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Identification
YMDB IDYMDB00441
Name2-hydroxybutyric acid
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
Description2-Hydroxybutyric acid, also known as a-hydroxybutyrate, 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 is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 2-Hydroxybutyric acid exists in all living species, ranging from bacteria to humans. 2-Hydroxybutyric acid is a potentially toxic compound.
Structure
Thumb
Synonyms
  • (RS)-2-Hydroxybutyrate
  • (RS)-2-Hydroxybutyric acid
  • 1-Hydroxypropane
  • 1-Propanol
  • 1-Propyl alcohol
  • 2-hydroxy-Butanoate
  • 2-hydroxy-Butanoic acid
  • 2-hydroxy-DL-Butyrate
  • 2-hydroxy-DL-Butyric acid
  • 2-Hydroxy-n-butyrate
  • 2-Hydroxy-n-butyric acid
  • 2-Hydroxybutanoate
  • 2-Hydroxybutanoic acid
  • 2-Hydroxybutyrate
  • 2-Hydroxybutyric acid
  • a-Hydroxy-n-butyrate
  • a-Hydroxy-n-butyric acid
  • a-Hydroxybutanoate
  • a-Hydroxybutanoic acid
  • a-Hydroxybutyrate
  • a-Hydroxybutyric acid
  • alpha-hydroxy-n-butyrate
  • alpha-hydroxy-n-butyric acid
  • alpha-Hydroxybutanoate
  • alpha-Hydroxybutanoic acid
  • alpha-Hydroxybutyrate
  • alpha-Hydroxybutyric acid
  • Butanoic acid, 2-hydroxy-
  • Butyric acid, 2-hydroxy-
  • DL-2-Hydroxybutanoate
  • DL-2-Hydroxybutanoic acid
  • DL-a-Hydroxybutyrate
  • DL-a-Hydroxybutyric acid
  • DL-alpha-Hydroxybutyrate
  • DL-alpha-Hydroxybutyric acid
  • Ethylcarbinol
  • n-Propan-1-ol
  • n-Propanol
  • n-Propyl alcohol
  • n-Propyl alkohol
  • Optal
  • Osmosol extra
  • Propan-1-ol
  • Propanol
  • Propanol-1
  • Propyl alcohol
  • Propylan-propyl alcohol
  • Propylic alcohol
  • Α-hydroxybutanoate
  • Α-hydroxybutanoic acid
  • Α-hydroxybutyrate
  • Α-hydroxybutyric acid
  • 2-Hydroxybutyric acid, (R)-isomer
  • 2-Hydroxybutyric acid, monosodium salt
  • 2-Hydroxybutyric acid, (+-)-isomer
  • 2-Hydroxybutyric acid, monosodium salt, (+-)-isomer
  • (+/-)a-hydoxy butyrate
  • (+/-)a-hydoxy butyric acid
  • (+/-)alpha-hydoxy butyrate
  • (+/-)α-hydoxy butyrate
  • (+/-)α-hydoxy butyric acid
CAS number71-23-8
WeightAverage: 104.1045
Monoisotopic: 104.047344122
InChI KeyAFENDNXGAFYKQO-UHFFFAOYSA-N
InChIInChI=1S/C4H8O3/c1-2-3(5)4(6)7/h3,5H,2H2,1H3,(H,6,7)
IUPAC Name2-hydroxybutanoic acid
Traditional IUPAC Nameα-hydroxybutyric acid
Chemical FormulaC4H8O3
SMILESCCC(O)C(O)=O
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
Charge0
Melting point44.2 °C
Experimental Properties
PropertyValueReference
Water Solubility1000 mg/mL at 25 oC [RIDDICK,JA et al. (1986)]PhysProp
LogP0.25 [HANSCH,C ET AL. (1995)]PhysProp
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
Biological Properties
Cellular Locations
  • extracellular
  • cytoplasm
Organoleptic PropertiesNot Available
SMPDB PathwaysNot Available
KEGG Pathways
Propanoate metabolismec00640 Map00640
SMPDB ReactionsNot Available
KEGG Reactions
NAD + 2-hydroxybutyric acidNADH + hydron + 2-Ketobutyric acid
Concentrations
Intracellular Concentrations
Intracellular ConcentrationSubstrateGrowth ConditionsStrainCitation
1725 ± 86 µM YEB media with 0.5 mM glucoseaerobicBaker's yeastExperimentally Determined
Not Available
Conversion Details Here
Extracellular ConcentrationsNot Available
Spectra
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
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00v0-9520000000-598a2bd61c303327bd8fJSpectraViewer
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
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-9100000000-cef703dc6f30af7834a8JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9000000000-1e7e6e8a895c4c1d51dbJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-4900000000-d0907a0b08e0d829cecaJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0pb9-9200000000-d826b54f814ac185b4dbJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9000000000-3727124ed618f038b514JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
References
References:
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
Synthesis Reference:Carlier, 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.
External Links:
ResourceLink
CHEBI ID1148
HMDB IDHMDB00008
Pubchem Compound ID11266
Kegg IDC05984
ChemSpider ID10792
FOODB IDFDB021867
Wikipedia2-Hydroxybutyric_acid
BioCyc IDCPD-3564