2-Hydroxybutyric acid
From Wikipedia, the free encyclopedia
2-Hydroxybutyric acid | |
---|---|
IUPAC name | 2-Hydroxybutanoic acid |
Other names | alpha-hydroxybutyrate |
Identifiers | |
CAS number | [565-70-8] |
PubChem | |
MeSH | |
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.
[edit] References
This article does not cite any references or sources. (February 2008) Please help improve this article by adding citations to reliable sources. Unverifiable material may be challenged and removed. |