Chemistry:Cinchomeronic acid
From HandWiki
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| Names | |
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| 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 | |
| EC Number |
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| 487254 | |
PubChem CID
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| UNII | |
CompTox Dashboard (EPA)
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| 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 pictograms | 
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| GHS Signal word | Warning |
| HH315Script error: No such module "Preview warning".Category:GHS errors, HH319Script error: No such module "Preview warning".Category:GHS errors, HH335Script error: No such module "Preview warning".Category:GHS errors | |
| PP261Script error: No such module "Preview warning".Category:GHS errors, PP264Script error: No such module "Preview warning".Category:GHS errors, PP264+P265Script error: No such module "Preview warning".Category:GHS errors, PP271Script error: No such module "Preview warning".Category:GHS errors, PP280Script error: No such module "Preview warning".Category:GHS errors, PP302+P352Script error: No such module "Preview warning".Category:GHS errors, PP304+P340Script error: No such module "Preview warning".Category:GHS errors, PP305+P351+P338Script error: No such module "Preview warning".Category:GHS errors, PP319Script error: No such module "Preview warning".Category:GHS errors, PP321Script error: No such module "Preview warning".Category:GHS errors, PP332+P317Script error: No such module "Preview warning".Category:GHS errors, PP337+P317Script error: No such module "Preview warning".Category:GHS errors, PP362+P364Script error: No such module "Preview warning".Category:GHS errors, PP403+P233Script error: No such module "Preview warning".Category:GHS errors, PP405Script error: No such module "Preview warning".Category:GHS errors, PP501Script error: No such module "Preview warning".Category:GHS errors | |
| 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). | |
| Infobox references | |
Tracking categories (test):
Cinchomeronic acid is an organic compound with the molecular formula C
7H
5NO
4.[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
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
- ↑ 1.0 1.1 PubChem. "Cinchomeronic acid" (in en). https://pubchem.ncbi.nlm.nih.gov/compound/10273.
- ↑ 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. https://books.google.com/books?id=PtTuOXYBi3IC&pg=PA59. Retrieved 24 January 2026.
- ↑ Bernthsen, August (1889) (in en). A Text-book of Organic Chemistry. D. Van Nostrand Company. p. 488. https://books.google.com/books?id=qSNEAQAAMAAJ&dq=Cinchomeronic+acid&pg=PA488. Retrieved 24 January 2026.
- ↑ Wolffenstein, Richard (1922). Die Pflanzenalkaloide (3rd ed.). Berlin, Heidelberg: Springer Berlin Heidelberg. p. 66. ISBN 978-3-642-92449-1. https://books.google.com/books?id=0wKoBgAAQBAJ&pg=PA66. Retrieved 24 January 2026.
- ↑ (in en) Journal of the Chemical Society. Chemical Society (Great Britain). 1879. p. 947. https://books.google.com/books?id=k-qC4lp3izUC&dq=Cinchomeronic+acid&pg=PA947. 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. https://books.google.com/books?id=xykgFDOJvfcC&pg=PA706.
- ↑ 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" (in en). CrystEngComm 10 (10): 1404–1409. doi:10.1039/B807015F. ISSN 1466-8033. Bibcode: 2008CEG....10.1404E. https://pubs.rsc.org/en/Content/ArticleLanding/2008/CE/b807015f. Retrieved 24 January 2026.
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