Cinchomeronic acid

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Structural formula
Structural formula of cinchomeronic acid
General
Surname Cinchomeronic acid
other names
  • 3,4-pyridinedicarboxylic acid
  • Pyridine-3,4-dicarboxylic acid
Molecular formula C 7 H 5 NO 4
Brief description

white to beige solid

External identifiers / databases
CAS number 490-11-9
ECHA InfoCard 100.007.006
PubChem 10273
ChemSpider 9854
Wikidata Q27120712
properties
Molar mass 167.12 g mol −1
Physical state

firmly

Melting point

262 ° C (decomposition)

solubility
  • slightly soluble in water (2.34 g l −1 at 25 ° C)
  • practically insoluble in diethyl ether
safety instructions
GHS labeling of hazardous substances
07 - Warning

Caution

H and P phrases H: 315-319-335
P: 261-305 + 351 + 338
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Cinchomeronic acid is a chemical compound from the group of pyridinedicarboxylic acids . It was first verified by Hugo Weidel in 1868 .

Occurrence

Cinchomeronic is an intermediate of nicotinic acid - biosynthesis in bacteria.

Extraction and presentation

Cinchomeronic acid is obtained in particular as a breakdown product of various china alkaloids. For example, from quinine , cinchonidine , cinchonine and apoquinine by means of nitric acid or by oxidation of cinchonidic acid , β-collodine , lepidine or isoquinoline .

Cinchomeronic acid can be prepared by the oxidation of isoquinoline with potassium permanganate .

properties

Cinchomeronic acid is a white to beige solid that is sparingly soluble in water.

Individual evidence

  1. ↑ a b c Datasheet Cinchomeronic Acid (PDF) from Merck , accessed on January 2, 2019.
  2. ↑ a b c d e f data sheet 3,4-Pyridinedicarboxylic acid, 97% from Sigma-Aldrich , accessed on January 2, 2019 ( PDF ).
  3. ↑ a b c d Richard Wolffenstein: The plant alkaloids . Springer-Verlag, 2013, ISBN 978-3-642-92449-1 , pp. 66 ( limited preview in Google Book search).
  4. ^ W. Gerhard Pohl: The scientific world of yesterday, the winners of the Ignaz L. Lieben Prize 1865-1937 and the Richard Lieben Prize 1912-1928: a chapter of Austrian scientific history in short biographies . Böhlau Verlag Vienna, 2004, ISBN 978-3-205-77303-0 , p. 59 ( limited preview in Google Book search).
  5. ↑ F. Lingens: Cinchomeronic acid, intermediate product of nicotinic acid biosynthesis in bacteria. In: Angewandte Chemie. 72, 1960, p. 920, doi : 10.1002 / anie.19600722319 .
  6. ↑ Eberhard Breitmaier, Günther Jung: Organic Chemistry, 7th complete revision. u. exp. Edition 2012 Basics, classes of compounds, reactions, concepts, molecular structure, natural substances, synthesis planning, sustainability . Georg Thieme Verlag, 2014, ISBN 3-13-159987-1 , p. 706 ( limited preview in Google Book search).