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Record Information
Version1.0
Creation Date2016-09-30 22:07:18 UTC
Update Date2019-02-05 20:35:41 UTC
MCDB ID BMDB00008
Secondary Accession NumbersNone
Metabolite Identification
Common Name2-Hydroxybutyric acid
Description2-Hydroxybutyric acid, also known as alpha-hydroxybutyrate or 2-hydroxybutanoate, 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. 2-Hydroxybutyric acid exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. 2-Hydroxybutyric acid exists in all living species, ranging from bacteria to humans. 2-Hydroxybutyric acid is a potentially toxic compound.
Structure
Thumb
Synonyms
ValueSource
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
Chemical FormulaC4H8O3
Average Molecular Weight104.1045
Monoisotopic Molecular Weight104.047344122
IUPAC Name2-hydroxybutanoic acid
Traditional Nameα-hydroxybutyric acid
CAS Registry Number600-15-7
SMILES
CCC(O)C(O)=O
InChI Identifier
InChI=1S/C4H8O3/c1-2-3(5)4(6)7/h3,5H,2H2,1H3,(H,6,7)
InChI KeyAFENDNXGAFYKQO-UHFFFAOYSA-N
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
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point44.2 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-001j-0900000000-44dd1bf8072e5731bac4JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-00e9-9700000000-93eba027d5343e3d6ce1JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-001i-1910000000-3bc9898b26df33cad244JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-9000000000-4d935da8e593ec61fd96JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-001j-0900000000-44dd1bf8072e5731bac4JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00e9-9700000000-93eba027d5343e3d6ce1JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-001i-1910000000-3bc9898b26df33cad244JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a6u-9000000000-0d95c1179b1b00650601JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00v0-9520000000-598a2bd61c303327bd8fJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-0zfr-9600000000-f688c3e6fdeb5f0270c5JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-0a4j-9200000000-e3b371c29b9ebed3199bJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-0zfs-9700000000-bccfada2c97e04d34417JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positivesplash10-0a4i-9000000000-4d935da8e593ec61fd96JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT , negativesplash10-0udi-2900000000-3c7915ea71886873f024JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-0zfr-7900000000-d91c840306a06d4ea513JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-9500000000-8f04a5941997004743d2JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-9100000000-cef703dc6f30af7834a8JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9000000000-1e7e6e8a895c4c1d51dbJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-4900000000-d0907a0b08e0d829cecaJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0pb9-9200000000-d826b54f814ac185b4dbJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9000000000-3727124ed618f038b514JSpectraViewer | MoNA
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
Concentrations
StatusValueReferenceDetails
Detected but not QuantifiedNot Applicable details
Detected but not QuantifiedNot Applicable details
HMDB IDHMDB0000008
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB021867
KNApSAcK IDNot Available
Chemspider ID10792
KEGG Compound IDC05984
BioCyc IDNot Available
BiGG ID47130
Wikipedia Link2-Hydroxybutyric_acid
METLIN ID3783
PubChem Compound11266
PDB IDNot Available
ChEBI ID1148
References
Synthesis ReferenceCarlier, J. P.; Henry, C.; Lorin, V.; Rouffignat, K. Conversion of DL-threonine, D-threonine and 2-oxobutyrate into propionate and 2-hydroxybutyrate by Fusobacterium species. Letters in Applied Microbiology (1997), 25(5), 371-374.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743. [PubMed:23438684 ]
  2. Sun HZ, Shi K, Wu XH, Xue MY, Wei ZH, Liu JX, Liu HY: Lactation-related metabolic mechanism investigated based on mammary gland metabolomics and 4 biofluids' metabolomics relationships in dairy cows. BMC Genomics. 2017 Dec 2;18(1):936. doi: 10.1186/s12864-017-4314-1. [PubMed:29197344 ]