Jump to content

Fluorocitric acid: Difference between revisions

Page 1
Page 2
Content deleted Content added
CheMoBot (talk | contribs)
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
The word "fluorinated" refers to "fluorination", not to "fluorine"
 
(38 intermediate revisions by 23 users not shown)
Line 1: Line 1:
{{Chembox
{{Chembox
| Watchedfields = changed
| verifiedrevid = 445847233
| verifiedrevid = 445849101
| ImageFile = Fluorocitric acid.svg
| ImageFile = Fluorocitric acid.svg
| ImageSize = 200px
| ImageSize = 200px
| IUPACName = 3-''C''-Carboxy-2,4-dideoxy-2-fluoropentaric acid
| IUPACName = 3-''C''-Carboxy-2,4-dideoxy-2-fluoropentaric acid
| 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
| Section1 = {{Chembox Identifiers
|Section1={{Chembox Identifiers
| CASNo = 357-89-1
| CASNo = 357-89-1
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo_Ref = {{cascite|correct|CAS}}
| PubChem = 107647
| PubChem = 107647
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 96829
| ChemSpiderID = 96829
| SMILES = O=C(O)C(O)(CC(=O)O)C(F)C(=O)O
| SMILES = O=C(O)C(O)(CC(=O)O)C(F)C(=O)O
| 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)
| 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)
| InChIKey = DGXLYHAWEBCTRU-UHFFFAOYAE
| InChIKey = DGXLYHAWEBCTRU-UHFFFAOYAE
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| 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)
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = DGXLYHAWEBCTRU-UHFFFAOYSA-N
| StdInChIKey = DGXLYHAWEBCTRU-UHFFFAOYSA-N
}}
}}
| Section2 = {{Chembox Properties
|Section2={{Chembox Properties
| Formula = {{chem2|HOC(CO2H)(CH2CO2H)(CHFCO2H)}}
| C=6|H=7|F=1|O=7
| C=6 | H=7 | F=1 | O=7
| Appearance =
| Appearance = Odorless, white crystals
| Density =
| Density = 1.37 g/cm<sup>3</sup>
| MeltingPt =
| BoilingPt =
| MeltingPtC = 35.2
| Solubility =
| BoilingPtC = 165
| Solubility = Soluble
}}
}}
| Section3 = {{Chembox Hazards
|Section3={{Chembox Hazards
| MainHazards =
| MainHazards = [[File:GHS-pictogram-skull.svg|50px]][[File:GHS-pictogram-pollu.svg|50px]]
| FlashPt =
| Autoignition =
| FlashPt =
| AutoignitionPt =
}}
}}
}}
}}


'''Fluorocitric acid''' is a [[Fluorine|fluorinated]] [[carboxylic acid]] derived from [[citric acid]] by [[Substituent|substitution]] of one [[hydrogen]] by a fluorine [[atom]]. The appropriate [[anion]] is called '''fluorocitrate'''. It 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 [[Inhibition|inhibited]] and the cycle stops working.<ref>{{cite book|last=Horák|first=J.|last2=Linhart|first2=I.|last3=Klusoň|first3=P.|title=Úvod do toxikologie a ekologie pro chemiky|edition=1st|publisher=VŠCHT v Praze|location=Prague|year=2004|isbn=807080548X|language=Czech}}</ref>
'''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>


== See also ==
== See also ==
Line 42: Line 44:


== References ==
== References ==
{{reflist}}
<references />


== External links ==
{{organic-compound-stub}}
*[https://pubchem.ncbi.nlm.nih.gov/compound/107647#section=Top PubChem: Fluorocitrate]
*[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}}
*[https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1205391/pdf/biochemj01003-0219.pdf The Chemical and Biochemical Properties of Fluorocitric Acid] Pdf


[[Category:Tricarboxylic acids]]
[[Category:Tricarboxylic acids]]
[[Category:Organofluorides]]
[[Category:Organofluorides]]
[[Category:Fluorohydrins]]
[[Category:Respiratory toxins]]
[[Category:Aconitase inhibitors]]
[[Category:Fluorinated carboxylic acids]]


{{organic-compound-stub}}
[[cs:Kyselina fluorcitronová]]