| Revision as of 05:31, 17 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 466679288 of page Alpha-Ketobutyric_acid for the Chem/Drugbox validation project (updated: ''). |
Latest revision as of 22:34, 12 August 2023 edit Teaktl17 (talk | contribs)Extended confirmed users18,074 edits →See also: alt. names |
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{{lowercasetitle}} |
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}} |
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{{chembox |
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{{Chembox |
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| verifiedrevid = 443659318 |
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| verifiedrevid = 477319185 |
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|Name=α-Ketobutyric acid |
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| Name = α-Ketobutyric acid |
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|ImageFile=Alpha-ketobutyric acid.svg |
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| ImageFile = Alpha-ketobutyric acid.svg |
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|ImageSize= |
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| ImageSize = |
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|ImageFile1=Alpha-Ketobutyric acid.png |
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| ImageFile1 = 2-Oxobutanoic acid 3D ball.png |
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| ImageSize1 = |
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|ImageSize= |
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|IUPACName=2-oxobutanoic acid |
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| PIN = 2-Oxobutanoic acid |
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|OtherNames= |
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| OtherNames = |
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|Section1= {{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG = C00109 |
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| KEGG = C00109 |
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| InChI = 1/C4H6O3/c1-2-3(5)4(6)7/h2H2,1H3,(H,6,7) |
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| InChI = 1/C4H6O3/c1-2-3(5)4(6)7/h2H2,1H3,(H,6,7) |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL = 171246 |
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| ChEMBL = 171246 |
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| EINECS = 209-986-9 |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 1S/C4H6O3/c1-2-3(5)4(6)7/h2H2,1H3,(H,6,7) |
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| StdInChI = 1S/C4H6O3/c1-2-3(5)4(6)7/h2H2,1H3,(H,6,7) |
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| StdInChIKey = TYEYBOSBBBHJIV-UHFFFAOYSA-N |
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| StdInChIKey = TYEYBOSBBBHJIV-UHFFFAOYSA-N |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo=600-18-0 |
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| CASNo = 600-18-0 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| PubChem=58 |
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| UNII = B92RB6HY1A |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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⚫ |
| PubChem = 58 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 57 |
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| ChemSpiderID = 57 |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI = 30831 |
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| ChEBI = 30831 |
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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| DrugBank = DB04553 |
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| DrugBank = DB04553 |
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| SMILES = O=C(C(=O)O)CC |
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| SMILES = O=C(C(=O)O)CC |
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| MeSHName=Alpha-ketobutyric+acid |
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| MeSHName = Alpha-ketobutyric+acid |
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}} |
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}} |
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|Section2= {{Chembox Properties |
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|Section2={{Chembox Properties |
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| Formula=C<sub>4</sub>H<sub>6</sub>O<sub>3</sub> |
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| Formula = C<sub>4</sub>H<sub>6</sub>O<sub>3</sub> |
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| MolarMass=102.089 g/mol |
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| MolarMass = 102.089 g/mol |
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| Appearance= |
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| Appearance = colorless solid |
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| Density= |
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| Density = |
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| MeltingPtC = 33 |
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}} |
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}} |
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|Section3= {{Chembox Hazards |
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|Section3={{Chembox Hazards |
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| MainHazards= |
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| FlashPt= |
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}} |
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}} |
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}} |
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}} |
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'''α-Ketobutyric acid''' is an ] with the formula CH<sub>3</sub>CH<sub>2</sub>C(O)CO<sub>2</sub>H. It is a colorless solid that melts just above room temperature. Its conjugate base '''α-ketobutyrate''' is the predominant form found in nature (near neutral pH). It results from the lysis of ]. It is also one of the degradation products of ], produced by the catabolism of the amino acid by ]. It is also produced by the degradation of ] and the metabolism of ]. |
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α-Ketobutyrate is transported into the ], where it is converted to ] by ]. Further mitochondrial reactions produce ]. This is first through the enzyme mitochondria ] with ] as a ] to produce (''S'')-]. This is subsequently converted to (''R'')-methylmalonyl-CoA by mitochondrial ]. Finally, mitochondrial ] with cofactor ] produces succinyl-CoA which enters the ].<ref>http://smpdb.ca/ {{nonspecific|date=August 2022}}</ref> |
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== Conversion in sotolon in French ''vin jaune'' == |
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'']'' is marked by the formation of ] from alpha-ketobutyric acid.<ref>{{ cite journal | vauthors = Pham TT, Guichard E, Schlich P, Charpentier C | title = Optimal Conditions for the Formation of Sotolon from α-Ketobutyric Acid in the French 'Vin Jaune' | journal = Journal of Agricultural and Food Chemistry | year = 1995 | volume = 43 | issue = 10 | pages = 2616–2619 | doi = 10.1021/jf00058a012 }}</ref><ref>{{ cite journal | title = Quantitative Determination of Sotolon in Wines by High-Performance Liquid Chromatography | vauthors = Guichard E, Pham TT, Etievant P | journal = Chromatographia | volume = 37 | issue = 9–10 | pages = 539–542 | doi = 10.1007/BF02275793 | year = 1993 | s2cid = 95494741 }}</ref> |
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== See also == |
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* ] |
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* ] (homoalanine) |
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* ] (α-hydroxybutyric acid) |
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* Other ]s |
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** ] (acetoacetic acid) |
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** ] (succinic semialdehyde) |
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==References== |
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{{reflist}} |
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{{Amino acid metabolism intermediates}} |
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{{DEFAULTSORT:Ketobutyric acid, alpha-}} |
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] |