| beta-Hydroxybutyric acid | |
|---|---|
 |
|
| IUPAC name |
3-Hydroxybutanoic acid
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| Identifiers | |
| CAS number | 300-85-6  |
| PubChem | 441 |
| MeSH | beta-Hydroxybutyrate |
| SMILES |
O=C(O)CC(O)C
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| InChI |
1/C4H8O3/c1-3(5)2-4(6)7/h3,5H,2H2,1H3,(H,6,7)
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| 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 |
| (what is this?) (verify) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
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| 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
- ^ O. E. Owen et al. (1967). "Brain Metabolism during Fasting". The Journal of Clinical Investigation 46 (10): 1589–1595. doi:. PMID 6061736.
- ^ Yoshiharu Doi, Masao Kunioka, Yoshiyuki Nakamura, Kazuo Soga Macromolecules, 1988, 21 (9), 2722–2727, doi=10.1021/ma00187a012.
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