. | 2002 Sep |
|
| The potential value and toxicity of chromium picolinate as a nutritional supplement, weight loss agent and muscle development agent. | 2003 |
|
| Chromium picolinate for reducing body weight: meta-analysis of randomized trials. | 2003 Apr |
|
| Chromium compounds: cytotoxicity and carcinogenesis. | 2003 Apr 15 |
|
| Tissue and subcellular distribution of chromium picolinate with time after entering the bloodstream. | 2003 Feb 1 |
|
| Synthesis of 6-formyl-pyridine-2-carboxylate derivatives and their telomerase inhibitory activities. | 2003 Feb 24 |
|
| Cationic sigma-phenylplatinum(II) complexes with carboxylic acid functionality: pK(a) determinations and x-ray structures. | 2003 Feb 24 |
|
| The preparation of (S)-aspartate semi-aldehyde appropriate for use in biochemical studies. | 2003 Jan 20 |
|
| Study of the mechanism of the cytostatic effect of picolinic acid on proliferating Tetrahymena pyriformis cells. | 2003 Jul-Aug |
|
| Reactivity of 2-pyridinecarboxylic esters with cadmium(II) halides: study of (113)Cd NMR solid state spectra and crystal structures of hexacoordinated complexes [CdI(2)(C(5)H(4)NCOOMe)(2)] and [CdI(2)(C(5)H(4)NCOOPr(n))(2)]. | 2003 Nov 17 |
|
| A new family of insulin-mimetic vanadium complexes derived from 5-carboalkoxypicolinates. | 2003 Oct 17 |
|
| Regulation of geometry around the ruthenium center of bis(2-pyridinecarboxylato) complexes by the nitrosyl moiety: syntheses, structures, and theoretical studies. | 2003 Oct 6 |
|
| Synthesis of a pyridinium bis[citrato(2-)]oxochromate(V) complex and its ligand-exchange reactions. | 2003 Oct 6 |
|
| Metabolites of the kynurenine pathway of tryptophan metabolism in the cerebrospinal fluid of Malawian children with malaria. | 2003 Sep 15 |
|
| Reactions of the dirhenium(II) complex Re2Cl4(mu-dppm)2 with pyridinecarboxylic acids. Examples of bidentate O,O versus N,O coordination and tridentate O,N,O coordination and structural isomers that contain the pyridine-2,6-dicarboxylate ligand. | 2003 Sep 22 |
|
| Conformational changes combined with charge-transfer interactions are essential for reduction in catalysis by p-hydroxybenzoate hydroxylase. | 2003 Sep 30 |
|
| Chromium picolinate supplementation improves insulin sensitivity in Goto-Kakizaki diabetic rats. | 2004 |
|
| Relation between electrophoretic behavior and molecular shapes of aromatic anions. | 2004 Apr |
|
| Determining the safety of chromium tripicolinate for addition to foods as a nutrient supplement. | 2004 Jun |
|
| Recent developments in the biochemistry of chromium(III). | 2004 Summer |
Patents
| Substance Class |
Chemical
Created
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| Record UNII |
QZV2W997JQ
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Validated (UNII)
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M8785
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PICOLINIC ACID
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ACTIVE MOIETY |
