Cinchomeronic acid
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| Names | |
|---|---|
| Preferred IUPAC name
pyridine-3,4-dicarboxylic acid | |
Other names
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| Identifiers | |
3D model (JSmol) |
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| 137242 | |
| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.007.006 |
| EC Number |
|
| 487254 | |
PubChem CID |
|
| UNII | |
CompTox Dashboard (EPA) |
|
| |
| |
| Properties | |
| C7H5NO4 | |
| Molar mass | 167.120 g·mol−1 |
| Appearance | pale yellow crystalline |
| Melting point | 256 °C (493 °F; 529 K) |
| sparingly soluble | |
| Hazards | |
| GHS labelling:[1] | |
 | |
| 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 |
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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]
Synthesis
[edit]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
[edit]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
[edit]It is utilized as a precursor in the synthesis of pharmaceutical compounds and as a ligand in coordination chemistry.
References
[edit]- 1 2 PubChem. "Cinchomeronic acid". pubchem.ncbi.nlm.nih.gov. Retrieved 2026-01-25.
- ↑ 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.
- ↑ Bernthsen, August (1889). A Text-book of Organic Chemistry. D. Van Nostrand Company. p. 488. Retrieved 24 January 2026.
- ↑ 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) - ↑ Journal of the Chemical Society. Chemical Society (Great Britain). 1879. p. 947. Retrieved 24 January 2026.
- ↑ 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 978-3-13-159987-2.
- ↑ 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. Bibcode:2008CEG....10.1404E. doi:10.1039/B807015F. ISSN 1466-8033. Retrieved 24 January 2026.