Fluorocitric acid: Difference between revisions
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Updating {{chembox}} (no changed fields - added verified revid - updated 'ChemSpiderID_Ref', 'DrugBank_Ref', 'UNII_Ref', 'ChEMBL_Ref', 'ChEBI_Ref', 'KEGG_Ref', 'StdInChI_Ref', 'StdInChIKey_Ref', 'ChEBI_Ref') per [[Wikipedia:WikiProject Chemicals/Chem |
Bernardirfan (talk | contribs) The word "fluorinated" refers to "fluorination", not to "fluorine" |
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{{Chembox |
{{Chembox |
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| Watchedfields = changed |
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| verifiedrevid = |
| verifiedrevid = 445849101 |
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| ImageFile = Fluorocitric acid.svg |
| ImageFile = Fluorocitric acid.svg |
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| ImageSize = 200px |
| ImageSize = 200px |
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| IUPACName = 3-''C''-Carboxy-2,4-dideoxy-2-fluoropentaric acid |
| IUPACName = 3-''C''-Carboxy-2,4-dideoxy-2-fluoropentaric acid |
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| OtherNames = 1-Fluoro-2-hydroxypropane-1,2,3-tricarboxylic acid |
| OtherNames = 2-Fluorocitric acid; 2-Fluorocitrate; 1-Fluoro-2-hydroxypropane-1,2,3-tricarboxylic acid |
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|Section1={{Chembox Identifiers |
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| CASNo = 357-89-1 |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| PubChem = 107647 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 96829 |
| ChemSpiderID = 96829 |
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| SMILES = O=C(O)C(O)(CC(=O)O)C(F)C(=O)O |
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| 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) |
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| InChIKey = DGXLYHAWEBCTRU-UHFFFAOYAE |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 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) |
| StdInChI = 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) |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = DGXLYHAWEBCTRU-UHFFFAOYSA-N |
| StdInChIKey = DGXLYHAWEBCTRU-UHFFFAOYSA-N |
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}} |
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|Section2={{Chembox Properties |
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| Formula = {{chem2|HOC(CO2H)(CH2CO2H)(CHFCO2H)}} |
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| C=6 | H=7 | F=1 | O=7 |
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| Appearance = |
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| Appearance = Odorless, white crystals |
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| Density = |
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| Density = 1.37 g/cm<sup>3</sup> |
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| MeltingPt = |
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| MeltingPtC = 35.2 |
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| BoilingPtC = 165 |
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| Solubility = Soluble |
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}} |
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|Section3={{Chembox Hazards |
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| MainHazards = |
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| MainHazards = [[File:GHS-pictogram-skull.svg|50px]][[File:GHS-pictogram-pollu.svg|50px]] |
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| FlashPt = |
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| FlashPt = |
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| AutoignitionPt = |
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'''Fluorocitric acid''' is |
'''Fluorocitric acid''' is an [[organic compound]] with the [[chemical formula]] {{chem2|HOC(CO2H)(CH2CO2H)(CHFCO2H)|auto=1}}. It is a [[fluorinated]] [[carboxylic acid]] derived from [[citric acid]] by [[Substituent|substitution]] of one [[Methylene group|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 [[Oxaloacetic acid|oxaloacetate]] to form fluorocitrate. This step is [[catalyzed]] by [[citrate synthase]].<ref>{{Cite book|title=Biochemistry|last=H.|first=Garrett, Reginald|date=2013|publisher=Brooks/Cole, Cengage Learning|others=Grisham, Charles M.|isbn=9781133106296|edition=5th|location=Belmont, CA|oclc=777722371}}</ref> 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 (biochemistry)|substrate]]). The [[enzyme]] is [[Enzyme inhibitor|inhibited]] and the cycle stops working.<ref>{{cite book | last1 = Horák | first1 = J. | last2 = Linhart | first2 = I. | last3 = Klusoň |first3 = P. | title = Úvod do toxikologie a ekologie pro chemiky | language = Czech | edition = 1st | publisher = VŠCHT v Praze | location = Prague | year = 2004 | isbn = 80-7080-548-X}}</ref> |
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== See also == |
== See also == |
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== References == |
== References == |
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{{reflist}} |
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<references /> |
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== External links == |
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*[https://pubchem.ncbi.nlm.nih.gov/compound/107647#section=Top PubChem: Fluorocitrate] |
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*[http://www.hmdb.ca/metabolites/HMDB31255 Human Metabolome Database (HMDB): Fluorocitric acid] {{Webarchive|url=https://web.archive.org/web/20160304054925/http://www.hmdb.ca/metabolites/HMDB31255 |date=2016-03-04}} |
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*[https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1205391/pdf/biochemj01003-0219.pdf The Chemical and Biochemical Properties of Fluorocitric Acid] Pdf |
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[[Category:Tricarboxylic acids]] |
[[Category:Tricarboxylic acids]] |
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[[Category:Organofluorides]] |
[[Category:Organofluorides]] |
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[[Category:Fluorohydrins]] |
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[[Category:Respiratory toxins]] |
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[[Category:Aconitase inhibitors]] |
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[[Category:Fluorinated carboxylic acids]] |
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[[cs:Kyselina fluorcitronová]] |