Chemistry: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	210.113 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).
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Infobox references

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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. 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. 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.

See also

• Citric acid
• Fluoroacetic acid
• Citrate cycle

External links

• PubChem: Fluorocitrate
• Human Metabolome Database (HMDB): Fluorocitric acid
• The Chemical and Biochemical Properties of Fluorocitric Acid Pdf