Record Information
Version1.0
Creation date2015-10-09 22:31:06 UTC
Update date2017-01-19 02:36:26 UTC
FoodComEx IDPC000512
FoodDB RecordFDB021867
Chemical Information
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
Chemical FormulaC4H8O3
IUPAC name2-hydroxybutanoic acid
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
Chemical Taxonomy
Description Belongs to the class of organic compounds known as alpha hydroxy acids and derivatives. These are organic compounds containing a carboxylic acid substituted with a hydroxyl group on the adjacent carbon.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassHydroxy acids and derivatives
Sub ClassAlpha hydroxy acids and derivatives
Direct ParentAlpha hydroxy acids and derivatives
Alternative Parents
Substituents
  • Fatty acid
  • Alpha-hydroxy acid
  • Secondary alcohol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physico-Chemical Properties - Experimental
PropertyValueReference
Experimental logPNot Available
Experimental Water SolubilityNot Available
Melting PointNot Available
Foods of Origin
FoodContent Range AverageReference
FoodReference
Production Data
Production Methodcommercial
Production Method ReferenceNot Available
Production Method Reference FileNot Available
Quantity AvailableProduction upon request, up to 10 mg
Delivery TimeNot Available
Storage Formsolid
Storage Conditions-80°C
StabilityNot Available
PurityNot Available
Spectra
Spectral Data Upon RequestNot Available
Provider Information
Contact NameContact InstitutionContact Email
Rosa Vazquez Fresnovazquezf@ualberta.ca
Commercial Vendors
AKSci Z2570
MetaSci HMDB0000008
Sigma-Aldrich HMDB0000008
Toronto Research Chemicals H831185