Quinolinic acid

Structural formula
General
Surname	Quinolinic acid
other names	Pyridine-2,3-dicarboxylic acid
Molecular formula	C 7 H 5 NO 4
Brief description	crystalline yellow powder,
External identifiers / databases
EC number	201-874-8
ECHA InfoCard	100.001.704
PubChem	1066
ChemSpider	1037
DrugBank	DB01796
Wikidata	Q411945
properties
Molar mass	167.12 g mol −1
Physical state	firmly
Melting point	Decomposition from 185–190 ° C
pK s value	pK s 1 (25 ° C) = 2.41; pK s 2 (25 ° C) = 5.05;
solubility	slightly soluble in water (10 g l −1 at 20 ° C)
safety instructions
GHS labeling of hazardous substances Caution
H and P phrases	H: 319-335
	P: 305 + 351 + 338
Toxicological data	> 500 mg kg −1 ( LD 50 , rat , oral )
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Quinoline acid ( pyridine-2,3-dicarboxylic acid ) is a chemical compound from the group of pyridinedicarboxylic acids . It consists of a pyridine ring that has carboxy groups in the 2- and 3-position .

Occurrence

Quinolinic acid occurs naturally as a metabolite of tryptophan .

Extraction and presentation

Quinolinic acid can be prepared by electrochemical oxidation of quinoline or with the help of hydrogen peroxide .

Alternatively, it can be prepared from quinoline by oxidation using potassium permanganate (KMnO ₄ ). It is produced as an intermediate in the synthesis of nicotinic acid . From 185–190 ° C, quinolinic acid decomposes to nicotinic acid by decarboxylation .

Individual evidence

↑ ^a ^b ^c ^d ^e data sheet pyridine-2,3-dicarboxylic acid (PDF) from Merck , accessed on December 27, 2019.
^ ^A ^b D'Ans-Lax: Pocket book for chemists and physicists , 3rd edition, Volume 1, Springer-Verlag, Berlin-Göttingen-Heidelberg 1967 ( ChemieOnline - pK _b and pK _s values ).
↑ Quinolinic acid data sheet from AlfaAesar, accessed on December 27, 2019 ( PDF )(JavaScript required) .

↑ U. Dettmer, M. Folkerts, E. Kächler, A. Sönnichsen: Intensive Course in Biochemistry , 1st edition, Elsevier Verlag, Munich 2005, ISBN 3-437-44450-6 , p. 193.

↑ Patent: Electrochemical oxidation of pyridine bases; Toomey Jr., Joseph E .; Reilly Industries, Inc.

↑ Patent application US4420616 : Oxidative process for the preparation of copper quinolinate. Applied on February 20, 1981 , published on December 13, 1983 , applicant: YAMAMOTO KAGAKU GOSEI KK, inventor: IKEGAMI, SEISHI; HATANO, YOSHIHIRO. ‌

^ Andrew Streitwieser, Clayton H. Heathcock and Edward M. Kosower: Organic Chemistry , 2nd Edition, Wiley-VCH, Weinheim 1994, ISBN 3-527-29005-2 ; P. 1227.

[M_23-1] ↑ ^a ^b ^c ^d ^e data sheet pyridine-2,3-dicarboxylic acid (PDF) from Merck , accessed on December 27, 2019.

[D'Ans-Lax-2] A ^b D'Ans-Lax: Pocket book for chemists and physicists , 3rd edition, Volume 1, Springer-Verlag, Berlin-Göttingen-Heidelberg 1967 ( ChemieOnline - pK _b and pK _s values ).

[BSL-3] Quinolinic acid data sheet from AlfaAesar, accessed on December 27, 2019 ( PDF )(JavaScript required) .

[4] U. Dettmer, M. Folkerts, E. Kächler, A. Sönnichsen: Intensive Course in Biochemistry , 1st edition, Elsevier Verlag, Munich 2005, ISBN 3-437-44450-6 , p. 193.

[5] Patent: Electrochemical oxidation of pyridine bases; Toomey Jr., Joseph E .; Reilly Industries, Inc.

[6] Patent application US4420616 : Oxidative process for the preparation of copper quinolinate. Applied on February 20, 1981 , published on December 13, 1983 , applicant: YAMAMOTO KAGAKU GOSEI KK, inventor: IKEGAMI, SEISHI; HATANO, YOSHIHIRO. ‌

[OC-7] Andrew Streitwieser, Clayton H. Heathcock and Edward M. Kosower: Organic Chemistry , 2nd Edition, Wiley-VCH, Weinheim 1994, ISBN 3-527-29005-2 ; P. 1227.