Fluorocitric acid

Fluorocitric acid is an organic compound with the chemical formula HOC(CO₂H)(CH₂CO₂H)(CHFCO₂H). It is a fluorinated carboxylic acid derived from citric acid by substitution of one methylene hydrogen by a fluorine atom. The appropriate anion is called fluorocitrate. Fluorocitrate is formed in two steps from fluoroacetate. Fluoroacetate is first converted to fluoroacetyl-CoA by acetyl-CoA synthetase in the mitochondria. Then fluoroacetyl-CoA condenses with oxaloacetate to form fluorocitrate. This step is catalyzed by citrate synthase.^[1] Flurocitrate 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.^[2]

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
CompTox Dashboard (EPA)	DTXSID80957104
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	HOC(CO2H)(CH2CO2H)(CHFCO2H)
Molar mass	210.113 g·mol−1
Appearance	Odorless, white crystals
Density	1.37 g/cm3
Melting point	35.2 °C (95.4 °F; 308.3 K)
Boiling point	165 °C (329 °F; 438 K)
Solubility in water	Soluble
Hazards
Occupational safety and health (OHS/OSH):
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

See also

• Citric acid
• Fluoroacetic acid
• Citrate cycle

References

1. H., Garrett, Reginald (2013). Biochemistry. Grisham, Charles M. (5th ed.). Belmont, CA: Brooks/Cole, Cengage Learning. ISBN 9781133106296. OCLC 777722371.{{cite book}}: CS1 maint: multiple names: authors list (link)
2. 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.

External links

• PubChem: Fluorocitrate
• Human Metabolome Database (HMDB): Fluorocitric acid Archived 2016-03-04 at the Wayback Machine
• The Chemical and Biochemical Properties of Fluorocitric Acid Pdf