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2-Hydroxybutyric acid IUPAC name 2-Hydroxybutanoic acid Other names alpha-hydroxybutyrate Identifiers CAS number 565-70-8 PubChem 11266 ChemSpider 10792 Y MeSH 2-hydroxybutyric+acid ChEMBL CHEMBL567588 Y SMILES CCC(O)C(=O)O O=C(O)C(O)CC InChI 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 Properties Molecular formula C4H8O3 Molar mass 104.1 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  Y(what is this?)  (verify) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) 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. References This article does not cite any references or sources. Please help improve this article by adding citations to reliable sources. Unsourced material may be challenged and removed. (February 2008) This biochemistry article is a stub. You can help Wikipedia by expanding it.v · d · e