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beta-Hydroxybutyric acid
Beta-Hydroxybutyric acid-2D-skeletal.svg
IUPAC name
Identifiers
CAS number 300-85-6 Yes check.svgY
PubChem 441
MeSH beta-Hydroxybutyrate
SMILES
InChI
InChI key WHBMMWSBFZVSSR-UHFFFAOYAO
ChemSpider ID 428
Properties
Molecular formula C4H8O3
Molar mass 104.105 g/mol
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
 Yes check.svgY (what is this?)  (verify)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

beta-Hydroxybutyric acid (beta-hydroxybutyrate or 3-hydroxybutyric acid) is a ketone body. It is a chiral compound having two enantiomers, D-3-hydroxybutyric acid and L-3-hydroxybutyric acid. Like the other ketone bodies (acetoacetate and acetone), levels of beta-hydroxybutyrate are raised in ketosis. In humans, beta-hydroxybutyrate is synthesized in the liver from acetyl-CoA, and 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 B-Hydroxybutyrate to oxaloacetate ratio, resulting in TCA cycle stalling and shifting of glucose towards ketone body production

Industrially, it can also be used for the synthesis of biodegradable plastics, such as poly(3-hydroxybutyrate). This polymer can be produced biologically by the bacteria, Alcaligenes eutrophus.[2]

See also

References

  1. ^ O. E. Owen et al. (1967). "Brain Metabolism during Fasting". The Journal of Clinical Investigation 46 (10): 1589–1595. doi:10.1172/JCI105650. PMID 6061736.  
  2. ^ Yoshiharu Doi, Masao Kunioka, Yoshiyuki Nakamura, Kazuo Soga Macromolecules, 1988, 21 (9), 2722–2727, doi=10.1021/ma00187a012.
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