Cinchomeronic acid

Cinchomeronic acid
Names
	Preferred IUPAC name pyridine-3,4-dicarboxylic acid
	Other names 3,4-Pyridinedicarboxylic acid; Chinchomeronic acid; NSC 178;
Identifiers
CAS Number	490-11-9 ;
3D model (JSmol)	Interactive image;
Beilstein Reference	137242
ChEBI	CHEBI:46860;
ChEMBL	ChEMBL261326;
ChemSpider	9854;
ECHA InfoCard	100.007.006
EC Number	207-705-4;
Gmelin Reference	487254
PubChem CID	10273;
UNII	7389UZW5DY;
CompTox Dashboard (EPA)	DTXSID70197653;
	InChI 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;
	SMILES O=C(O)C=1C=NC=CC1C(=O)O;
Properties
Chemical formula	C7H5NO4
Molar mass	167.120 g·mol−1
Appearance	pale yellow crystalline
Melting point	256 °C (493 °F; 529 K)
Solubility in water	sparingly soluble
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H315, H319, H335
Precautionary statements	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	Quinolinic acid; Lutidinic acid; Isocinchomeronic acid; Dipicolinic acid; Dinicotinic acid;
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

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

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

^ ^a ^b 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.

[PubChem-1] 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 978-3-13-159987-2.

[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. Bibcode:2008CEG....10.1404E. doi:10.1039/B807015F. ISSN 1466-8033. Retrieved 24 January 2026.

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