2-Hydroxy-2-methylbutyric acid (CHEM021642)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 18:08:59 UTC
Update Date2016-11-09 01:17:20 UTC
Accession NumberCHEM021642
Identification
Common Name2-Hydroxy-2-methylbutyric acid
ClassSmall Molecule
DescriptionA branched-chain fatty acid that is 2-methylbutyric acid substituted at C-2 by a hydroxy group.
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Urine
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
2-Hydroxy-2-methylbutyrateGenerator
(+/-)-2-hydroxy-2-methylbutanoateHMDB
(+/-)-2-hydroxy-2-methylbutanoic acidHMDB
(+/-)-2-hydroxy-2-methylbutyric acidHMDB
(+/-)-a-hydroxy-a-methylbutyric acidHMDB
(+/-)-alpha-hydroxy-alpha-methylbutyric acidHMDB
2-Hydroxy-2-methyl butyrateHMDB
2-Hydroxy-2-methyl butyric acidHMDB
2-Hydroxy-2-methyl-butanoateHMDB
2-Hydroxy-2-methyl-butanoic acidHMDB
2-Hydroxy-2-methyl-butyrateHMDB, Generator
2-Hydroxy-2-methyl-butyric acidHMDB
2-Hydroxy-2-methyl-N-butyrateHMDB
2-Hydroxy-2-methyl-N-butyric acidHMDB
2-Hydroxy-2-methylbutanoateHMDB
2-Hydroxy-2-methylbutanoic acidHMDB
2-Methyl-2-hydroxybutyric acidHMDB
a-Hydroxy-a-methyl-butyric acidHMDB
a-Hydroxy-a-methylbutyric acidHMDB
alpha-Hydroxy-alpha-methyl-butyric acidHMDB
alpha-Hydroxy-alpha-methylbutyric acidHMDB
2-Hydroxy-2-methylbutyric acidMeSH
Chemical FormulaC5H10O3
Average Molecular Mass118.131 g/mol
Monoisotopic Mass118.063 g/mol
CAS Registry Number3739-30-8
IUPAC Name2-hydroxy-2-methylbutanoic acid
Traditional Name2-hydroxy-2-methylbutyric acid
SMILESCCC(C)(O)C(O)=O
InChI IdentifierInChI=1S/C5H10O3/c1-3-5(2,8)4(6)7/h8H,3H2,1-2H3,(H,6,7)
InChI KeyMBIQENSCDNJOIY-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as hydroxy fatty acids. These are fatty acids in which the chain bears a hydroxyl group.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentHydroxy fatty acids
Alternative Parents
Substituents
  • Branched fatty acid
  • Hydroxy fatty acid
  • Methyl-branched fatty acid
  • Alpha-hydroxy acid
  • Hydroxy acid
  • Tertiary alcohol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility349 g/LALOGPS
logP0.13ALOGPS
logP0.48ChemAxon
logS0.47ALOGPS
pKa (Strongest Acidic)4.1ChemAxon
pKa (Strongest Basic)-3.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity28.08 m³·mol⁻¹ChemAxon
Polarizability11.73 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-05fu-9100000000-c1a485cb07f0e01d496bSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-010a-9720000000-17fc3516e0b12dfe8891Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)splash10-0kml-9100000000-e255071f7864eb24d52bSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)splash10-0a4m-9000000000-182db94e75153cc5fe7eSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)splash10-0a4l-9000000000-0b6fff2f0bd2398fd3daSpectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-00xr-9400000000-2c345c81c4e7d0adda1fSpectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-00xr-9400000000-2c345c81c4e7d0adda1fSpectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-0udl-3900000000-e3a36ea2735fe0adee10Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0ab9-9000000000-ca684c90aea7a8978860Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-00di-9000000000-7aff4fb32a653cf10765Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-052b-9000000000-d95699a47657772ec28bSpectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-9000000000-dd58382320e8a790d761Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0gi0-6900000000-8ff2da5d9ad778c414d8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0l9r-9400000000-1c799a2ce1690ef0b9b0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-ab6ea008b1316fb4e28dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-6900000000-695acf62fd24b0a8056eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-9100000000-8798c599a99d917ff1d9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ab9-9000000000-4262713c5b9c8e0e7c92Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ab9-9200000000-339b88bdf89fa18818f0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-9000000000-23fdf7ac403bc732b18fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-c91f3f5946e47e0898f1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0900000000-0fb707df87ac8f8919b9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-3900000000-4ac52ee77b52ef304aa7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-0673811c3ca40c50612cSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0001987
FooDB IDFDB022784
Phenol Explorer IDNot Available
KNApSAcK IDC00052118
BiGG IDNot Available
BioCyc IDNot Available
METLIN ID6416
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID86129
ChEBI ID68454
PubChem Compound ID95433
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=22770225
2. Young, Wm. G.; Dillon, Robert T.; Lucas, Howard J. Synthesis of the isomeric 2-butenes. Journal of the American Chemical Society (1929), 51 2528-34.
3. Young, Wm. G.; Dillon, Robert T.; Lucas, Howard J. Synthesis of the isomeric 2-butenes. Journal of the American Chemical Society (1929), 51 2528-34.
4. Amberg A, Rosner E, Dekant W: Biotransformation and kinetics of excretion of tert-amyl-methyl ether in humans and rats after inhalation exposure. Toxicol Sci. 2000 Jun;55(2):274-83.
5. Dekant W, Bernauer U, Rosner E, Amberg A: Biotransformation of MTBE, ETBE, and TAME after inhalation or ingestion in rats and humans. Res Rep Health Eff Inst. 2001 May;(102):29-71; discussion 95-109.
6. Holmes E, Foxall PJ, Spraul M, Farrant RD, Nicholson JK, Lindon JC: 750 MHz 1H NMR spectroscopy characterisation of the complex metabolic pattern of urine from patients with inborn errors of metabolism: 2-hydroxyglutaric aciduria and maple syrup urine disease. J Pharm Biomed Anal. 1997 Jul;15(11):1647-59.
7. Fu X, Kimura M, Iga M, Yamaguchi S: Gas chromatographic-mass spectrometric screening for organic acidemias using dried urine filter paper: determination of alpha-ketoacids. J Chromatogr B Biomed Sci Appl. 2001 Jul 5;758(1):87-94.