Quinolinic acid
Structural formula | ||||||||||||||||||||||
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General | ||||||||||||||||||||||
Surname | Quinolinic acid | |||||||||||||||||||||
other names |
Pyridine-2,3-dicarboxylic acid |
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Molecular formula | C 7 H 5 NO 4 | |||||||||||||||||||||
Brief description |
crystalline yellow powder, |
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properties | ||||||||||||||||||||||
Molar mass | 167.12 g mol −1 | |||||||||||||||||||||
Physical state |
firmly |
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Melting point |
Decomposition from 185–190 ° C |
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pK s value |
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solubility |
slightly soluble in water (10 g l −1 at 20 ° C) |
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safety instructions | ||||||||||||||||||||||
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Toxicological data | ||||||||||||||||||||||
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.