Fluorocitric acid

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Fluorocitric acid

IUPAC name 3-C-Carboxy-2,4-dideoxy-2-fluoropentaric acid
Other names 2-Fluorocitric acid; 2-Fluorocitrate; 1-Fluoro-2-hydroxypropane-1,2,3-tricarboxylic acid
Identifiers
CAS number	357-89-1^Y
PubChem	107647
ChemSpider	96829^Y
Jmol-3D images	Image 1
SMILES O=C(O)C(O)(CC(=O)O)C(F)C(=O)O
InChI InChI=1S/C6H7FO7/c7-3(4(10)11)6(14,5(12)13)1-2(8)9/h3,14H,1H2,(H,8,9)(H,10,11)(H,12,13)^Y Key: DGXLYHAWEBCTRU-UHFFFAOYSA-N^Y InChI=1/C6H7FO7/c7-3(4(10)11)6(14,5(12)13)1-2(8)9/h3,14H,1H2,(H,8,9)(H,10,11)(H,12,13) Key: DGXLYHAWEBCTRU-UHFFFAOYAE
Properties
Molecular formula	C₆H₇FO₇
Molar mass	210.11 g mol⁻¹
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Fluorocitric acid is a fluorinated carboxylic acid derived from citric acid by substitution of one hydrogen by a fluorine atom. The appropriate anion is called fluorocitrate. It is a metabolite of fluoroacetic acid and is very toxic because it is not processable using aconitase in the citrate cycle (where fluorocitrate takes place of citrate as the substrate). The enzyme is inhibited and the cycle stops working.^[1]

References

↑ Horák, J.; Linhart, I.; Klusoň, P. (2004). Úvod do toxikologie a ekologie pro chemiky (in Czech) (1st ed.). Prague: VŠCHT v Praze. ISBN 80-7080-548-X.

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