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Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2012-09-11 18:57:22 UTC
Update Date2019-07-23 06:15:20 UTC
HMDB IDHMDB0034161
Secondary Accession Numbers
  • HMDB34161
Metabolite Identification
Common Name2-Methylpropyl butanoate
Description2-Methylpropyl butanoate, also known as butyric acid, isobutyl ester or isobutyl butanoate, belongs to the class of organic compounds known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid. 2-Methylpropyl butanoate is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Data?1563862520
Synonyms
ValueSource
2-Methyl-1-propyl butyrateChEBI
2-Methylpropyl butyrateChEBI
Butanoic acid, 2-methylpropyl esterChEBI
Butanoic acid, isobutyl esterChEBI
Butanoic acid, methyl propyl esterChEBI
Butyric acid, isobutyl esterChEBI
Isobutyl butanoateChEBI
Isobutyl N-butyrateChEBI
2-Methyl-1-propyl butyric acidGenerator
2-Methylpropyl butyric acidGenerator
Butanoate, 2-methylpropyl esterGenerator
Butanoate, isobutyl esterGenerator
Butanoate, methyl propyl esterGenerator
Butyrate, isobutyl esterGenerator
Isobutyl butanoic acidGenerator
Isobutyl N-butyric acidGenerator
2-Methylpropyl butanoic acidGenerator
FEMA 2187HMDB
Isobutyl butyrateHMDB
Isobutyl ester OF butanoic acidHMDB
Isobutyl-N-butyrateHMDB
N-Butyric acid isobutyl esterHMDB
Chemical FormulaC8H16O2
Average Molecular Weight144.2114
Monoisotopic Molecular Weight144.115029756
IUPAC Name2-methylpropyl butanoate
Traditional Name2-methylpropyl butanoate
CAS Registry Number539-90-2
SMILES
CCCC(=O)OCC(C)C
InChI Identifier
InChI=1S/C8H16O2/c1-4-5-8(9)10-6-7(2)3/h7H,4-6H2,1-3H3
InChI KeyRGFNRWTWDWVHDD-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acid esters
Direct ParentFatty acid esters
Alternative Parents
Substituents
  • Fatty acid ester
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility1.72 g/LALOGPS
logP2.65ALOGPS
logP2.31ChemAxon
logS-1.9ALOGPS
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity40.38 m³·mol⁻¹ChemAxon
Polarizability17.06 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-05fu-9000000000-8ca43e86a485b4a1debfSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-05fu-9000000000-caf15cc81f8fd2a7531fSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-05fr-9000000000-89a8fa52be9941be8e10Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-05fu-9000000000-8ca43e86a485b4a1debfSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-05fu-9000000000-caf15cc81f8fd2a7531fSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-05fr-9000000000-89a8fa52be9941be8e10Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0596-9000000000-90bafdff80f05fa2d929Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052b-9600000000-704be4ab2fbc7786d081Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-9000000000-d6ac55edd63a3c7e3840Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-7a53998366f3c0bb5126Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00kf-9800000000-ec011f1d1a1b1f8c0a31Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014u-9100000000-39699396fa1e041b3b24Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00kf-9000000000-540d4752e7b44a702690Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Diarrhea-predominant IBS
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Nonalcoholic fatty liver disease (NAFLD)
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 IDFDB012447
KNApSAcK IDNot Available
Chemspider ID10423
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound10885
PDB IDNot Available
ChEBI ID87683
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  5. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.