Cinchomeronic acid

Last updated
Cinchomeronic acid
3,4-Pyridine Dicarboxylic Acid V.2.svg
Names
Preferred IUPAC name
pyridine-3,4-dicarboxylic acid
Other names
  • 3,4-Pyridinedicarboxylic acid
  • Chinchomeronic acid
  • NSC 178
Identifiers
3D model (JSmol)
137242
ChEBI
ChEMBL
ECHA InfoCard 100.007.006 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 207-705-4
PubChem CID
UNII
  • InChI=1S/C7H5NO4/c9-6(10)4-1-2-8-3-5(4)7(11)12/h1-3H,(H,9,10)(H,11,12)
    Key: MUYSADWCWFFZKR-UHFFFAOYSA-N
  • O=C(O)C=1C=NC=CC1C(=O)O
Properties
C7H5NO4
Molar mass 167.120 g·mol−1
Appearancepale yellow crystalline
Melting point 256 °C (493 °F; 529 K)
sparingly soluble
Hazards
GHS labelling: [1]
GHS-pictogram-exclam.svg
Warning
H315, H319, H335
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, P501
Related compounds
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Cinchomeronic acid is an organic compound with the molecular formula C7H5NO4. [1] The acid was initially isolated by Hugo Weidel in 1868. [2] The compound is one of six isomers of pyridinedicarboxylic acid that are dicarboxylic derivatives of pyridine. [3]

Contents

Synthesis

Cinchomeronic acid is obtained as a degradation product of various Cinchona alkaloids. For example, it is obtained from quinine, cinchonidine, cinchonine, and apoquinine using nitric acid or by oxidation of β-collidine, lepidine, or isoquinoline. [4] [5]

Cinchomeric acid can also be prepared by oxidation of isoquinoline with potassium permanganate. [6]

Physical properties

The acid forms white to pale yellow crystalline compound derived from Cinchona alkaloids. It demonstrates low solubility in water, but is more soluble in organic solvents.

It exhibits dimorphism. A conventional orthorhombic structure (called "Form I") and a newly found primitive monoclinic structure ("Form II", space group P21/c) exist. [7]

Uses

It is utilized as a precursor in the synthesis of pharmaceutical compounds and as a ligand in coordination chemistry.

References

  1. 1 2 PubChem. "Cinchomeronic acid". pubchem.ncbi.nlm.nih.gov. Retrieved 2026-01-25.
  2. ↑ Die wissenschaftliche Welt von gestern: die Preisträger des Ignaz L. Lieben-Preises 1865 - 1937 und des Richard Lieben-Preises 1912 - 1928 ; ein Kapitel österreichischer Wissenschaftsgeschichte in Kurzbiografien. Wien Köln Weimar: Böhlau. 2004. p. 59. ISBN   978-3-205-77303-0 . Retrieved 24 January 2026.
  3. ↑ Bernthsen, August (1889). A Text-book of Organic Chemistry. D. Van Nostrand Company. p. 488. Retrieved 24 January 2026.
  4. ↑ Wolffenstein, Richard (1922). Die Pflanzenalkaloide (3rd ed.). Berlin, Heidelberg: Springer Berlin Heidelberg. p. 66. ISBN   978-3-642-92449-1 . Retrieved 24 January 2026.{{cite book}}: ISBN / Date incompatibility (help)
  5. ↑ Journal of the Chemical Society. Chemical Society (Great Britain). 1879. p. 947. Retrieved 24 January 2026.
  6. ↑ Breitmaier, Eberhard; Jung, Günther (2014). Organische Chemie, 7. vollst. Überarb. u. erw. Auflage 2012: Grundlagen,Verbindungsklassen, Reaktionen, Konzepte, Molekülstruktur, Naturstoffe, Syntheseplanung, Nachhaltigkeit (7., vollständig überarbeitete und erweiterte Auflage ed.). Stuttgart: Thieme. p. 706. ISBN   3-13-159987-1.
  7. ↑ Evans, Ivana Radosavljevic; Howard, Judith A. K.; Evans, John S. O.; Postlethwaite, Stella R.; Johnson, Mark R. (8 September 2008). "Polymorphism and hydrogen bonding in cinchomeronic acid: a variable temperature experimental and computational study". CrystEngComm . 10 (10): 1404–1409. doi:10.1039/B807015F. ISSN   1466-8033 . Retrieved 24 January 2026.
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