Record Information
Version1.0
Creation date2011-09-21 00:04:13 UTC
Update date2019-11-26 03:21:00 UTC
Primary IDFDB021867
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name2-Hydroxybutyric acid
Description2-Hydroxybutyric acid is an organic acid that is involved in propanoate metabolism. It is produced in mammalian tissues (principaly hepatic) that catabolize L-threonine or synthesize glutathione. Oxidative stress or detoxification demands can dramatically increase the rate of hepatic glutathione synthesis. Under such metabolic stress conditions, supplies of L-cysteine for glutathione synthesis become limiting, so homocysteine is diverted from the transmethylation pathway forming methionine into the transsulfuration pathway forming cystathionine. 2-Hydroxybutyrate is released as a by-product when cystathionine is cleaved to cysteine that is incorporated into glutathione. 2-Hydroxybutyric acid is often found in the urine of patients suffering from lactic acidosis and ketoacidosis. 2-Hydroxybutyric acid generally appears at high concentrations in situations related to deficient energy metabolism (e.g., birth asphyxia) and also in inherited metabolic diseases affecting the central nervous system during neonatal development, such as "cerebral" lactic acidosis, glutaric aciduria type II, dihydrolipoyl dehydrogenase (E3) deficiency, and propionic acidemia. More recently it has been noted that elevated levels of alpha-hydroxybutyrate in the plasma is a good marker for early stage type II diabetes (PMID: 19166731). It was concluded from studies done in the mid 1970's that an increased NADH2/NAD ratio was the most important factor for the production of 2-hydorxybutyric acid (PMID: 168632) [HMDB]
CAS Number600-15-7
Structure
Thumb
Synonyms
SynonymSource
(RS)-2-Hydroxybutyratehmdb
(RS)-2-Hydroxybutyric acidhmdb
2-hydroxy-Butanoatehmdb
2-hydroxy-Butanoic acidhmdb
2-hydroxy-DL-Butyratehmdb
2-hydroxy-DL-Butyric acidhmdb
2-Hydroxy-n-butyratehmdb
2-Hydroxy-n-butyric acidhmdb
2-Hydroxybutanoatehmdb
2-Hydroxybutanoic acidhmdb
2-Hydroxybutyratehmdb
a-Hydroxy-n-butyratehmdb
a-Hydroxy-n-butyric acidhmdb
a-Hydroxybutanoatehmdb
a-Hydroxybutanoic acidhmdb
a-Hydroxybutyratehmdb
a-Hydroxybutyric acidhmdb
alpha-hydroxy-n-butyratehmdb
alpha-hydroxy-n-butyric acidhmdb
alpha-Hydroxybutanoatehmdb
alpha-Hydroxybutanoic acidhmdb
alpha-Hydroxybutyratehmdb
alpha-Hydroxybutyric acidhmdb
DL-2-Hydroxybutanoatehmdb
DL-2-Hydroxybutanoic acidhmdb
DL-a-Hydroxybutyratehmdb
DL-a-Hydroxybutyric acidhmdb
DL-alpha-Hydroxybutyratehmdb
DL-alpha-Hydroxybutyric acidhmdb
α-hydroxybutanoateGenerator
α-hydroxybutanoic acidGenerator
α-hydroxybutyrateGenerator
α-hydroxybutyric acidGenerator
Predicted PropertiesNot Available
Chemical FormulaC4H8O3
IUPAC name
InChI IdentifierInChI=1S/C4H8O3/c1-2-3(5)4(6)7/h3,5H,2H2,1H3,(H,6,7)
InChI KeyAFENDNXGAFYKQO-UHFFFAOYSA-N
Isomeric SMILESCCC(O)C(O)=O
Average Molecular Weight104.1045
Monoisotopic Molecular Weight104.047344122
Classification
ClassificationNot classified
Ontology
Physiological effect

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Disposition

Source:

Biological location:

Role

Biological role:

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 ID10792
ChEMBL IDCHEMBL567588
KEGG Compound IDC05984
Pubchem Compound ID11266
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB00008
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID47130
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia ID2-Hydroxybutyric acid
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
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference