Article · Wikipedia archive · Last revised Jul 27, 2026

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. Fluorocitrate is a metabolite of fluoroacetic acid and is very toxic because it is not processable using aconitase in the citrate cycle. The enzyme is inhibited and the cycle stops working.

Last revised
Jul 27, 2026
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Source
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Fluorocitric acid
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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
3D model (JSmol)
ChemSpider
  • 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) checkY
    Key: DGXLYHAWEBCTRU-UHFFFAOYSA-N checkY
  • 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
  • O=C(O)C(O)(CC(=O)O)C(F)C(=O)O
Properties
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)
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).
checkY verify (what is checkYX markN ?)

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 Fluorocitrate 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

See also

See also

References

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