3-Hydroxypentanoic acid

3-Hydroxypentanoic acid, or beta-hydroxypentanoate 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, 3-hydroxypentanoic acid is anaplerotic, meaning it can refill the pool of TCA cycle intermediates. The triglyceride triheptanoin is used clinically to produce beta-hydroxypentanoate.[1]

3-Hydroxypentanoic acid

Names
IUPAC name 3-Hydroxypentanoic acid
Other names 3-Hydroxyvalerate 3-Hydroxy valeric acid beta-Hydroxyvaleric acid beta-Hydroxypentanoate
Identifiers
CAS Number	10237-77-1^Y
3D model (JSmol)	Interactive image Interactive image
ChemSpider	96952^Y
ECHA InfoCard	100.123.761
PubChem CID	107802
UNII	9D6K40J6UZ^Y
CompTox Dashboard (EPA)	DTXSID00864240
InChI InChI=1S/C5H10O3/c1-2-4(6)3-5(7)8/h4,6H,2-3H2,1H3,(H,7,8)^Y Key: REKYPYSUBKSCAT-UHFFFAOYSA-N^Y InChI=1/C5H10O3/c1-2-4(6)3-5(7)8/h4,6H,2-3H2,1H3,(H,7,8) Key: REKYPYSUBKSCAT-UHFFFAOYAT
SMILES CCC(CC(=O)O)O O=C(O)CC(O)CC
Properties
Chemical formula	C5H10O3
Molar mass	118.13 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

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