Record Information
Version1.0
Creation date2011-09-21 00:04:13 UTC
Update date2019-11-27 17:42:25 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
2-Hydroxybutanoic acidChEBI
alpha-Hydroxybutanoic acidChEBI
alpha-Hydroxybutyric acidChEBI
2-HydroxybutanoateGenerator
a-HydroxybutanoateGenerator
a-Hydroxybutanoic acidGenerator
alpha-HydroxybutanoateGenerator
Α-hydroxybutanoateGenerator
Α-hydroxybutanoic acidGenerator
a-HydroxybutyrateGenerator
a-Hydroxybutyric acidGenerator
alpha-HydroxybutyrateGenerator
Α-hydroxybutyrateGenerator
Α-hydroxybutyric acidGenerator
2-HydroxybutyrateGenerator
(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
a-Hydroxy-N-butyrateHMDB
a-Hydroxy-N-butyric acidHMDB
alpha-Hydroxy-N-butyrateHMDB
alpha-Hydroxy-N-butyric acidHMDB
DL-2-HydroxybutanoateHMDB
DL-2-Hydroxybutanoic acidHMDB
DL-a-HydroxybutyrateHMDB
DL-a-Hydroxybutyric acidHMDB
DL-alpha-HydroxybutyrateHMDB
DL-alpha-Hydroxybutyric acidHMDB
2-Hydroxybutyric acid, (R)-isomerHMDB
2-Hydroxybutyric acid, monosodium saltHMDB
2-Hydroxybutyric acid, (+-)-isomerHMDB
2-Hydroxybutyric acid, monosodium salt, (+-)-isomerHMDB
(+/-)a-hydoxy butyrateHMDB
(+/-)a-hydoxy butyric acidHMDB
(+/-)alpha-hydoxy butyrateHMDB
(+/-)α-hydoxy butyrateHMDB
(+/-)α-hydoxy butyric acidHMDB
2-Hydroxybutyric acidMeSH
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
a-Hydroxy-n-butyratehmdb
a-Hydroxy-n-butyric acidhmdb
alpha-hydroxy-n-butyratehmdb
alpha-hydroxy-n-butyric acidhmdb
α-hydroxybutanoateGenerator
α-hydroxybutanoic acidGenerator
α-hydroxybutyrateGenerator
α-hydroxybutyric acidGenerator
Predicted Properties
PropertyValueSource
Water Solubility484 g/LALOGPS
logP-0.16ALOGPS
logP0.051ChemAxon
logS0.67ALOGPS
pKa (Strongest Acidic)3.99ChemAxon
pKa (Strongest Basic)-3.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity23.36 m³·mol⁻¹ChemAxon
Polarizability9.98 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
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
Classification
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
Ontology
Physiological effect

Health effect:

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
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-001j-0900000000-44dd1bf8072e5731bac4View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-00e9-9700000000-93eba027d5343e3d6ce1View in MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-001i-1910000000-3bc9898b26df33cad244View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-9000000000-4d935da8e593ec61fd96View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-001j-0900000000-44dd1bf8072e5731bac4View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00e9-9700000000-93eba027d5343e3d6ce1View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-001i-1910000000-3bc9898b26df33cad244View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a6u-9000000000-0d95c1179b1b00650601View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00v0-9520000000-598a2bd61c303327bd8fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-0zfr-9600000000-f688c3e6fdeb5f0270c5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-0a4j-9200000000-e3b371c29b9ebed3199bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-0zfs-9700000000-bccfada2c97e04d34417View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positivesplash10-0a4i-9000000000-4d935da8e593ec61fd96View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT , negativesplash10-0udi-2900000000-3c7915ea71886873f024View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-0zfr-7900000000-d91c840306a06d4ea513View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-9500000000-8f04a5941997004743d2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-9100000000-cef703dc6f30af7834a8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9000000000-1e7e6e8a895c4c1d51dbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-4900000000-d0907a0b08e0d829cecaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0pb9-9200000000-d826b54f814ac185b4dbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9000000000-3727124ed618f038b514View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
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