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3-Hydroxyvaleric acid

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3-Hydroxyvaleric acid
Names
Preferred IUPAC name 3-Hydroxypentanoic acid
Other names β-Hydroxyvaleric acid
β-Hydroxypentanoic acid
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.123.761 Edit this at Wikidata
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C5H10O3/c1-2-4(6)3-5(7)8/h4,6H,2-3H2,1H3,(H,7,8)Key: REKYPYSUBKSCAT-UHFFFAOYSA-N
  • 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 118.132 g·mol
Solubility in water 784.8 g/L (estimated)
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-Hydroxyvaleric acid (3-hydroxypentanoic acid) is the organic compound with the formula CH3CH2CH(OH)CH2CO2H. It is one of the hydroxypentanoic acids. It is made from odd carbon fatty acids in the liver and rapidly enters the brain. As opposed to 4-carbon ketone bodies, 3-hydroxyvaleric acid is anaplerotic, meaning it can refill the pool of TCA cycle intermediates. The triglyceride triheptanoin is used clinically to produce 3-hydroxyvalerate (the carboxylate form).

Properties

  • Solubility in water: 784.8 g/L at 25 °C (estimated)

References

  1. Miltenberger, Karlheinz (2000). "Hydroxycarboxylic Acids, Aliphatic". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a13_507. ISBN 3527306730.
  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" (PDF). Am J Physiol Endocrinol Metab. 291 (4): E860–E866. doi:10.1152/ajpendo.00366.2005. PMID 16705058.
  3. "Human Metabolome Database: Showing metabocard for 3-Hydroxyvaleric acid (HMDB0000531)".
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