Quinolinic acid Chemical Properties

Melting point:

188-190 °C (dec.) (lit.)

Boiling point:

295.67°C (rough estimate)

Density 

1.5216 (rough estimate)

refractive index 

1.6280 (estimate)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

10g/l

pka

2.43(at 25℃)

form 

Crystalline Powder

color 

White to light yellow-beige

Odor

odorless

Water Solubility 

0.55 g/100 mL

Merck 

14,8073

BRN 

137110

InChIKey

GJAWHXHKYYXBSV-UHFFFAOYSA-N

CAS DataBase Reference

89-00-9(CAS DataBase Reference)

EPA Substance Registry System

2,3-Pyridinedicarboxylic acid (89-00-9)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38-33

Safety Statements 

26-36/37-24/25-37

WGK Germany 

3

RTECS 

US7967250

TSCA 

T

HazardClass 

IRRITANT

HS Code 

29333999

Hazardous Substances Data

89-00-9(Hazardous Substances Data)

Toxicity

Focal injection of quinolinic acid into specific areas of the brain produces neuronal damage although sparing axons of passage. Similarities between the biochemical and morphological profiles of these lesions and human neuropathy seen in neurodegenerative diseases have led to the proposal that endogenous excitotoxins may play a role in such neurodegenerative disease states. Quinolinic acid is an intermediate in the kynurenine pathway of tryptophan metabolism and has been detected in the brains of several mammals including man. The neuroexcitatory action is thought to be mediated via interaction with the N-methyl-D-aspartate (NMDA) receptor of the glutamate family. No mechanism for quinolinic acid removal, nor for synaptic inactivation, has been found, and consequently accumulation of concentrations capa_x0002_ble of inducing neuronal degeneration and death may occur.

MSDS

• Language:English Provider:Pyridine-2,3-dicarboxylic acid
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

Quinolinic acid Usage And Synthesis

Chemical Properties

White powder;Light yellow powder

Uses

An inhibitor of glucose synthesis.

Uses

A matabolite of tryptophan and a putative NMDA receptor agonist.

Uses

Inhibits glucose synthesis

Uses

Quinolinic acid is an endogenous NMDA agonist. Quinolinic acid is a metabolite of tryptophan that acts as a putative NMDA receptor agonist. Quinolinic acid is an ?excitotoxic? metabolite and an agonist of N-methyl-D-aspartate receptors. properties of KYNA raise the possibility of a functional link between KYNA and QUIN in the brain which may be of relevance for an understanding of human neurodegenerative disorders. Quinolinic acid is a potent endogenous excitant at amino acid receptors in CNS.

Definition

ChEBI: Quinolinic acid is a pyridinedicarboxylic acid that is pyridine substituted by carboxy groups at positions 2 and 3. It is a metabolite of tryptophan. It has a role as a NMDA receptor agonist, a human metabolite, a mouse metabolite and an Escherichia coli metabolite. It is a conjugate acid of a quinolinate(1-) and a quinolinate.

Biosynthesis

The 3-hydroxyanthranilic acid oxygenase (3-HAO) catalyzes the conversion of 3-hydroxyanthranilic acid (3-HA) acid to an unstable intermediate, aminocarboxymuconic semialdehyde, which then preferentially converts to QUIN by a nonenzymatic cyclisation. This intermediate compound can also produce picolinic acid instead of QUIN. Finally, QUIN is catabolized to NAD+ and carbon dioxide by the action of quinolinate phosphoribosyl transferase (QPRT). This enzyme has been identified in rat and human CNS tissue[1].

Synthesis Reference(s)

Journal of the American Chemical Society, 71, p. 3020, 1949 DOI: 10.1021/ja01177a021

Hazard

A poison by skin contact. Moderately toxic by ingestion. A mild skin irritant.

Industrial uses

The use of quinolinic acid during flotation of hematite results in the adsorption of quinoline on hematite, allowing amine to selectively adsorb onto the hematite surface.

Biological Activity

Endogenous NMDA agonist and transmitter candidate. May distinguish between NMDA receptor subtypes.

Biological Activity

Quinolinic acid (QA) is a 2,3-pyridine dicarboxylic acid (C7H5NO4). QA is produced following the metabolic breakdown of the amino acid tryptophan, via the kynurenine pathway. Tryptophan is able to cross the blood–brain barrier (BBB), and upon entering the brain, is taken up by astrocytes, macrophages, microglia, and dendtritic cells and converted into kynurenine. In the presence of the enzyme 3-hydroxyanthranilic acid, kynurenine is converted into QA through a series of enzymatic reactions. QA is normally present in extremely low, nanomolar concentrations in the brain and in cerebrospinal fluid and does not cause damage to the surrounding cells. Accumulation of endogenous QA has recently been implicated in the etiology of certain neurodegenerative diseases, especially those with a strong inflammatory component, such as Parkinson’s disease (PD), amyotrophic lateral sclerosis (ALS), Huntington’s disease (HD), Alzheimer’s disease (AD), stroke, multiple sclerosis (MS), and epilepsy[1].

Safety Profile

A poison by skin contact. Moderately toxic by ingestion. Experimental reproductive effects. A mdd skinn irritant. When heated to decomposition it emits toxic vapors of NOx.

storage

Room temperature

References

[1] Rafael Lugo-Huitrón. “Quinolinic acid: an endogenous neurotoxin with multiple targets.” Oxidative Medicine and Cellular Longevity (2013): 104024.

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