Record Information
Version1.0
Creation date2011-09-21 00:04:15 UTC
Update date2018-05-29 01:52:41 UTC
Primary IDFDB021869
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name(R)-3-Hydroxybutyric acid
Description(R)-3-Hydroxybutyric acid is a butyric acid substituted with a hydroxyl group in the beta or 3 position. It is involved in the synthesis and degradation of ketone bodies. Like the other ketone bodies (acetoacetate and acetone), levels of beta-hydroxybutyrate are raised in the blood and urine in ketosis. Beta-hydroxybutyrate is a typical partial-degradation product of branched-chain amino acids (primarily valine) released from muscle for hepatic and renal gluconeogenesis This acid is metabolized by 3-hydroxybutyrate dehydrogenase (catalyzes the oxidation of D-3-hydroxybutyrate to form acetoacetate, using NAD+ as an electron acceptor). The enzyme functions in nervous tissues and muscles, enabling the use of circulating hydroxybutyrate as a fuel. In the liver mitochondrial matrix, the enzyme can also catalyze the reverse reaction, a step in ketogenesis. 3-Hydroxybutyric acid is a chiral compound having two enantiomers, D-3-hydroxybutyric acid and L-3-hydroxybutyric acid. 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. It can also be used for the synthesis of biodegradable plastics . [HMDB]
CAS Number625-72-9
Structure
Thumb
Synonyms
SynonymSource
(R)-(-)-b-Hydroxybutyratehmdb
(R)-(-)-b-Hydroxybutyric acidhmdb
(R)-(-)-beta-Hydroxybutyratehmdb
(R)-(-)-beta-Hydroxybutyric acidhmdb
(R)-(-)-β-hydroxybutyrateGenerator
(R)-(-)-β-hydroxybutyric acidGenerator
(R)-3-Hydroxybutanoatehmdb
(R)-3-Hydroxybutanoic acidhmdb
(R)-3-Hydroxybutyratehmdb
3-D-hydroxybutyratehmdb
3-D-hydroxybutyric acidhmdb
3-delta-hydroxybutyratehmdb
3-delta-hydroxybutyric acidhmdb
BHIBhmdb
D-(-)-3-hydroxybutyratehmdb
D-3-hydroxybutyratehmdb
D-3-hydroxybutyric acidhmdb
D-beta-hydroxybutyratehmdb
delta-(-)-3-hydroxybutyratehmdb
delta-3-hydroxybutyratehmdb
delta-3-hydroxybutyric acidhmdb
delta-beta-hydroxybutyratehmdb
Predicted PropertiesNot Available
Chemical FormulaC4H8O3
IUPAC name
InChI IdentifierInChI=1S/C4H8O3/c1-3(5)2-4(6)7/h3,5H,2H2,1H3,(H,6,7)/t3-/m1/s1
InChI KeyWHBMMWSBFZVSSR-GSVOUGTGSA-N
Isomeric SMILESC[C@@H](O)CC(O)=O
Average Molecular Weight104.1045
Monoisotopic Molecular Weight104.047344122
Classification
ClassificationNot classified
Ontology
Physiological effect

Health effect:

Disposition

Source:

Biological location:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MSNot Available
MS/MSNot Available
NMRNot Available
ChemSpider ID83181
ChEMBL IDCHEMBL1162484
KEGG Compound IDC01089
Pubchem Compound ID92135
Pubchem Substance IDNot Available
ChEBI ID17066
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB00011
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID36784
KNApSAcK IDNot Available
HET ID3HR
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
Novel protein similar to 3-hydroxymethyl-3-methylglutaryl-Coenzyme A lyase (Hydroxymethylglutaricaciduria)DKFZp434G1411Q9NT06
Pathways
NameSMPDB LinkKEGG Link
Ketone Body MetabolismSMP00071 map00072
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference