2-Hydroxybutyric acid

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ImageFile=2-hydroxybutyric acid.pngImageSize=150px
IUPACName=2-Hydroxybutanoic acid
OtherNames="alpha"-hydroxybutyrate
Section1= Chembox Identifiers
CASNo=565-70-8
PubChem=11266
SMILES=CCC(O)C(=O)O
MeSHName=2-hydroxybutyric+acid
Section2= Chembox Properties
Formula=C₄H₈O₃
MolarMass=104.105
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Section3= Chembox Hazards
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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 (principaly 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 by-product when cystathionine is cleaved to cysteine that is incorporated into glutathione. Chronic shifts in the rate glutathione synthesis may be reflected by urinary excretion of 2-hydroxybutyrate.

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