3-Hydroxypentanoic acid

3-Hydroxypentanoic acid is the organic compound with the formula CH3CH2CH(OH)CH2CO2H. It is one of the hydroxypentanoic acids.[1] 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.[2]

3-Hydroxypentanoic acid
Names
Preferred IUPAC name
3-Hydroxypentanoic acid
Other names
3-Hydroxyvalerate
3-Hydroxy valeric acid
beta-Hydroxyvaleric acid
beta-Hydroxypentanoate
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.123.761
UNII
  • InChI=1S/C5H10O3/c1-2-4(6)3-5(7)8/h4,6H,2-3H2,1H3,(H,7,8) checkY
    Key: REKYPYSUBKSCAT-UHFFFAOYSA-N checkY
  • InChI=1/C5H10O3/c1-2-4(6)3-5(7)8/h4,6H,2-3H2,1H3,(H,7,8)
    Key: REKYPYSUBKSCAT-UHFFFAOYAT
  • CCC(CC(=O)O)O
  • O=C(O)CC(O)CC
Properties
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).
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Infobox references

References
  1. Miltenberger, Karlheinz (2000). "Hydroxycarboxylic Acids, Aliphatic". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a13_507.
  2. 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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