Pyridin-2,3-dicarbonsure

Bezeichnung:Pyridin-2,3-dicarbonsure

CAS-Nr89-00-9

Englisch Name:Quinolinic acid

CBNumberCB7316162

SummenformelC7H5NO4

Molgewicht167.12

MOL-Datei89-00-9.mol

Synonyma

Pyridin-2,3-dicarbonsure

Pyridin-2,3-dicarbonsure physikalisch-chemischer Eigenschaften

Schmelzpunkt	188-190 °C (dec.) (lit.)
Siedepunkt	295.67°C (rough estimate)
Dichte	1.5216 (rough estimate)
Brechungsindex	1.6280 (estimate)
storage temp.	Keep in dark place,Sealed in dry,Room Temperature
Löslichkeit	10g/l
Aggregatzustand	Crystalline Powder
pka	2.43(at 25℃)
Farbe	White to light yellow-beige
Geruch (Odor)	odorless
Wasserlöslichkeit	0.55 g/100 mL
Merck	14,8073
BRN	137110
InChIKey	GJAWHXHKYYXBSV-UHFFFAOYSA-N
CAS Datenbank	89-00-9(CAS DataBase Reference)
EPA chemische Informationen	2,3-Pyridinedicarboxylic acid (89-00-9)

Sicherheit

Kennzeichnung gefährlicher	Xi
R-Sätze:	36/37/38-33
S-Sätze:	26-36/37-24/25-37
WGK Germany	3
RTECS-Nr.	US7967250
TSCA	T
HazardClass	IRRITANT
HS Code	29333999
Giftige Stoffe Daten	89-00-9(Hazardous Substances Data)
Toxizität	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.

Gefahreninformationscode (GHS)

Quinolinic acid Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
R33:Gefahr kumulativer Wirkungen.
S-Sätze Betriebsanweisung:
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S36/37:Bei der Arbeit geeignete Schutzhandschuhe und Schutzkleidung tragen.
S24/25:Berührung mit den Augen und der Haut vermeiden.
S37:Geeignete Schutzhandschuhe tragen.
Chemische Eigenschaften
White powder;Light yellow powder
Verwenden
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.
Verwenden
A matabolite of tryptophan and a putative NMDA receptor agonist.
Verwenden
An inhibitor of glucose synthesis.
Verwenden
Inhibits glucose synthesis
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.
Biosynthese
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.
Industrielle Verwendung
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.
Biologische Aktivität
Endogenous NMDA agonist and transmitter candidate. May distinguish between NMDA receptor subtypes.
Biologische Aktivität
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].
Sicherheitsprofil
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.
Lager
Room temperature
Einzelnachweise
[1] Rafael Lugo-Huitrón. “Quinolinic acid: an endogenous neurotoxin with multiple targets.” Oxidative Medicine and Cellular Longevity (2013): 104024.

Quinolinic acid Upstream-Materialien And Downstream Produkte

Pyridin-2,3-dicarbonsure Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

89-00-9, Quinolinic acid Verwandte Suche:

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