beta-Hydroxybutyric acid

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beta-Hydroxybutyric acid
Beta-Hydroxybutyric acid-2D-skeletal.svg
Identifiers
CAS number 300-85-6 YesY
PubChem 441
ChemSpider 428 YesY
MeSH beta-Hydroxybutyrate
ChEBI CHEBI:20067 YesY
ChEMBL CHEMBL1162496 YesY
IUPHAR ligand 1593
Jmol-3D images Image 1
Image 2
Properties
Molecular formula C4H8O3
Molar mass 104.10 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
butyric acid
hydroxypentanoic acid
Related compounds erythrose
threose
1,2-butanediol
1,3-butanediol
2,3-butanediol
1,4-butanediol
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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Infobox references

beta-Hydroxybutyric acid (also known as beta-hydroxybutyrate, 3-hydroxybutyric acid or 3-hydroxybutyrate) is an organic compound with the formula CH3CH(OH)CH2CO2H. It is a beta hydroxy acid. It is a chiral compound having two enantiomers, D-3-hydroxybutyric acid and L-3-hydroxybutyric acid. Its oxidized and polymeric derivatives occur widely in nature.

Biosynthesis[edit]

In humans, beta-hydroxybutyrate is synthesized in the liver from acetyl-CoA. The biosynthesis is catalyzed by the enzyme beta-hydroxybutyrate dehydrogenase.

The concentration of beta-hydroxybutyrate, like that of other ketone bodies, is raised in ketosis. The compound can be used as an energy source by the brain when blood glucose is low.[1] Diabetic patients can have their ketone levels tested via urine or blood to indicate diabetic ketoacidosis. In alcoholic ketoacidosis, this ketone body is produced in greatest concentration. Both types of ketoacidosis result in an increase beta-hydroxybutyrate to oxaloacetate ratio, resulting in TCA cycle stalling and shifting of glucose towards ketone body production.[clarification needed]

Laboratory and industrial chemistry[edit]

beta-Hydroxybutyric acid is the precursor to polyesters, which are biodegradable plastics. Known as poly(3-hydroxybutyrate), this polymer is also produced biologically by the bacteria Alcaligenes eutrophus.[2]

beta-Hydroxybutyrate can be extracted from poly(3-hydroxybutyrate) by acid hydrolysis.[3]

See also[edit]

References[edit]

  1. ^ O. E. Owen et al. (1967). "Brain Metabolism during Fasting". The Journal of Clinical Investigation 46 (10): 1589–1595. doi:10.1172/JCI105650. PMC 292907. PMID 6061736. 
  2. ^ Yoshiharu Doi, Masao Kunioka, Yoshiyuki Nakamura, Kazuo Soga (1988). "Nuclear magnetic resonance studies on unusual bacterial copolyesters of 3-hydroxybutyrate and 4-hydroxybutyrate". Macromolecules 21 (9): 2722–2727. doi:10.1021/ma00187a012. 
  3. ^ Dieter Seebach, Albert K. Beck, Richard Breitschuh, and Kurt Job "Direct Degradation of the Biopolymer Poly[(R)-3-Hydroxybutrric Acid to (R)-3-Hydroxybutanoic Acid and Its Methyl Ester" Org. Synth. 1993, 71, 39. doi:10.15227/orgsyn.071.0039