2-Hydroxybutyric acid

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2-Hydroxybutyric acid
2-hydroxybutyric acid.png
2-Hydroxybutyric acid molecule
Identifiers
CAS number 565-70-8
PubChem 11266
ChemSpider 10792 YesY
MeSH 2-hydroxybutyric+acid
ChEBI CHEBI:1148 YesY
ChEMBL CHEMBL567588 YesY
Jmol-3D images Image 1
Image 2
Properties
Molecular formula C4H8O3
Molar mass 104.10 g mol−1
Related compounds
Other anions hydroxybutyrate
Related carboxylic acids 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 noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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Infobox references

2-Hydroxybutyric acid (or alpha-hydroxybutyrate) 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.

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.

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