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
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard
100.002.472
UNII
InChI=1S/C6H5NO2/c8-6(9)5-3-1-2-4-7-5/h1-4H,(H,8,9)
Y Key: SIOXPEMLGUPBBT-UHFFFAOYSA-N
Y InChI=1/C6H5NO2/c8-6(9)5-3-1-2-4-7-5/h1-4H,(H,8,9)
Key: SIOXPEMLGUPBBT-UHFFFAOYAC
Properties
C 6 H 5 N O 2
Molar mass
123.111 g·mol−1
Appearance
White to tan crystalline solid
Melting point
136 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 their
standard state (at 25 °C [77 °F], 100 kPa).
Chemical compound
Picolinic acid is an
organic compound with the formula C5 H4 NCOOH ). It is a derivative of
pyridine with a
carboxylic acid (COOH) substituent at the 2-position. It is an
isomer of
nicotinic acid and
isonicotinic acid , which have the carboxyl side chain at the 3- and 4-positions, respectively. 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]
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 picolinate
dietary supplements became popular as they were shown to be an effective means of introducing
zinc into the body.
[3]
Production
Picolinic acid is formed from
2-methylpyridine by
oxidation , e.g. by means of
potassium permanganate (KMnO4 ).
[4]
[5]
Biosynthesis
Picolinic 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 of neuroprotective, immunological, and anti-proliferative effects. 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]
Picolinates
Salts of picolinic acid (picolinates) include:
See also
References
^ Lide, DR. "CRC Handbook of Chemistry and Physics, Internet Version 2005,
http://hbcpnetbase.com , CRC Press, Boca Raton, Florida, 2005".
^ Fuchs, Philip L. (29 July 2013).
"Picolinic acid" .
Catalytic Oxidation Reagents . Wiley Inc. p. 495ff.
ISBN
9781118704844 .
OCLC
954583821 .
^
a
b
c Grant, RS; Coggan, SE; Smythe, GA (2009).
"The physiological action of picolinic Acid in the human brain" . International Journal of Tryptophan Research . 2 : 71–9.
doi :
10.4137/ijtr.s2469 .
PMC
3195224 .
PMID
22084583 .
^ 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
978-3527306732 .
^ 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.
^ 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 .
^ Evans, Gary (1982).
"The Role of Picolinic Acid in Metal Metabolism" . Life Chemistry Reports . 1 . Harwood Academic Publishers: 57–67. Archived from
the original on 26 January 2016. Retrieved 20 March 2015 .
Receptor (
ligands )
GlyR Tooltip Glycine receptor
Positive modulators:
Alcohols (e.g.,
brometone ,
chlorobutanol (chloretone) ,
ethanol (alcohol) ,
tert -butanol (2M2P) ,
tribromoethanol ,
trichloroethanol ,
trifluoroethanol )
Alkylbenzene sulfonate
Anandamide
Barbiturates (e.g.,
pentobarbital ,
sodium thiopental )
Chlormethiazole
D12-116
Dihydropyridines (e.g.,
nicardipine )
Etomidate
Ginseng constituents (e.g.,
ginsenosides (e.g.,
ginsenoside-Rf ))
Glutamic acid (glutamate)
Ivermectin
Ketamine
Neuroactive steroids (e.g.,
alfaxolone ,
pregnenolone (eltanolone) ,
pregnenolone acetate ,
minaxolone ,
ORG-20599 )
Nitrous oxide
Penicillin G
Propofol
Tamoxifen
Tetrahydrocannabinol
Triclofos
Tropeines (e.g.,
atropine ,
bemesetron ,
cocaine ,
LY-278584 ,
tropisetron ,
zatosetron )
Volatiles /
gases (e.g.,
chloral hydrate ,
chloroform ,
desflurane ,
diethyl ether (ether) ,
enflurane ,
halothane ,
isoflurane ,
methoxyflurane ,
sevoflurane ,
toluene ,
trichloroethane (methyl chloroform) ,
trichloroethylene )
Xenon
Zinc
Antagonists:
2-Aminostrychnine
2-Nitrostrychnine
4-Phenyl-4-formyl-N-methylpiperidine
αEMBTL
Bicuculline
Brucine
Cacotheline
Caffeine
Colchicine
Colubrine
Cyanotriphenylborate
Dendrobine
Diaboline
Endocannabinoids (e.g.,
2-AG ,
anandamide (AEA) )
Gaboxadol (THIP)
Gelsemine
iso-THAZ
Isobutyric acid
Isonipecotic acid
Isostrychnine
Laudanosine
N-Methylbicuculline
N-Methylstrychnine
N,N-Dimethylmuscimol
Nipecotic acid
Pitrazepin
Pseudostrychnine
Quinolines (e.g.,
4-hydroxyquinoline ,
4-hydroxyquinoline-3-carboxylic acid ,
5,7-CIQA ,
7-CIQ ,
7-TFQ ,
7-TFQA )
RU-5135
Sinomenine
Strychnine
Thiocolchicoside
Tutin
Negative modulators:
Amiloride
Benzodiazepines (e.g.,
bromazepam ,
clonazepam ,
diazepam ,
flunitrazepam ,
flurazepam )
Corymine
Cyanotriphenylborate
Daidzein
Dihydropyridines (e.g.,
nicardipine ,
nifedipine ,
nitrendipine )
Furosemide
Genistein
Ginkgo constituents (e.g.,
bilobalide ,
ginkgolides (e.g.,
ginkgolide A ,
ginkgolide B ,
ginkgolide C ,
ginkgolide J ,
ginkgolide M ))
Imipramine
NBQX
Neuroactive steroids (e.g.,
3α-androsterone sulfate ,
3β-androsterone sulfate ,
deoxycorticosterone ,
DHEA sulfate ,
pregnenolone sulfate ,
progesterone )
Opioids (e.g.,
codeine ,
dextromethorphan ,
dextrorphan ,
levomethadone ,
levorphanol ,
morphine ,
oripavine ,
pethidine ,
thebaine )
Picrotoxin (i.e.,
picrotin and
picrotoxinin )
PMBA
Riluzole
Tropeines (e.g.,
bemesetron ,
LY-278584 ,
tropisetron ,
zatosetron )
Verapamil
Zinc
NMDAR Tooltip N-Methyl-D-aspartate receptor
Transporter (
blockers )
GlyT1 Tooltip Glycine transporter 1
GlyT2 Tooltip Glycine transporter 2