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Fluorocitric acid
Fluorocitric acid
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| Names
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| IUPAC name
3-C-Carboxy-2,4-dideoxy-2-fluoropentaric acid
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| Other names
2-Fluorocitric acid; 2-Fluorocitrate; 1-Fluoro-2-hydroxypropane-1,2,3-tricarboxylic acid
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| Identifiers
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| ChemSpider
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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)  YKey: DGXLYHAWEBCTRU-UHFFFAOYSA-N YInChI=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
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O=C(O)C(O)(CC(=O)O)C(F)C(=O)O
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| Properties
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HOC(CO2H)(CH2CO2H)(CHFCO2H)
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| Molar mass
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210.113 g·mol−1
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| Appearance
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Odorless, white crystals
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| Density
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1.37 g/cm3
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| Melting point
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35.2 °C (95.4 °F; 308.3 K)
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| Boiling point
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165 °C (329 °F; 438 K)
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Soluble
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| Hazards
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Main hazards
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
Chemical compound
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]
See also
References
- ^ 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)
- ^ 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
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