2-Hydroxybutyric acid

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2-Hydroxybutyric acid
IUPAC name	2-Hydroxybutanoic acid
Other names	alpha-hydroxybutyrate
Identifiers
CAS number	[565-70-8]
PubChem	11266
MeSH	2-hydroxybutyric+acid
SMILES	CCC(O)C(=O)O
Properties
Molecular formula	C4H8O3
Molar mass	104.105
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and 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 (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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