β-Hydroxybutyric acid
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β-Hydroxybutyric acid, also known as 3-hydroxybutyric acid or BHB, is an organic compound and a beta hydroxy acid with the chemical formula CH3CH(OH)CH2CO2H; its conjugate base is β-hydroxybutyrate, also known as 3-hydroxybutyrate. β-Hydroxybutyric acid is a chiral compound with two enantiomers: D-β-hydroxybutyric acid and L-β-hydroxybutyric acid. Its oxidized and polymeric derivatives occur widely in nature. In humans, D-β-hydroxybutyric acid is one of two primary endogenous agonists of hydroxycarboxylic acid receptor 2 (HCA2), a Gi/o-coupled G protein-coupled receptor (GPCR).[1][2]
Not to be confused with β-Hydroxy β-methylbutyric acid.
Quick Facts Names, Identifiers ...
Names | |
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Preferred IUPAC name
3-Hydroxybutanoic acid | |
Identifiers | |
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3D model (JSmol) |
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3DMet | |
773861 | |
ChEBI | |
ChEMBL | |
ChemSpider |
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ECHA InfoCard | 100.005.546 |
KEGG | |
MeSH | beta-Hydroxybutyrate |
PubChem CID |
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UNII | |
CompTox Dashboard (EPA) |
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Properties | |
C4H8O3 | |
Molar mass | 104.105 g·mol−1 |
Appearance | white solid |
Melting point | 44-46 |
Related compounds | |
Other anions |
hydroxybutyrate |
Related carboxylic acids |
propionic acid lactic acid 3-hydroxypropanoic acid malonic acid hydroxypentanoic acid butyric acid β-methylbutyric acid β-hydroxy β-methylbutyric acid |
Related compounds |
erythrose threose 1,2-butanediol 1,3-butanediol 2,3-butanediol 1,4-butanediol |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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