Canmetcon
Record Information
Version1.0
Creation date2011-04-08 19:48:08 UTC
Update date2015-10-09 22:28:54 UTC
Primary IDFDB021797
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name3-Hydroxybutanoic acid
Description3-Hydroxybutanoic acid is a ketone body. It is a chiral compound having two enantiomers. The concentration of beta-hydroxybutyrate, like that of other ketone bodies, is increased in ketosis. In humans, beta-hydroxybutyrate is synthesized in the liver from acetyl-CoA in a reaction catalyzed by the enzyme beta-hydroxybutyrate dehydrogenase and can be used as an energy source by the brain when blood glucose is low. 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 increasebeta-hydroxybutyrate to oxaloacetate ratio, resulting in TCA cycle stalling and shifting of glucose towards ketone body production. [Wikipedia]
CAS Number300-85-6
Structure
Thumb
Synonyms
SynonymSource
(1)-3-Hydroxybutyric acidChEBI
3 HBAChEBI
3-HydroxybuttersaeureChEBI
3-OH-Butyric acidChEBI
beta-Hydroxy-N-butyric acidChEBI
beta-Hydroxybutanoic acidChEBI
beta-HydroxybuttersaeureChEBI
beta-Hydroxybutyric acidChEBI
BHBAChEBI
DL-beta-Hydroxybutyric acidChEBI
(1)-3-HydroxybutyrateGenerator
3-OH-ButyrateGenerator
b-Hydroxy-N-butyrateGenerator
b-Hydroxy-N-butyric acidGenerator
beta-Hydroxy-N-butyrateGenerator
Β-hydroxy-N-butyrateGenerator
Β-hydroxy-N-butyric acidGenerator
b-HydroxybutanoateGenerator
b-Hydroxybutanoic acidGenerator
beta-HydroxybutanoateGenerator
Β-hydroxybutanoateGenerator
Β-hydroxybutanoic acidGenerator
b-HydroxybuttersaeureGenerator
Β-hydroxybuttersaeureGenerator
b-HydroxybutyrateGenerator
b-Hydroxybutyric acidGenerator
beta-HydroxybutyrateGenerator
Β-hydroxybutyrateGenerator
Β-hydroxybutyric acidGenerator
DL-b-HydroxybutyrateGenerator
DL-b-Hydroxybutyric acidGenerator
DL-beta-HydroxybutyrateGenerator
DL-Β-hydroxybutyrateGenerator
DL-Β-hydroxybutyric acidGenerator
3-HydroxybutyrateGenerator
3-Hydroxy-butanoateHMDB
3-Hydroxy-butanoic acidHMDB
3-Hydroxy-butyrateHMDB
3-Hydroxy-butyric acidHMDB
3-HydroxybutanoateHMDB
3-Hydroxybutanoic acidHMDB
BiopolHMDB
DL-3-HydroxybutyrateHMDB
DL-3-Hydroxybutyric acidHMDB
beta Hydroxybutyric acidHMDB
3 Hydroxybutyric acidHMDB
beta HydroxybutyrateHMDB
(+ -)-3-Hydroxybutyric acidHMDB
3 HydroxybutyrateHMDB
3-Hydroxybutyric acidmanual
DL-β-hydroxybutyrateGenerator
DL-β-hydroxybutyric acidGenerator
β-hydroxy-N-butyrateGenerator
β-hydroxy-N-butyric acidGenerator
β-hydroxybutanoateGenerator
β-hydroxybutanoic acidGenerator
β-hydroxybuttersaeureGenerator
β-hydroxybutyrateGenerator
β-hydroxybutyric acidGenerator
Predicted Properties
PropertyValueSource
Water Solubility539 g/LALOGPS
logP-0.5ALOGPS
logP-0.39ChemAxon
logS0.71ALOGPS
pKa (Strongest Acidic)4.41ChemAxon
pKa (Strongest Basic)-2.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity23.46 m³·mol⁻¹ChemAxon
Polarizability10.01 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC4H8O3
IUPAC name3-hydroxybutanoic acid
InChI IdentifierInChI=1S/C4H8O3/c1-3(5)2-4(6)7/h3,5H,2H2,1H3,(H,6,7)
InChI KeyWHBMMWSBFZVSSR-UHFFFAOYSA-N
Isomeric SMILESCC(O)CC(O)=O
Average Molecular Weight104.1045
Monoisotopic Molecular Weight104.047344122
Classification
Description belongs to the class of organic compounds known as beta hydroxy acids and derivatives. Beta hydroxy acids and derivatives are compounds containing a carboxylic acid substituted with a hydroxyl group on the C3 carbon atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassHydroxy acids and derivatives
Sub ClassBeta hydroxy acids and derivatives
Direct ParentBeta hydroxy acids and derivatives
Alternative Parents
Substituents
  • Short-chain hydroxy acid
  • Beta-hydroxy acid
  • Fatty 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
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)splash10-0002-0900000000-92be5c49a099fe1d9865View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-01ot-1920000000-c93138bf9d35643fef30View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-00dj-8900000000-e632e14fb4be28bdb786View in MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-014l-1900000000-e192caba63f034040624View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0002-0900000000-92be5c49a099fe1d9865View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-01ot-1920000000-c93138bf9d35643fef30View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00dj-8900000000-e632e14fb4be28bdb786View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-014l-1900000000-e192caba63f034040624View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0002-0900000000-d06c5ac1a3733a38ea05View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0007-9000000000-63f261a4dc876e264246View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-01ei-9710000000-2652bd46b41e50defdb0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-0a4i-9200000000-4156904e7472b5e97249View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-0a4i-9300000000-505ae46abb0c49c78b1eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-0zfr-9600000000-dfed69c37c1a4d794440View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-0zfr-4900000000-537084557f5986f16b31View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0zfr-4900000000-537084557f5986f16b31View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT , positivesplash10-000i-9000000000-7f0ec480b3c3c3911acdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kr-9100000000-05c4623b015ff4300a6dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05n0-9000000000-cbe0653845ffe4dc6ad4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-e55d47308c7464e4cb22View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0zfr-8900000000-06dfbf939f6d19983ebeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0pb9-9200000000-48b6e9b8656d41bff9cfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9000000000-f7d61596ff4428fe6b09View in MoNA
MSMass Spectrum (Electron Ionization)splash10-0007-9000000000-7fc414806153ebd8822cView in MoNA
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,1H] 2D NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
ChemSpider ID428
ChEMBL IDCHEMBL1162496
KEGG Compound IDC01089
Pubchem Compound ID441
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB00357
CRC / DFC (Dictionary of Food Compounds) IDGZG28-W:GZG28-W
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDBeta-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
Pathways
NameSMPDB LinkKEGG Link
Fatty Acid BiosynthesisSMP00456 Not Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference