beta-Hydroxybutyric acid

beta-Hydroxybutyric acid
beta-Hydroxybutyric acid
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 104.1 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
 YesY acid (verify) (what is: YesY/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

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. 

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  • Beta-Hydroxybutyric acid — Chembox new ImageFile = Beta hydroxybutyrate.png ImageSize = IUPACName = 3 Hydroxybutyric acid OtherNames = Section1 = Chembox Identifiers CASNo = 300 85 6 PubChem = 441 ChemSpiderID = 428 SMILES = CC(O)CC(=O)O MeSHName = beta Hydroxybutyrate… …   Wikipedia

  • beta-hydroxybutyric acid — noun beta derivative of hydroxybutyric acid that is found in the blood and urine in some cases of impaired metabolism • Hypernyms: ↑ketone body, ↑acetone body, ↑hydroxybutyric acid, ↑oxybutyric acid …   Useful english dictionary

  • beta-hydroxybutyric acid — /ˌbitə haɪdrɒksibjuˌtɪrɪk ˈæsəd/ (say .beetuh huydrokseebyooh.tirik asuhd) noun a carboxylic acid, CH3 CHOH CH2 COOH, distributed widely in nature; it is one of the ketone bodies and is an intermediate in fatty acid synthesis and breakdown …  

  • Gamma-amino-beta-hydroxybutyric acid — drugbox IUPAC name = 4 amino 3 hydroxybutanoic acid width = 200 width = 180 CAS number = 352 21 6 ChemSpiderID = 2064 ATC prefix = ATC suffix = PubChem = 2149 DrugBank = C=4|H=9|N=1|O=3 molecular weight = 119.12 g/mol bioavailability = protein… …   Wikipedia

  • Beta hydroxy acid — A beta hydroxy acid (BHA) is an organic compound which contains a carboxylic acid functional group and hydroxy functional group separated by two carbon atoms. They are closely related to alpha hydroxy acids, in which the two functional groups are …   Wikipedia

  • Hydroxybutyric acid — is a group of four carbon organic compounds that have both hydroxyl and carboxylic acid functional groups. They can be viewed as derivatives of butyric acid. The carboxylate anion and the esters of hydroxybutyric acids are known as… …   Wikipedia

  • hydroxybutyric acid — noun hydroxy derivative of butyric acid • Syn: ↑oxybutyric acid • Hypernyms: ↑butyric acid, ↑butanoic acid • Hyponyms: ↑beta hydroxybutyric acid * * * “+... noun …   Useful english dictionary

  • hydroxybutyric acid — [hī dräks΄ē byo͞o tir′ik, hīdräks΄ibyo͞o tir′ik] n. any of three isomeric acids, CH3CH(OH)CH2COOH: the beta isomer is found in the urine of diabetics …   English World dictionary

  • Gamma-Hydroxybutyric acid — γ Hydroxybutyric acid Systematic (IUPAC) name 4 Hydroxybutanoic acid …   Wikipedia

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