beta-Hydroxybutyric acid

beta-Hydroxybutyric acid
IUPAC name 3-Hydroxybutanoic acid
Identifiers
CAS number	300-85-6 Y
PubChem	441
ChemSpider	428 Y
MeSH	beta-Hydroxybutyrate
ChEBI	CHEBI:20067 Y
ChEMBL	CHEMBL1162496 Y
IUPHAR ligand	1593
Jmol-3D images	Image 1 Image 2
SMILES O=C(O)CC(O)C CC(CC(=O)O)O
InChI InChI=1S/C4H8O3/c1-3(5)2-4(6)7/h3,5H,2H2,1H3,(H,6,7) Y Key: WHBMMWSBFZVSSR-UHFFFAOYSA-N Y InChI=1/C4H8O3/c1-3(5)2-4(6)7/h3,5H,2H2,1H3,(H,6,7) Key: WHBMMWSBFZVSSR-UHFFFAOYAO
Properties
Molecular formula	C4H8O3
Molar mass	104.1 g mol−1
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
Y acid (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

beta-Hydroxybutyric acid (also known as 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.

In industry, 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

• Hydroxybutyric acid
• Ketogenesis

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. PMC 292907. PMID 6061736. http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=292907. 
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.