2,3-Pyridinedicarboxylic acid
Product Information
Molecular Formula
C7H5NO4
Molecular Weight
167.12
Description
Quinolinic acid is an endogenous NMDA agonist and transmitter candidate. It may distinguish between NMDA receptor subtypes. By overactivating NMDA receptors, quinolinic acid produces neurotoxicity, which has been implicated in certain neurodegenerative disorders.
Synonyms
pyridine-2,3-dicarboxylic acid
IUPAC Name
pyridine-2,3-dicarboxylic acid
SMILES
C1=CC(=C(N=C1)C(=O)O)C(=O)O
InChI
InChI=1S/C7H5NO4/c9-6(10)4-2-1-3-8-5(4)7(11)12/h1-3H,(H,9,10)(H,11,12)
InChI Key
GJAWHXHKYYXBSV-UHFFFAOYSA-N
Boiling Point
425 °C at 760 mmHg
Melting Point
188 °C
Purity
99 %
Density
1.551 g/cm3
Solubility
Soluble in 180 parts water, in alkalies, slightly in alcohol. Almost insol in ether or benzene.
Appearance
White solid
Application
A metabolite of tryptophan; Used to make Assert (herbicide) and nicotinic acid.
Storage
Store in a cool and dry place (or refer to the Certificate of Analysis).
Refractive Index
1.62
LogP
0.47800
Vapor Pressure
0.0000061 [mmHg]
Henry's Law Constant
2.86X10-15 atm-cu m/mol at 25 °C (est)
Dissociation Constants
2.43
Odor
Odorless
Safety Information
Hazards
H315:
Causes skin irritation.
H319:
Causes serious eye irritation.
Causes skin irritation.
H319:
Causes serious eye irritation.
Precautionary Statement
P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, and P501
Signal Word
Warning
Computed Properties
XLogP3
0.2
Hydrogen Bond Donor Count
2
Hydrogen Bond Acceptor Count
5
Rotatable Bond Count
2
Exact Mass
167.02185764 g/mol
Monoisotopic Mass
167.02185764 g/mol
Topological Polar Surface Area
87.5Ų
Heavy Atom Count
12
Formal Charge
0
Complexity
204
Isotope Atom Count
0
Defined Atom Stereocenter Count
0
Undefined Atom Stereocenter Count
0
Defined Bond Stereocenter Count
0
Undefined Bond Stereocenter Count
0
Covalently-Bonded Unit Count
1
Compound Is Canonicalized
Yes
Patents
| Publication Number | Title | Priority Date |
|---|---|---|
| CN-114122407-A | Preparation method and application of bi-carbon layer-protected bismuth nanoparticle composite material | 2022-01-27 |
| CN-113912604-A | Compound with IDO inhibitory activity, preparation method, composition and application thereof | 2021-12-16 |
| CN-113979935-A | 2-aryl ureido-N- (4-fluorobenzyl) nicotinamide compound and application thereof | 2021-12-13 |
| CN-113979936-A | 2-aryl ureido-N- [3- (4-morpholinyl) propyl ] nicotinamide compound and application thereof | 2021-12-13 |
| CN-114057635-A | 2-aryl ureido-N- [2- (2-methoxyphenoxy) ethyl ] nicotinamide compound and application thereof | 2021-12-13 |
| CN-113979933-A | Preparation method of 4-chloropyridine-2, 6-diformyl chloride | 2021-11-29 |
| CN-113999174-A | Preparation method of quinoline-6-carboxylic acid | 2021-11-26 |
| CN-114047267-A | Method for analyzing nicotinic acid in tobacco root system by derivatization-gas chromatography-mass spectrometry | 2021-11-15 |
| CN-114105860-A | Catalytic asymmetric synthesis method and application of chiral oxindole spiro-analogue | 2021-11-12 |
| CN-113846180-A | Molecular marker nicas1 for identifying high and low nicotine content in tobacco, kit and application thereof | 2021-11-10 |
Literatures
| PMID | Publication Date | Title | Journal |
|---|---|---|---|
| 31678113 | 2020-01-05 | Pyridine-2,3-dicarboxylate, quinolinic acid, induces 1N4R Tau amyloid aggregation in vitro: Another evidence for the detrimental effect of the inescapable endogenous neurotoxin | Chemico-biological interactions |
| 30876764 | 2019-07-01 | Acute expression of the transcription factor Nrf2 after treatment with quinolinic acid is not induced by oxidative stress in the rat striatum | Neurotoxicology |
| 30130594 | 2018-11-01 | Neuroprotective effect of naringin, a flavone glycoside in quinolinic acid-induced neurotoxicity: Possible role of PPAR-γ, Bax/Bcl-2, and caspase-3 | Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association |
| 29981346 | 2018-09-01 | Effect of wedelolactone and gallic acid on quinolinic acid-induced neurotoxicity and impaired motor function: significance to sporadic amyotrophic lateral sclerosis | Neurotoxicology |
| 29702159 | 2018-07-01 | Quinolinic acid and glutamatergic neurodegeneration in Caenorhabditis elegans | Neurotoxicology |
| 28336214 | 2017-05-15 | Indoleamine 2,3-dioxygenase 1 (IDO1) inhibitors activate the aryl hydrocarbon receptor | Toxicology and applied pharmacology |
| 24211709 | 2014-01-01 | The specific PKR inhibitor C16 prevents apoptosis and IL-1β production in an acute excitotoxic rat model with a neuroinflammatory component | Neurochemistry international |
| 23571415 | 2013-06-01 | Structure-based identification of OATP1B1/3 inhibitors | Molecular pharmacology |
| 22939820 | 2012-12-15 | The kynurenine pathway in neurodegenerative diseases: mechanistic and therapeutic considerations | Journal of the neurological sciences |
| 22749004 | 2012-11-15 | Mitochondrial disturbances, excitotoxicity, neuroinflammation and kynurenines: novel therapeutic strategies for neurodegenerative disorders | Journal of the neurological sciences |
