beta-Hydroxybutyric acid
IUPAC name	3-Hydroxybutanoic acid
Identifiers
CAS number	300-85-6 Y
PubChem	441
MeSH	beta-Hydroxybutyrate
SMILES	O=C(O)CC(O)C
InChI	1/C4H8O3/c1-3(5)2-4(6)7/h3,5H,2H2,1H3,(H,6,7)
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
Y (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]

[edit] See also

• Hydroxybutyric acid
• Ketogenesis

[edit] References

v • d • e Cholesterol and steroid metabolic intermediates Mevalonate pathway to HMG-CoA Acetyl-CoA · Acetoacetyl-CoA · HMG-CoA Ketone bodies Acetone · Acetoacetic acid · beta-Hydroxybutyric acid to DMAPP Mevalonic acid · Phosphomevalonic acid · 5-Diphosphomevalonic acid · Isopentenyl pyrophosphate · Dimethylallyl pyrophosphate Geranyl- Geranyl pyrophosphate · Geranylgeranyl pyrophosphate Carotenoid Prephytoene diphosphate · Phytoene Non-mevalonate pathway DOXP · MEP · CDP-ME · CDP-MEP · MEcPP · HMB-PP · IPP · DMAPP To Cholesterol Farnesyl pyrophosphate · Squalene · 2,3-Oxidosqualene · Lanosterol Lanosterol · Lathosterol · 7-Dehydrocholesterol · Cholesterol Lanosterol · Zymosterol · 7-Dehydrodesmosterol · Desmosterol · Cholesterol Steroid Corticosteroids (C21 pregnane) Mineralocorticoids Pregnenolone · Progesterone · 11-Deoxycorticosterone · Corticosterone · Aldosterone Glucocorticoids Pregnenolone · 17-Hydroxypregnenolone · 17-Hydroxyprogesterone · 11-Deoxycortisol · Cortisol Cortisol · Cortisone Sex steroids Androgens (C19 andrane) DHEA · Androstenedione/5-Androstenediol · Testosterone · Dihydrotestosterone DHEA sulfate · Epitestosterone Estrogens (C18 estrane) Estrone · Estradiol · Estriol Nonhuman Phytosterols Stigmasterol · Brassicasterol Ergosterols Ergosterol · Ergocalciferol see also enzymes, disorders Major families of biochemicals Saccharides/Carbohydrates/Glycosides · Amino acids/Peptides/Proteins/Glycoproteins · Lipids/Terpenes/Steroids/Carotenoids · Alkaloids/Nucleobases/Nucleic acids · Cofactors/Phenylpropanoids/Polyketides/Tetrapyrroles