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 ;
3D model (JSmol)	Interactive image;
ChemSpider	96829 ;
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) Key: DGXLYHAWEBCTRU-UHFFFAOYSA-N ; 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(CO; 2H)(CH; 2CO; 2H)(CHFCO; 2H)
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
Main hazards	50px50px
	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

Fluorocitric acid is an organic compound with the chemical formula H O C(CO
2H)(CH
2CO
2H)(CHFCO
2H). 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]

References

↑ H., Garrett, Reginald (2013). Biochemistry. Grisham, Charles M. (5th ed.). Belmont, CA: Brooks/Cole, Cengage Learning. ISBN 9781133106296. OCLC 777722371.
↑ Horák, J.; Linhart, I.; Klusoň, P. (2004) (in Czech). Úvod do toxikologie a ekologie pro chemiky (1st ed.). Prague: VŠCHT v Praze. ISBN 80-7080-548-X.

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