2-Hydroxybutyric acid

2-Hydroxybutyric acid, is a hydroxybutyric acid with the hydroxyl group on the carbon adjacent to the carboxyl. It is a chiral compound having two enantiomers, D-2-hydroxybutyric acid and L-2-hydroxybutyric acid. Its conjugate base is known as alpha-hydroxybutyrate and α-hydroxybutyrate.

  • d-2-hydroxybutyric acid
  • l-2-hydroxybutyric acid
2-Hydroxybutyric acid
Names
Preferred IUPAC name
2-Hydroxybutanoic acid
Other names
α-Hydroxybutyric acid
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.009.079
KEGG
MeSH 2-hydroxybutyric+acid
PubChem CID
UNII
  • InChI=1S/C4H8O3/c1-2-3(5)4(6)7/h3,5H,2H2,1H3,(H,6,7) Y
    Key: AFENDNXGAFYKQO-UHFFFAOYSA-N Y
  • InChI=1/C4H8O3/c1-2-3(5)4(6)7/h3,5H,2H2,1H3,(H,6,7)
    Key: AFENDNXGAFYKQO-UHFFFAOYAH
SMILES
  • CCC(O)C(=O)O
  • O=C(O)C(O)CC
Properties
C4H8O3
Molar mass 104.105 g·mol−1
Related compounds
Other anions
 hydroxybutyrate
propionic acid
lactic acid
3-hydroxypropionic acid
malonic acid
butyric acid
hydroxypentanoic acid
Related compounds
 erythrose
threose
1,2-butanediol
1,3-butanediol
2,3-butanediol
1,4-butanediol
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

2-Hydroxybutyrate, the conjugate base of 2-hydroxybutyric acid, is produced in mammalian tissues (principally hepatic) that catabolize L-threonine or synthesize glutathione. Oxidative stress or detoxification demands can dramatically increase the rate of hepatic glutathione synthesis. Under such metabolic stress conditions, supplies of L-cysteine for glutathione synthesis become limiting, so homocysteine is diverted from the transmethylation pathway forming methionine into the transsulfuration pathway forming cystathionine. 2-Hydroxybutyrate is released as a byproduct when cystathionine is cleaved to cysteine that is incorporated into glutathione. Chronic shifts in the rate of glutathione synthesis may be reflected by urinary excretion of 2-hydroxybutyrate.

α-hydroxybutyrate may be useful as an early indicator of insulin resistance in non-diabetic subjects. Moreover, elevated serum α-hydroxybutyrate predicts worsening glucose tolerance.

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