3-Oxopentanoic acid

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.

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	10191-25-0 Y
3D model (JSmol)	Interactive image Interactive image
ChEBI	CHEBI:27401 Y
ChemSpider	388751 Y
KEGG	C02233 Y
PubChem CID	439684
UNII	090PW368EP Y
CompTox Dashboard (EPA)	DTXSID50331432
InChI InChI=1S/C5H8O3/c1-2-4(6)3-5(7)8/h2-3H2,1H3,(H,7,8) Y Key: FHSUFDYFOHSYHI-UHFFFAOYSA-N Y 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 [77 °F], 100 kPa). N verify (what is YN ?) Infobox references

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.^[1]

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