Berberonic acid

Berberonic acid

Names
Preferred IUPAC name Pyridine-2,4,5-tricarboxylic acid
Other names 2,4,5-Pyridinetricarboxylic acid
Identifiers
CAS Number	490-28-8
3D model (JSmol)	Interactive image
ChemSpider	9075159
PubChem CID	10899899
UNII	HDZ7RH33XB  Y
CompTox Dashboard (EPA)	DTXSID401302807
InChI InChI=1S/C8H5NO6/c10-6(11)3-1-5(8(14)15)9-2-4(3)7(12)13/h1-2H,(H,10,11)(H,12,13)(H,14,15) Key: IFLXVSWHQQZRQI-UHFFFAOYSA-N
SMILES C1=C(C(=CN=C1C(=O)O)C(=O)O)C(=O)O
Properties
Chemical formula	C8H5NO6
Molar mass	211.129 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Berberonic acid (pyridine-2,4,5-tricarboxylic acid) is an organic compound that belongs to the heterocycles (more precisely the heteroaromatics). It belongs to the group of pyridinetricarboxylic acids and consists of a pyridine ring which carries three carboxy groups in the 2-, 4- and 5-positions. The name is derived from berberine.

Preparation

Berberonic acid is obtained in the oxidation of berberine with nitric acid. ^[1] It can also be derived by oxidative degradation of monascaminone with potassium permanganate. ^[2]

References

1. Wolffenstein, Richard (1922). Die Pflanzenalkaloide (in German) (3rd ed.). Berlin, Heidelberg. pp. 69–72. ISBN   978-3-642-92449-1. OCLC   913710178.
2. Kumasaki, S.; Nakanishi, K.; Nishikawa, E.; Ohashi, M. (1962). "Structure of Monascorubrin". Tetrahedron. 18 (10): 1171–1184. doi:10.1016/S0040-4020(01)99285-3.