Wikipedia:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and Α-Ketobutyric acid: Difference between pages

{{lowercasetitle}}

{{Chembox

| verifiedrevid = 477319185

| Name = α-Ketobutyric acid

| ImageFile = Alpha-ketobutyric acid.svg

| ImageSize =

| ImageFile1 = 2-Oxobutanoic acid 3D ball.png

| ImageSize1 =

| PIN = 2-Oxobutanoic acid

| OtherNames =

|Section1={{Chembox Identifiers

| KEGG_Ref = {{keggcite|correct|kegg}}

| EINECS = 209-986-9

| CASNo = 600-18-0

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = B92RB6HY1A

| PubChem = 58

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChEBI_Ref = {{ebicite|correct|EBI}}

| MeSHName = Alpha-ketobutyric+acid

}}

|Section2={{Chembox Properties

| Formula = C₄H₆O₃

| MolarMass = 102.089 g/mol

| Appearance = colorless solid

| Density =

| MeltingPtC = 33

| BoilingPt =

| Solubility =

}}

|Section3={{Chembox Hazards

| MainHazards =

| FlashPt =

| AutoignitionPt =

}}

'''α-Ketobutyric acid''' is an [[organic compound]] with the formula CH₃CH₂C(O)CO₂H. 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 [[cystathionine]]. It is also one of the degradation products of [[threonine]], produced by the catabolism of the amino acid by [[threonine dehydratase]]. It is also produced by the degradation of [[homocysteine]] and the metabolism of [[methionine]].

α-Ketobutyrate is transported into the [[mitochondrial matrix]], where it is converted to [[propionyl-CoA]] by [[branched-chain alpha-keto acid dehydrogenase complex]]. Further mitochondrial reactions produce [[succinyl-CoA]]. This is first through the enzyme mitochondria [[propionyl-CoA carboxylase]] with [[biotin]] as a [[cofactor (biochemistry)|cofactor]] to produce (''S'')-[[methylmalonyl-CoA]]. This is subsequently converted to (''R'')-methylmalonyl-CoA by mitochondrial [[methylmalonyl-CoA epimerase]]. Finally, mitochondrial [[methylmalonyl-CoA mutase]] with cofactor [[adenosylcobalamin]] produces succinyl-CoA which enters the [[citric acid cycle]].<ref>http://smpdb.ca/ {{nonspecific|date=August 2022}}</ref>

== Conversion in sotolon in French ''vin jaune'' ==

''[[Vin jaune]]'' is marked by the formation of [[sotolon]] 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>

== See also ==

* [[Butyric acid]]

* [[α-Aminobutyric acid]] (homoalanine)

* [[2-Hydroxybutyric acid]] (α-hydroxybutyric acid)

* Other [[oxobutanoic acid]]s

** [[3-Oxobutanoic acid]] (acetoacetic acid)

** [[4-Oxobutanoic acid]] (succinic semialdehyde)

==References==

{{reflist}}

{{Amino acid metabolism intermediates}}

{{DEFAULTSORT:Ketobutyric acid, alpha-}}

[[Category:Alpha-keto acids]]