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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2014/01/13 18:06:21」(JST)

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Picolinic acid is a pyridine compound with a carboxyl side chain at the 2-position. It is an isomer of nicotinic acid, which has the carboxyl side chain at the 3-position. It is a catabolite of the amino acid tryptophan.

Chelating properties[edit]

Picolinic acid acts as a chelating agent of elements such as chromium, zinc, manganese, copper, iron, and molybdenum in the human body. It is involved in phenylalanine, tryptophan, and alkaloid production,^{[citation needed]} and for the quantitative detection of calcium.

The acid is believed to form a complex with zinc that may facilitate the passage of zinc through the gastrointestinal wall and into the circulatory system. A study of rats found that dietary picolinic acid increases the turnover and excretion of zinc.^[2] Other results suggest that picolinic acid is a chelator which interacts with metals aside from zinc.^[3] Commercially available picolinic acid is used as an intermediate to produce pharmaceuticals (especially local anesthetics) and metal salts for the application of nutritional supplements.

References[edit]

^ Grant, RS; Coggan, SE; Smythe, GA (2009). "The physiological action of picolinic Acid in the human brain.". International journal of tryptophan research : IJTR 2: 71–9. PMC 3195224. PMID 22084583. Retrieved 22 January 2013. Cite uses deprecated parameters (help)
^ Evans GW, Johnson EC (January 1981). "Effect of iron, vitamin B-6 and picolinic acid on zinc absorption in the rat". J. Nutr. 111 (1): 68–75. PMID 7452375. Cite uses deprecated parameters (help)
^ Aggett PJ, Fenwick PK, Kirk H (October 1989). "An in vitro study of the effect of picolinic acid on metal translocation across lipid bilayers". J. Nutr. 119 (10): 1432–7. PMID 2585133. Cite uses deprecated parameters (help)

UpToDate Contents

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1. 成人における肥満：薬物療法 obesity in adults drug therapy
2. 成人における糖尿病に対する治療の概要 overview of medical care in adults with diabetes mellitus

English Journal

Comparison of tissue metal concentrations in zucker lean, zucker obese, and zucker diabetic Fatty rats and the effects of chromium supplementation on tissue metal concentrations.

Staniek H, Rhodes NR, Di Bona KR, Deng G, Love ST, Pledger LA, Blount J, Gomberg E, Grappe F, Cernosek C, Peoples B, Rasco JF, Krejpcio Z, Vincent JB.SourceDepartment of Human Nutrition and Hygiene, Poznan University of Life Sciences, Wojska Polskiego 31, 60-624, Poznan, Poland.
Biological trace element research.Biol Trace Elem Res.2013 Mar;151(3):373-83. doi: 10.1007/s12011-012-9565-8. Epub 2012 Dec 19.
Diabetes results in several metabolic changes, including alterations in the transport, distribution, excretion, and accumulation of metals. While changes have been examined in several rat models of insulin resistance and diabetes, the metal ion concentrations in the tissues of Zucker lean, Zucker ob
PMID 23250541

Anti-atherogenic effect of chromium picolinate in streptozotocin-induced experimental diabetes ().

Sundaram B, Singhal K, Sandhir R.SourceDepartment of Biochemistry, Panjab University, Chandigarh, India.
Journal of diabetes.J Diabetes.2013 Mar;5(1):43-50. doi: 10.1111/j.1753-0407.2012.00211.x.
Background: Several studies have implicated changes in the levels of trace elements in diabetes. Chromium is one such element that seems to potentiate insulin action, thereby regulating carbohydrate and lipid metabolism. The aim of the present study was to evaluate the effect of chromium suppleme
PMID 22650796

Selection of Chiral Zinc Catalysts for the Kinetic Resolution of Esters via Dynamic Templating.

Kannappan R, Nicholas KM.SourceDepartment of Chemistry and Biochemistry, Stephenson Life Sciences Research Center, University of Oklahoma , Norman, Oklahoma 73019, United States.
ACS combinatorial science.ACS Comb Sci.2013 Feb 11;15(2):90-100. doi: 10.1021/co3001023. Epub 2013 Jan 22.
Dynamic combinatorial libraries of chiral tetradentate bis-imine zinc(II) complexes have been prepared and screened for (1) their discrimination of enantiomeric picolinate esters and pyridyl phosphonate transition state analogs (TSAs) and (2) their catalytic activity and selectivity for enantioselec
PMID 23240865

Japanese Journal

Single-Layer Blue Electrophosphorescent Organic Light-Emitting Diodes Based on Small-Molecule Mixed Hosts: Comparison between the Solution and Vacuum Fabrication Processes

Liu Shun-Wei,Chang Yung-Ting,Lee Chih-Chien,Yuan Chih-Hsien,Liu Li-An,Chen Yu-San,Lin Chun-Feng,Wu Chih-I,Chen Chin-Ti
Jpn J Appl Phys 52(1), 012101-012101-6, 2013-01-25
… All active components including SimCP2, 1,3-bis[(4-tert-butylphenyl)-1,3,4-oxadiazolyl]phenylene (OXD-7), and iridium(III) bis[(4,6-di-fluorophenyl)-pyridinato-N,C^{2}] picolinate (FIrpic) were mixed in an organic solution for wet processing in the fabrication of single-layer PHOLEDs. …
NAID 150000106276

Two-way Linkage Photoisomerization of [Ru(2,2':6',2"-terpyridine)(6-{(methylsulfinyl)methyl}picolinate)]BF_4

, ,
Chemistry letters 42(1), 17-18, 2013-01-05
… [Ru(tpy)(picSO)]BF4 (tpy: 2,2′:6′,2′′-terpyridine, picSO: 6-[(methylsulfinyl)methyl]picolinate) undergoes profound linkage isomerization behavior between stable S-bound and metastable O-bound isomers. …
NAID 10031143784

銅化合物による心血管障害及び糖尿病治療への実験的試み

桜井弘
薬学雑誌. 乙号 132(3), 285-291, 2012
… (1) improvement of cardiovascular dysfunction in animals by di-nuclear Cu-asprinate complex on the basis of the results on its reactive oxygen scavenging (ROS) effect, (2) blood glucose-lowering effect of mono-nuclear Cu-picolinate complex in streptozotocin (STZ)-induced type 1-like diabetic animals, based on the results on in vitro insulinomimetic activity, and (3) anti-diabetic effect of copper sulfate in animals with regard to the inhibition of α-glucosidase activity. …
NAID 130001872022

Related Pictures

★リンクテーブル★

リンク元	「ピコリン酸」「picolinic acid」
拡張検索	「dihydrodipicolinate reductase」「chromium picolinate」

「ピコリン酸」

Picolinic acid
	IUPAC name pyridine-2-carboxylic acid
Identifiers
CAS number	98-98-6
PubChem	1018
ChemSpider	993
ChEBI	CHEBI:28747
ChEMBL	CHEMBL72628
Jmol-3D images	Image 1
	SMILES c1ccnc(c1)C(=O)O ;
	InChI InChI=1S/C6H5NO2/c8-6(9)5-3-1-2-4-7-5/h1-4H,(H,8,9) ; Key: SIOXPEMLGUPBBT-UHFFFAOYSA-N InChI=1/C6H5NO2/c8-6(9)5-3-1-2-4-7-5/h1-4H,(H,8,9); Key: SIOXPEMLGUPBBT-UHFFFAOYAC ;
Properties
Molecular formula	C6H5NO2
Molar mass	123.11 g mol−1
Appearance	White to tan crystalline solid
Melting point	136-138 °C
Solubility in water	887 g/L
	(verify) (what is: /?); Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
	Infobox references