関: chromium picolinate、picolinate

WordNet

street name for lysergic acid diethylamide (同)back breaker, battery-acid, dose, dot, Elvis, loony toons, Lucy in the sky with diamonds, pane, superman, window pane, Zen
any of various water-soluble compounds having a sour taste and capable of turning litmus red and reacting with a base to form a salt
having the characteristics of an acid; "an acid reaction"

PrepTutorEJDIC

酸性の / 酸味のある,すっぱい(sour) / (言葉・態度などが)厳しい,しんらつな / 酸 / すっぱいもの / 《俗》=LSD

Wikipedia preview

出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2016/08/15 00:26:52」(JST)

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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.^[2]^:495ff

Coordination chemistry

Picolinic acid is a bidentate chelating agent of elements such as chromium, zinc, manganese, copper, iron, and molybdenum in the human body.^[3]^:72 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.^[4]

Biosynthesis

Picolinic acid is a catabolite of the amino acid tryptophan through the kynurenine pathway.^[3]^[5]

It is a precursor to the coenzyme NAD⁺.^[4] In addition, it is suggested to assist in the absorption of zinc(II) ions and other divalent or trivalent ions through the small intestine.^[6]

References

^ Lide, DR. "CRC Handbook of Chemistry and Physics, Internet Version 2005, http://hbcpnetbase.com, CRC Press, Boca Raton, FL, 2005.".
^ Picolinic Acid chapter in Philip L. Fuchs. Handbook of Reagents for Organic Synthesis: Catalytic Oxidation Reagents. John Wiley & Sons, Jul 29, 2013 ISBN 9781118704820
^ ^a ^b 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. |access-date= requires |url= (help)
^ ^a ^b Grant, R.; Coggan, S.; Smythe, G. (2009). "The Physiological Action of Picolinic Acid in the Human Brain". International Journal of Tryptophan Research. Libertas Academica. 2: 71–79. PMC 3195224. PMID 22084583.
^ Tan, L; et al. (Dec 2012). "The kynurenine pathway in neurodegenerative diseases: mechanistic and therapeutic considerations". J Neurol Sci. 323 (1-2): 1–8. doi:10.1016/j.jns.2012.08.005. PMID 22939820.
^ Evans, Gary (1982). "The Role of Picolinic Acid in Metal Metabolism". Life Chemistry Reports. Harwood Academic Publishers. 1: 57–67. Retrieved 20 March 2015.

UpToDate Contents

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English Journal

Changes in Tryptophan Catabolite (TRYCAT) Pathway Patterning Are Associated with Mild Impairments in Declarative Memory in Schizophrenia and Deficits in Semantic and Episodic Memory Coupled with Increased False-Memory Creation in Deficit Schizophrenia.

Kanchanatawan B1, Hemrungrojn S1, Thika S1, Sirivichayakul S2, Ruxrungtham K2, Carvalho AF3, Geffard M4,5, Anderson G6, Maes M7,8,9,10.
Molecular neurobiology.Mol Neurobiol.2018 Jun;55(6):5184-5201. doi: 10.1007/s12035-017-0751-8. Epub 2017 Sep 5.
PMID 28875464

Prospective metabolomics study identifies potential novel blood metabolites associated with pancreatic cancer risk.

Shu X1, Zheng W1, Yu D1, Lan Li H2, Lan Q3, Yang G1, Cai H1, Ma X2, Rothman N3, Gao YT2, Jia W4,5, Xiang YB2, Shu XO1.
International journal of cancer.Int J Cancer.2018 May 1. doi: 10.1002/ijc.31574. [Epub ahead of print]
PMID 29717485

Experiment and theory at the convergence limit: accurate equilibrium structure of picolinic acid by gas-phase electron diffraction and coupled-cluster computations.

Vogt N1, Marochkin II1, Rykov AN2.
Physical chemistry chemical physics : PCCP.Phys Chem Chem Phys.2018 Apr 18;20(15):9787-9795. doi: 10.1039/C8CP00310F.
PMID 29564453

Japanese Journal

Stereochemical Stability Differences between Axially Chiral 6-Aryl-Substituted Picolinic Esters and Their Benzoic Ester Derivatives : sp²N: vs. sp²CH in CH₃, C₆H₅, and CH₃O ortho-Substitution Effect

Bulletin of the Chemical Society of Japan 88(12), 1726-1734, 2015
NAID 130005113802

Synthesis of picolinate-iron(III) compounds through an aqueous solution process

Journal of the Ceramic Society of Japan 123(1441), 751-755, 2015
NAID 130005096349

Large Amounts of Picolinic Acid Are Lethal but Small Amounts Increase the Conversion of Tryptophan-Nicotinamide in Rats

Journal of Nutritional Science and Vitaminology 60(5), 334-339, 2014
NAID 130004773628

「ピコリン酸」

Picolinic acid
Names
	IUPAC name pyridine-2-carboxylic acid
Identifiers
CAS Number	98-98-6
ChEBI	CHEBI:28747
ChEMBL	ChEMBL72628
ChemSpider	993
Jmol 3D model	Interactive image
PubChem	1018
	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 ;
	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).
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	Infobox references