| 词条 | Picolinic acid |
| 释义 |
| Verifiedimages = changed | Watchedfields = changed | verifiedrevid = 464206292 | ImageFile1_Ref = {{chemboximage|correct|??}} | ImageFile1 =Picolinic acid.svg | ImageSize1 =180px | ImageFile2 =Picolinic-acid-3D-balls.png | ImageSize2 =180px | PIN = Pyridine-2-carboxylic acid | OtherNames = Picolinic acid |Section1={{Chembox Identifiers | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 993 | InChI = 1/C6H5NO2/c8-6(9)5-3-1-2-4-7-5/h1-4H,(H,8,9) | InChIKey = SIOXPEMLGUPBBT-UHFFFAOYAC | ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEMBL = 72628 | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 1S/C6H5NO2/c8-6(9)5-3-1-2-4-7-5/h1-4H,(H,8,9) | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = SIOXPEMLGUPBBT-UHFFFAOYSA-N | CASNo_Ref = {{cascite|correct|CAS}} | CASNo =98-98-6 | PubChem =1018 | ChEBI_Ref = {{ebicite|correct|EBI}} | ChEBI = 28747 | SMILES = c1ccnc(c1)C(=O)O }} |Section2={{Chembox Properties | C=6 | H=5 | N=1 | O=2 | Appearance =White to tan crystalline solid | Density = | MeltingPtC = 136 to 138 | MeltingPt_notes = | BoilingPt = | Solubility =Slightly Soluble (0.41%) in water [1] |Section3={{Chembox Hazards | MainHazards = | FlashPt = | AutoignitionPt = }} 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]{{rp|495ff}} Coordination chemistryPicolinic acid is a bidentate chelating agent of elements such as chromium, zinc, manganese, copper, iron, and molybdenum in the human body.[3]{{rp|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.[3] ProductionPicolinic acid is formed from 2-methylpyridine by oxidation, e.g. by means of potassium permanganate (KMnO4).[4][5] BiosynthesisPicolinic acid is a catabolite of the amino acid tryptophan through the kynurenine pathway.[3][6] Its function is unclear, but it has been implicated in a variety neuroprotective, immunological, and anti-proliferative affects. In addition, it is suggested to assist in the absorption of zinc(II) ions and other divalent or trivalent ions through the small intestine.[7] PicolinatesSalts of picolinic acid (picolinates) include,
See also
References1. ^{{cite journal|last=Lide|first=DR|title=CRC Handbook of Chemistry and Physics, Internet Version 2005, http://hbcpnetbase.com, CRC Press, Boca Raton, Florida, 2005. }} {{Glycinergics}}{{Use dmy dates|date=March 2018}}2. ^[https://books.google.com/books?id=Oa82AAAAQBAJ&q=picolinic+acid#v=snippet&q=picolinic%20acid&f=false Picolinic Acid] chapter in Philip L. Fuchs. Handbook of Reagents for Organic Synthesis: Catalytic Oxidation Reagents. John Wiley & Sons, Jul 29, 2013 {{ISBN|9781118704820}} 3. ^1 2 {{cite journal|last=Grant|first=RS|author2=Coggan, SE |author3=Smythe, GA |title=The physiological action of picolinic Acid in the human brain.|journal=International journal of tryptophan research : IJTR|year=2009|volume=2|pages=71–9|pmid=22084583|pmc=3195224}} 4. ^Shinkichi Shimizu, Nanao Watanabe, Toshiaki Kataoka, Takayuki Shoji, Nobuyuki Abe, Sinji Morishita, Hisao Ichimura: „Pyridine and Pyridine Derivatives“, in: Ullmann's Encyclopedia of Industrial Chemistry, 2002; {{DOI|10.1002/14356007.a22_399}}. 5. ^Harold Hart (Autor), Leslie E. Craine (Autor), David J. Hart (Autor), Christopher M. Hadad (Autor); Nicole Kindler (Übersetzer): Organische Chemie, 3. Auflage, Wiley-VCH, Weinheim 2007, {{ISBN|978-3-527-31801-8}}, S. 494. 6. ^{{cite journal | last1 = Tan | first1 = L | display-authors = etal | date = December 2012 | title = The kynurenine pathway in neurodegenerative diseases: mechanistic and therapeutic considerations | url = | journal = J Neurol Sci | volume = 323 | issue = 1-2| pages = 1–8 | doi = 10.1016/j.jns.2012.08.005 | pmid = 22939820 }} 7. ^{{cite journal |last=Evans |first=Gary |year=1982 |title=The Role of Picolinic Acid in Metal Metabolism |url=http://naldc.nal.usda.gov/download/46436/PDF |journal=Life Chemistry Reports |publisher=Harwood Academic Publishers |volume=1 |issue= |pages=57–67 |doi= |access-date=20 March 2015}} 4 : Pyridines|Glycine receptor agonists|Chelating agents|Aromatic acids |
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