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 |
|---|---|---|
| Blood glucose lowering and toxicological effects of zinc (II) complexes with maltol, threonine, and picolinic acid. | 2002 |
|
| Antagonistic effect of picolinic acid and interferon-gamma on macrophage inflammatory protein-1alpha/beta production. | 2002 Nov |
|
| ECNI GC-MS analysis of picolinic and quinolinic acids and their amides in human plasma, CSF, and brain tissue. | 2003 |
|
| Macrophage activating properties of the tryptophan catabolite picolinic acid. | 2003 |
|
| [Chromium as an essential element]. | 2003 |
|
| 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 |
|
| Formation, preservation, and cleavage of the disulfide bond by vanadium. | 2003 Apr 14 |
|
| Chromium compounds: cytotoxicity and carcinogenesis. | 2003 Apr 15 |
|
| Membrane differential filtration is safe and effective for the long-term treatment of Refsum syndrome--an update of treatment modalities and pathophysiological cognition. | 2003 Aug |
|
| Cellular antiendotoxin activities of lung surfactant protein C in lipid vesicles. | 2003 Aug 1 |
|
| Kinetics and mechanistic studies of anticarcinogenic bisperoxovanadium(V) compounds: ligand substitution reactions at physiological pH and relevance to DNA interactions. | 2003 Dec 1 |
|
| Dipicolinic acid prevents the copper-dependent oxidation of low density lipoprotein. | 2003 Feb |
|
| 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 |
|
| Study of the mechanism of the cytostatic effect of picolinic acid on proliferating Tetrahymena pyriformis cells. | 2003 Jul-Aug |
|
| Effect of chromium picolinate on histopathological alterations in STZ and neonatal STZ diabetic rats. | 2003 Jul-Sep |
|
| Discovery and structural modification of inhibitors of methionine aminopeptidases from Escherichia coli and Saccharomyces cerevisiae. | 2003 Jun 19 |
|
| Ruthenium(III) triazacyclononane dithiocarbamate, pyridinecarboxylate, or aminocarboxylate complexes as scavengers of nitric oxide. | 2003 Jun 30 |
|
| Antioxidant properties of chromium and zinc: in vivo effects on digestibility, lipid peroxidation, antioxidant vitamins, and some minerals under a low ambient temperature. | 2003 May |
|
| Antifungal activity of macrophages engineered to produce IFNgamma: inducibility by picolinic acid. | 2003 May |
|
| Harnessing chromium in the fight against diabetes. | 2003 Nov 1 |
|
| 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 |
|
| Turning off phototriggered linkage isomerizations in ruthenium dimethyl sulfoxide complexes. | 2003 Nov 17 |
|
| Diuretics vs. ACE inhibitors. | 2003 Oct |
|
| A new family of insulin-mimetic vanadium complexes derived from 5-carboalkoxypicolinates. | 2003 Oct 17 |
|
| [Chromium (III)-ion enhances the utilization of glucose in type-2 diabetes mellitus]. | 2003 Oct 19 |
|
| Synthesis of alpha-amino acids via asymmetric phase transfer-catalyzed alkylation of achiral nickel(II) complexes of glycine-derived Schiff bases. | 2003 Oct 22 |
|
| 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 |
|
| Effects of treatment with chromium picolinate on peripheral amino acid availability and brain monoamine function in the rat. | 2003 Sep |
|
| 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 |
|
| Synthesis and characterization of a new family of bi-, tri-, tetra-, and pentanuclear ferric complexes. | 2004 Aug 9 |
|
| Recent advances in the nutritional biochemistry of trivalent chromium. | 2004 Feb |
|
| Alpha-picolinic acid, a fungal toxin and mammal apoptosis-inducing agent, elicits hypersensitive-like response and enhances disease resistance in rice. | 2004 Feb |
|
| Hypoxia selectively inhibits monocyte chemoattractant protein-1 production by macrophages. | 2004 Feb 1 |
|
| Dietary L-carnitine increases plasma leptin concentrations of gestating sows fed one meal per day. | 2004 Jan |
|
| Type I methionine aminopeptidase from Saccharomyces cerevisiae is a potential target for antifungal drug screening. | 2004 Jul |
|
| Nikkomycin biosynthesis: formation of a 4-electron oxidation product during turnover of NikD with its physiological substrate. | 2004 Jul 20 |
|
| A new electrochemical system for stereoselective allylic hydroxylation of cholesteryl acetate with dioxygen induced by iron picolinate complexes. | 2004 Jun |
|
| Determining the safety of chromium tripicolinate for addition to foods as a nutrient supplement. | 2004 Jun |
|
| Picolinic acid- or desferrioxamine-inducible autocrine activation of macrophages engineered to produce IFNgamma: an approach for gene therapy. | 2004 Mar |
|
| Induction of Mycobacterium avium growth restriction and inhibition of phagosome-endosome interactions during macrophage activation and apoptosis induction by picolinic acid plus IFNgamma. | 2004 May |
|
| Absorption of the biomimetic chromium cation triaqua-mu3-oxo-mu-hexapropionatotrichromium(III) in rats. | 2004 May |
|
| Direct determination of copper in urine using a sol-gel optical sensor coupled to a multicommutated flow system. | 2004 Sep |
|
| 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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| Record Status |
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m8785
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SUB35118
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PICOLINIC ACID
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