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3-Oxopentanoic acid

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(Redirected from Beta-ketopentanoate)
3-Oxopentanoic acid
Names
Preferred IUPAC name 3-Oxopentanoic acid
Other names β-Ketopentanoate
3-Oxopentanoate
3-Oxovaleric acid
3-Ketovaleric acid
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChemSpider
KEGG
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C5H8O3/c1-2-4(6)3-5(7)8/h2-3H2,1H3,(H,7,8)Key: FHSUFDYFOHSYHI-UHFFFAOYSA-N
  • InChI=1/C5H8O3/c1-2-4(6)3-5(7)8/h2-3H2,1H3,(H,7,8)Key: FHSUFDYFOHSYHI-UHFFFAOYAQ
SMILES
  • CCC(=O)CC(=O)O
  • O=C(CC)CC(=O)O
Properties
Chemical formula C5H8O3
Molar mass 116.12 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

3-Oxopentanoic acid, or beta-ketopentanoate, is a 5-carbon ketone body. It is made from odd carbon fatty acids in the liver and rapidly enters the brain.

As opposed to 4-carbon ketone bodies, beta-ketopentanoate is anaplerotic, meaning it can refill the pool of TCA cycle intermediates. The triglyceride triheptanoin is used clinically to produce beta-ketopentanoate.

References

  1. Renée P. Kinman; Takhar Kasumov; Kathryn A. Jobbins; Katherine R. Thomas; Jillian Adams; Lisa N. Brunengraber; Gerd Kutz; Wolf-Ulrich Brewer; Charles R. Roe & Henri Brunengraber (2006). "Parenteral and Enteral Metabolism of Anaplerotic Triheptanoin in Normal Rats". Am J Physiol Endocrinol Metab. 291 (4): E860 – E866. doi:10.1152/ajpendo.00366.2005. PMID 16705058. Reprint
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