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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-11 17:41:52 UTC
Update Date2023-02-21 17:20:12 UTC
HMDB IDHMDB0031249
Secondary Accession Numbers
  • HMDB31249
Metabolite Identification
Common NameMethyl isobutyrate
DescriptionMethyl isobutyrate, also known as fema 2694, belongs to the class of organic compounds known as methyl esters. These are organic compounds containing a carboxyl group that is esterified with a methyl group. They have the general structure RC(=O)OR', where R=H or organyl group and R'=methyl group. Methyl isobutyrate is an organic compound with the formula CH3O2CCH(CH3)2. Methyl isobutyrate is an apple, floral, and flower tasting compound. methyl isobutyrate has been detected, but not quantified, in several different foods, such as fruits, herbs and spices, pineapples, pomes, and potato. This could make methyl isobutyrate a potential biomarker for the consumption of these foods.
Structure
Data?1677000012
Synonyms
ValueSource
Methyl isobutyric acidGenerator
Methyl 2-methylpropanoateMeSH
2-Methyl-propanoic acid, methyl esterHMDB
FEMA 2694HMDB
Isobutyric acid methyl esterHMDB
Methyl 2-methylpropionateHMDB
Methyl isobutanoateHMDB
Propanoic acid, 2-methyl-, methyl esterHMDB
Chemical FormulaC5H10O2
Average Molecular Weight102.1317
Monoisotopic Molecular Weight102.068079564
IUPAC Namemethyl 2-methylpropanoate
Traditional Namemethyl isobutyrate
CAS Registry Number547-63-7
SMILES
COC(=O)C(C)C
InChI Identifier
InChI=1S/C5H10O2/c1-4(2)5(6)7-3/h4H,1-3H3
InChI KeyBHIWKHZACMWKOJ-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as methyl esters. These are organic compounds containing a carboxyl group that is esterified with a methyl group. They have the general structure RC(=O)OR', where R=H or organyl group and R'=methyl group.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassCarboxylic acid derivatives
Direct ParentMethyl esters
Alternative Parents
Substituents
  • Methyl ester
  • Monocarboxylic acid or derivatives
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effect
Disposition
ProcessNot Available
Role
Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point-84.7 °CNot Available
Boiling Point91.00 to 93.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility9268 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP1.139 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility34.6 g/LALOGPS
logP1.2ALOGPS
logP1.17ChemAxon
logS-0.47ALOGPS
pKa (Strongest Basic)-7.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity26.61 m³·mol⁻¹ChemAxon
Polarizability11.19 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+121.20831661259
DarkChem[M-H]-116.83231661259
DeepCCS[M+H]+125.12230932474
DeepCCS[M-H]-123.0430932474
DeepCCS[M-2H]-158.76330932474
DeepCCS[M+Na]+133.49230932474
AllCCS[M+H]+126.332859911
AllCCS[M+H-H2O]+122.132859911
AllCCS[M+NH4]+130.332859911
AllCCS[M+Na]+131.432859911
AllCCS[M-H]-126.332859911
AllCCS[M+Na-2H]-130.332859911
AllCCS[M+HCOO]-134.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Methyl isobutyrateCOC(=O)C(C)C914.8Standard polar33892256
Methyl isobutyrateCOC(=O)C(C)C637.8Standard non polar33892256
Methyl isobutyrateCOC(=O)C(C)C692.9Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Methyl isobutyrate EI-B (Non-derivatized)splash10-0006-9000000000-cd801699f9c2a557b43f2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Methyl isobutyrate EI-B (Non-derivatized)splash10-0006-9000000000-3e969deccf54a3de9a052017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Methyl isobutyrate CI-B (Non-derivatized)splash10-0fe0-9200000000-a852902f244e902cb44a2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Methyl isobutyrate EI-B (Non-derivatized)splash10-0006-9000000000-036e1ab23d11bbe836022017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Methyl isobutyrate EI-B (Non-derivatized)splash10-0006-9000000000-cd801699f9c2a557b43f2018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Methyl isobutyrate EI-B (Non-derivatized)splash10-0006-9000000000-3e969deccf54a3de9a052018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Methyl isobutyrate CI-B (Non-derivatized)splash10-0fe0-9200000000-a852902f244e902cb44a2018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Methyl isobutyrate EI-B (Non-derivatized)splash10-0006-9000000000-036e1ab23d11bbe836022018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Methyl isobutyrate GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9100000000-a10cecf41a27b2809df82016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Methyl isobutyrate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-0006-9000000000-ee4a74a8e582146334532015-03-01Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl isobutyrate 10V, Positive-QTOFsplash10-0udi-4900000000-4158b3942dd80630a16c2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl isobutyrate 20V, Positive-QTOFsplash10-0fdo-9400000000-1fe485d0af82d169052b2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl isobutyrate 40V, Positive-QTOFsplash10-0006-9000000000-4654b7b7e766fa0a4c2b2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl isobutyrate 10V, Negative-QTOFsplash10-0udi-1900000000-301f5de58f5b6678317e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl isobutyrate 20V, Negative-QTOFsplash10-0udi-4900000000-9dcbeff47e662d7a18422016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl isobutyrate 40V, Negative-QTOFsplash10-0lki-9000000000-f7694af026d7ca6c20ed2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl isobutyrate 10V, Negative-QTOFsplash10-0udi-0900000000-4c159e60dacc58e6ba982021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl isobutyrate 20V, Negative-QTOFsplash10-0udj-7900000000-6a873d93371a96550a582021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl isobutyrate 40V, Negative-QTOFsplash10-0a4l-9000000000-d0e996d0a29f176d044d2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl isobutyrate 10V, Positive-QTOFsplash10-0006-9000000000-0e91a487841f70ea0eac2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl isobutyrate 20V, Positive-QTOFsplash10-006x-9000000000-a5913aa9a7c22ca662282021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl isobutyrate 40V, Positive-QTOFsplash10-0006-9000000000-58c7a6fdbf983f1180bf2021-09-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX labView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen Locations
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Nonalcoholic fatty liver disease (NAFLD)
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Diarrhea-predominant IBS
details
Associated Disorders and Diseases
Disease References
Nonalcoholic fatty liver disease
  1. Raman M, Ahmed I, Gillevet PM, Probert CS, Ratcliffe NM, Smith S, Greenwood R, Sikaroodi M, Lam V, Crotty P, Bailey J, Myers RP, Rioux KP: Fecal microbiome and volatile organic compound metabolome in obese humans with nonalcoholic fatty liver disease. Clin Gastroenterol Hepatol. 2013 Jul;11(7):868-75.e1-3. doi: 10.1016/j.cgh.2013.02.015. Epub 2013 Feb 27. [PubMed:23454028 ]
Diarrhoea predominant irritable bowel syndrome
  1. Ahmed I, Greenwood R, Costello Bde L, Ratcliffe NM, Probert CS: An investigation of fecal volatile organic metabolites in irritable bowel syndrome. PLoS One. 2013;8(3):e58204. doi: 10.1371/journal.pone.0058204. Epub 2013 Mar 13. [PubMed:23516449 ]
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB003279
KNApSAcK IDNot Available
Chemspider ID10571
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkMethyl isobutyrate
METLIN IDNot Available
PubChem Compound11039
PDB IDNot Available
ChEBI ID73689
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1008761
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .