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α-Ketoisovaleric acid

α-Ketoisovaleric acid is an organic compound with the formula (CH3)2CHC(O)CO2H. It is a ketoacid. With a melting point just above room temperature, it is usually an oil or semi-solid. The compound is colorless. It is a metabolite of valine and a precursor to pantothenic acid, a prosthetic group found in several cofactors. In the biological context, is usually encountered as its conjugate base ketoisovalerate, (CH3)2CHC(O)CO2.[1]

α-Ketoisovaleric acid
Names
Preferred IUPAC name
3-Methyl-2-oxobutanoic acid
Other names
2-Ketoisovaleric acid; α-Ketovaline
Identifiers
  • 759-05-7 Y
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:16530 Y
ChEMBL
  • ChEMBL146554 Y
ChemSpider
  • 48 Y
DrugBank
  • DB04074 Y
ECHA InfoCard 100.010.969
KEGG
  • C00141 Y
  • 49
UNII
  • 34P71D50E0 Y
  • DTXSID6061078
  • InChI=1S/C5H8O3/c1-3(2)4(6)5(7)8/h3H,1-2H3,(H,7,8) Y
    Key: QHKABHOOEWYVLI-UHFFFAOYSA-N Y
  • InChI=1/C5H8O3/c1-3(2)4(6)5(7)8/h3H,1-2H3,(H,7,8)
    Key: QHKABHOOEWYVLI-UHFFFAOYAY
  • O=C(C(=O)O)C(C)C
Properties
C5H8O3
Molar mass 116.116 g·mol−1
Appearance colorless or white solid or oil
Melting point 31.5 °C (88.7 °F; 304.6 K)
Boiling point 170.5 °C (338.9 °F; 443.6 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y verify (what is YN ?)

Synthesis and reactions edit

α-Ketoisovalerate undergoes hydroxymethylation to give ketopantoate:[1]

(CH3)2CHC(O)CO2 + CH2O → HOCH2(CH3)2CC(O)CO2

This conversion is catalyzed by ketopantoate hydroxymethyltransferase.

Like many α-ketoacids, α-ketoisovaleric acid is prone to decarboxylation to give isobutyraldehyde:

(CH3)2CHC(O)CO2H → (CH3)2CHCHO + CO2

Genetic engineering has been used to produce the biofuel isobutanol by reduction of isobutyraldehyde obtained from ketoisovalerate.[2]

See also edit

References edit

  1. ^ a b Leonardi, Roberta; Jackowski, Suzanne (April 2007). "Biosynthesis of Pantothenic Acid and Coenzyme A". EcoSal Plus. 2 (2). doi:10.1128/ecosalplus.3.6.3.4. ISSN 2324-6200. PMC 4950986. PMID 26443589.
  2. ^ Atsumi, Shota; Hanai, Taizo; Liao, James C. (2008). "Non-Fermentative Pathways for Synthesis of Branched-Chain Higher Alcohols as Biofuels". Nature. 451 (7174): 86–89. Bibcode:2008Natur.451...86A. doi:10.1038/nature06450. PMID 18172501. S2CID 4413113.


ketoisovaleric, acid, organic, compound, with, formula, 2chc, co2h, ketoacid, with, melting, point, just, above, room, temperature, usually, semi, solid, compound, colorless, metabolite, valine, precursor, pantothenic, acid, prosthetic, group, found, several, . a Ketoisovaleric acid is an organic compound with the formula CH3 2CHC O CO2H It is a ketoacid With a melting point just above room temperature it is usually an oil or semi solid The compound is colorless It is a metabolite of valine and a precursor to pantothenic acid a prosthetic group found in several cofactors In the biological context is usually encountered as its conjugate base ketoisovalerate CH3 2CHC O CO2 1 a Ketoisovaleric acid Names Preferred IUPAC name 3 Methyl 2 oxobutanoic acid Other names 2 Ketoisovaleric acid a Ketovaline Identifiers CAS Number 759 05 7 Y 3D model JSmol Interactive image ChEBI CHEBI 16530 Y ChEMBL ChEMBL146554 Y ChemSpider 48 Y DrugBank DB04074 Y ECHA InfoCard 100 010 969 KEGG C00141 Y PubChem CID 49 UNII 34P71D50E0 Y CompTox Dashboard EPA DTXSID6061078 InChI InChI 1S C5H8O3 c1 3 2 4 6 5 7 8 h3H 1 2H3 H 7 8 YKey QHKABHOOEWYVLI UHFFFAOYSA N YInChI 1 C5H8O3 c1 3 2 4 6 5 7 8 h3H 1 2H3 H 7 8 Key QHKABHOOEWYVLI UHFFFAOYAY SMILES O C C O O C C C Properties Chemical formula C 5H 8O 3 Molar mass 116 116 g mol 1 Appearance colorless or white solid or oil Melting point 31 5 C 88 7 F 304 6 K Boiling point 170 5 C 338 9 F 443 6 K Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa Y verify what is Y N Infobox referencesSynthesis and reactions edita Ketoisovalerate undergoes hydroxymethylation to give ketopantoate 1 CH3 2CHC O CO2 CH2O HOCH2 CH3 2CC O CO2 This conversion is catalyzed by ketopantoate hydroxymethyltransferase Like many a ketoacids a ketoisovaleric acid is prone to decarboxylation to give isobutyraldehyde CH3 2CHC O CO2H CH3 2CHCHO CO2 Genetic engineering has been used to produce the biofuel isobutanol by reduction of isobutyraldehyde obtained from ketoisovalerate 2 See also edita Ketovaleric acidReferences edit a b Leonardi Roberta Jackowski Suzanne April 2007 Biosynthesis of Pantothenic Acid and Coenzyme A EcoSal Plus 2 2 doi 10 1128 ecosalplus 3 6 3 4 ISSN 2324 6200 PMC 4950986 PMID 26443589 Atsumi Shota Hanai Taizo Liao James C 2008 Non Fermentative Pathways for Synthesis of Branched Chain Higher Alcohols as Biofuels Nature 451 7174 86 89 Bibcode 2008Natur 451 86A doi 10 1038 nature06450 PMID 18172501 S2CID 4413113 nbsp This biochemistry article is a stub You can help Wikipedia by expanding it vte Retrieved from https en wikipedia org w index php title A Ketoisovaleric acid amp oldid 1173778340, wikipedia, wiki, book, books, library,

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