Movatterモバイル変換

[0]ホーム
URL:

Jump to content
WikipediaThe Free Encyclopedia
Search

Picolinic acid

From Wikipedia, the free encyclopedia
Pyridine-2-carboxylic acid; bidentate chelating agent
Picolinic acid
Names
Preferred IUPAC name
Pyridine-2-carboxylic acid
Other names
Picolinic acid
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard100.002.472Edit this at Wikidata
UNII
  • InChI=1S/C6H5NO2/c8-6(9)5-3-1-2-4-7-5/h1-4H,(H,8,9) checkY
    Key: SIOXPEMLGUPBBT-UHFFFAOYSA-N checkY
  • InChI=1/C6H5NO2/c8-6(9)5-3-1-2-4-7-5/h1-4H,(H,8,9)
    Key: SIOXPEMLGUPBBT-UHFFFAOYAC
  • c1ccnc(c1)C(=O)O
Properties
C6H5NO2
Molar mass123.111 g·mol−1
AppearanceWhite solid
Density1.526 g/cm³
Melting point136 to 138 °C (277 to 280 °F; 409 to 411 K)
Slightly soluble (0.41%) in water[1]
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)
Chemical compound

Picolinic acid is anorganic compound with the formulaNC5H4CO2H. It is a derivative ofpyridine with acarboxylic acid (COOH) substituent at the 2-position. It is anisomer ofnicotinic acid andisonicotinic acid, which have the carboxyl side chain at the 3- and 4-positions, respectively. It is a white solid although impure samples can appear tan. The compound is soluble in water.

Production

[edit]

On a commercial scale, picolinic acid is produced byammoxidation of 2-picoline followed byhydrolysis of the resultingnitrile:

NC5H4CH3 + 1.5 O2 + NH3 → NC5H4C≡N + 3 H2O
NC5H4C≡N + 2 H2O → NC5H4CO2H + NH3

It is also produced by oxidation of picoline withnitric acid.[2]

In the laboratory, picolinic acid is formed from2-methylpyridine byoxidation withpotassium permanganate (KMnO4).[3][4]

Reactions

[edit]
Structure of Zn(picolinate)2(H2O)2.

Hydrogenation of picolinic acid gives piperidine-2-carboxylic acid, a precursor to the drugMepivacaine.

Picolinic acid is a bidentatechelating agent of elements such as chromium, zinc, manganese, copper, iron, and molybdenum in the human body.[5][6]

It is a substrate in theMitsunobu reaction. In theHammick reaction, picolinic acid reacts with ketones to give pyridine-2-carbonols:[7]

NC5H4CO2H + R2C=O → NC5H4CR2(OH) + CO2

Biosynthesis

[edit]

Picolinic acid is acatabolite of the amino acidtryptophan through thekynurenine pathway.[8] Its function is unclear, but it has been implicated in a variety of neuroprotective, immunological, and anti-proliferative effects. In addition, it is suggested to assist in the absorption of zinc(II) ions and otherdivalent or trivalent ions through thesmall intestine.[9]

Picolinates

[edit]

Salts of picolinic acid (picolinates) include:

See also

[edit]

References

[edit]
  1. ^Lide, DR. "CRC Handbook of Chemistry and Physics, Internet Version 2005,http://hbcpnetbase.com, CRC Press, Boca Raton, Florida, 2005".{{cite journal}}:Cite journal requires|journal= (help);External link in|title= (help)
  2. ^Shimizu, Shinkichi; Watanabe, Nanao; Kataoka, Toshiaki; Shoji, Takayuki; Abe, Nobuyuki; Morishita, Sinji; Ichimura, Hisao (2007). "Pyridine and Pyridine Derivatives".Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH.doi:10.1002/14356007.a22_399.ISBN 978-3-527-30673-2.
  3. ^Singer, Alvin W.; McElvain, S. M. (1940). "Picolinic Acid Hydrochloride".Organic Syntheses.20: 79.doi:10.15227/orgsyn.020.0079.
  4. ^Harold Hart, Leslie E. Craine, David J. Hart, Christopher M. Hadad; Nicole Kindler (2007).'Organische Chemie 3. Auflage. Weinheim: Wiley-VCH. p. 494.ISBN 978-3-527-31801-8.{{cite book}}: CS1 maint: multiple names: authors list (link)
  5. ^Lumme, Paavo; Lundgren, Georg; Mark, Wanda; Lundström, Hans; Borch, Gunner; Craig, J. Cymerman (1969). "The Crystal Structure of Zinc Picolinate Tetrahydrate, Zn(C6H4O2N)2(H2O)4".Acta Chemica Scandinavica.23:3011–3022.doi:10.3891/acta.chem.scand.23-3011.
  6. ^Daugulis, Olafs; Roane, James; Tran, Ly Dieu (2015)."Bidentate, Monoanionic Auxiliary-Directed Functionalization of Carbon–Hydrogen Bonds".Accounts of Chemical Research.48 (4):1053–1064.doi:10.1021/ar5004626.PMC 4406856.PMID 25756616.
  7. ^Fuchs, Philip L. (29 July 2013)."Picolinic acid".Catalytic Oxidation Reagents. Wiley Inc. p. 495ff.ISBN 9781118704844.OCLC 954583821.
  8. ^Tan, L.; et al. (December 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.S2CID 6061945.
  9. ^Evans, Gary (1982)."The Role of Picolinic Acid in Metal Metabolism".Life Chemistry Reports.1. Harwood Academic Publishers:57–67. Archived fromthe original on 26 January 2016. Retrieved20 March 2015.
Receptor
(ligands)
GlyRTooltip Glycine receptor
NMDARTooltip N-Methyl-D-aspartate receptor
Transporter
(blockers)
GlyT1Tooltip Glycine transporter 1
GlyT2Tooltip Glycine transporter 2

Retrieved from "https://en.wikipedia.org/w/index.php?title=Picolinic_acid&oldid=1265974551"
Categories:
Hidden categories:
[8]ページ先頭
©2009-2026 Movatter.jp