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Identification
YMDB IDYMDB01587
Name2-Methylbutyric acid
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
DescriptionEthylmethylacetic acid, also known as alpha-methyl butyric acid or a-methyl butyrate, belongs to the class of organic compounds known as methyl-branched fatty acids. These are fatty acids with an acyl chain that has a methyl branch. Usually, they are saturated and contain only one or more methyl group. However, branches other than methyl may be present. Ethylmethylacetic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Thumb
Synonyms
  • (+/-)-2-methylbutyrate
  • (+/-)-2-methylbutyric acid
  • 2-Ethylpropionate
  • 2-Ethylpropionic acid
  • 2-Methybutyrate
  • 2-Methybutyric acid
  • 2-Methyl butyrate
  • 2-Methyl butyric acid
  • 2-Methylbutanoate
  • 2-Methylbutanoic acid
  • 2-Methylbutyrate
  • 2-Methylbutyrate, (+-)-isomer
  • 2-Methylbutyrate, sodium salt
  • 2-Methylbutyric acid
  • a-Methyl butyrate
  • a-Methyl butyric acid
  • a-Methylbutyrate
  • a-Methylbutyric acid
  • alpha-Methyl butyrate
  • alpha-Methylbutyrate
  • alpha-Methylbutyric acid
  • Butane-2-carboxylate
  • Butane-2-carboxylic acid
  • D-2-Methyl butyrate
  • D-2-Methyl butyric acid
  • DL-2-Methy butyrate
  • DL-2-Methy butyric acid
  • DL-2-Methylbutyrate
  • DL-2-Methylbutyric acid
  • Ethylmethylacetate
  • Ethylmethylacetic acid
  • Methylethylacetate
  • Methylethylacetic acid
  • RS-2-Methylbutyrate
  • α-methyl butyrate
  • α-methyl butyric acid
  • α-methylbutyrate
  • α-methylbutyric acid
  • alpha-Methyl butyric acid
CAS number116-53-0
WeightAverage: 102.1317
Monoisotopic: 102.068079564
InChI KeyWLAMNBDJUVNPJU-UHFFFAOYSA-N
InChIInChI=1S/C5H10O2/c1-3-4(2)5(6)7/h4H,3H2,1-2H3,(H,6,7)
IUPAC Name2-methylbutanoic acid
Traditional IUPAC Name(+-)-2-methylbutyrate
Chemical FormulaC5H10O2
SMILESCCC(C)C(O)=O
Chemical Taxonomy
Description belongs to the class of organic compounds known as methyl-branched fatty acids. These are fatty acids with an acyl chain that has a methyl branch. Usually, they are saturated and contain only one or more methyl group. However, branches other than methyl may be present.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentMethyl-branched fatty acids
Alternative Parents
Substituents
  • Methyl-branched fatty acid
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water Solubility45 mg/mL at 20 oC [RIEMENSCHNEIDER,W (1986)]PhysProp
LogP1.18 [HANSCH,C ET AL. (1995)]PhysProp
Predicted Properties
PropertyValueSource
Water Solubility57.2 g/LALOGPS
logP1.47ALOGPS
logP1.46ChemAxon
logS-0.25ALOGPS
pKa (Strongest Acidic)4.97ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity26.45 m³·mol⁻¹ChemAxon
Polarizability10.98 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular LocationsNot Available
Organoleptic Properties
Flavour/OdourSource
AcidFDB011876
CheeseFDB011876
PungentFDB011876
Roquefort cheeseFDB011876
SourFDB011876
StrawberryFDB011876
SweatFDB011876
SMPDB PathwaysNot Available
KEGG PathwaysNot Available
SMPDB ReactionsNot Available
KEGG ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-05i3-9000000000-0aaa78177c0a6f4e0f30JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-05i3-9000000000-0aaa78177c0a6f4e0f30JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-056r-9000000000-2909ffab0f5a63851edfJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-05dr-9200000000-d03c368f82e8aafbbf2eJSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positivesplash10-05i3-9000000000-1b5a036458bffab2edb2JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udr-9500000000-015593bb5625d47062e0JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4r-9100000000-9cefc93a02ed409afaa7JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-4c09f00d4b395429c15fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udr-9500000000-015593bb5625d47062e0JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4r-9100000000-9cefc93a02ed409afaa7JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-4c09f00d4b395429c15fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-2900000000-91099c4563c2a38048c7JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0pb9-9500000000-614d914711126947b2ccJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-0c48b735fe7cb3bd438fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-2900000000-91099c4563c2a38048c7JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0pb9-9500000000-614d914711126947b2ccJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-0c48b735fe7cb3bd438fJSpectraViewer
MSMass Spectrum (Electron Ionization)splash10-05i0-9000000000-5202133990304f535e3eJSpectraViewer | MoNA
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
References
References:
  • Loscos, N., Hernandez-Orte, P., Cacho, J., Ferreira, V. (2007). "Release and formation of varietal aroma compounds during alcoholic fermentation from nonfloral grape odorless flavor precursors fractions." J Agric Food Chem 55:6674-6684.17616208
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID37070
HMDB IDHMDB02176
Pubchem Compound ID8314
Kegg IDC18319
ChemSpider ID8012
FOODB IDFDB011876
Wikipedia IDNot Available
BioCyc IDNot Available