Fluorocitric acid

Fluorocitric acid
Names

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
3D model (JSmol)	Interactive image
ChemSpider	96829^Y
PubChem CID	107647
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
SMILES O=C(O)C(O)(CC(=O)O)C(F)C(=O)O
Properties
Chemical formula	C₆H₇FO₇
Molar mass	210.11 g·mol⁻¹
Appearance	Odorless, white crystals
Density	1.37
Melting point	35.2°C
Boiling point	165°C
Solubility in water	Soluble
Hazards
Main hazards
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y verify (what is ^YN ?)
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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