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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-11 18:57:31 UTC
Update Date2021-10-13 06:39:14 UTC
HMDB IDHMDB0034164
Secondary Accession Numbers
  • HMDB34164
Metabolite Identification
Common Name3-Methylbutyl propanoate
Description3-Methylbutyl propanoate, also known as isopentyl propanoate or 3-methylbutyl propionic acid, belongs to the class of organic compounds known as carboxylic acid esters. These are carboxylic acid derivatives in which the carbon atom from the carbonyl group is attached to an alkyl or an aryl moiety through an oxygen atom (forming an ester group). 3-Methylbutyl propanoate is a sweet, banana, and bitter tasting compound. 3-Methylbutyl propanoate has been detected, but not quantified in, apples (Malus pumila) and roman camomiles (Chamaemelum nobile). This could make 3-methylbutyl propanoate a potential biomarker for the consumption of these foods. 3-Methylbutyl propanoate is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a small amount of articles have been published on 3-Methylbutyl propanoate.
Structure
Data?1563862521
Synonyms
ValueSource
3-Methylbutyl propionateChEBI
Isopentyl propanoateChEBI
Isopentyl propionateChEBI
3-Methylbutyl propionic acidGenerator
Isopentyl propanoic acidGenerator
Isopentyl propionic acidGenerator
3-Methylbutyl propanoic acidGenerator
1-Butanol, 3-methyl-, 1-propanoateHMDB
1-Butanol, 3-methyl-, propanoateHMDB
3-Methyl-1-butyl propanoateHMDB
Dioleyl maleateHMDB
FEMA 2082HMDB
iso-Amyl N-propionateHMDB
iso-Pentyl propionateHMDB
Isoamyl propanoateHMDB
Isoamyl propionateHMDB
Isopentyl alcohol, propionateHMDB
Propionic acid, isopentyl esterHMDB
Chemical FormulaC8H16O2
Average Molecular Weight144.2114
Monoisotopic Molecular Weight144.115029756
IUPAC Name3-methylbutyl propanoate
Traditional Name3-methylbutyl propanoate
CAS Registry Number105-68-0
SMILES
CCC(=O)OCCC(C)C
InChI Identifier
InChI=1S/C8H16O2/c1-4-8(9)10-6-5-7(2)3/h7H,4-6H2,1-3H3
InChI KeyXAOGXQMKWQFZEM-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as carboxylic acid esters. These are carboxylic acid derivatives in which the carbon atom from the carbonyl group is attached to an alkyl or an aryl moiety through an oxygen atom (forming an ester group).
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassCarboxylic acid derivatives
Direct ParentCarboxylic acid esters
Alternative Parents
Substituents
  • Carboxylic acid 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
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point159.00 to 161.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility356.7 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP2.667 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility1.42 g/LALOGPS
logP10(2.63) g/LALOGPS
logP10(2.23) g/LChemAxon
logS10(-2) g/LALOGPS
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity40.46 m³·mol⁻¹ChemAxon
Polarizability17.29 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]+134.04731661259
DarkChem[M-H]-130.30431661259
DeepCCS[M+H]+135.40130932474
DeepCCS[M-H]-132.54530932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
3-Methylbutyl propanoateCCC(=O)OCCC(C)C1209.3Standard polar33892256
3-Methylbutyl propanoateCCC(=O)OCCC(C)C942.4Standard non polar33892256
3-Methylbutyl propanoateCCC(=O)OCCC(C)C993.6Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - 3-Methylbutyl propanoate EI-B (Non-derivatized)splash10-0adi-9000000000-d33d7fd534a8c6063d882017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 3-Methylbutyl propanoate EI-B (Non-derivatized)splash10-0adi-9000000000-d33d7fd534a8c6063d882018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Methylbutyl propanoate GC-MS (Non-derivatized) - 70eV, Positivesplash10-054o-9000000000-9f372b9db0d8d1159bc82016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Methylbutyl propanoate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methylbutyl propanoate 10V, Positive-QTOFsplash10-0002-7900000000-0b05bc06211abe3466db2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methylbutyl propanoate 20V, Positive-QTOFsplash10-05fr-9100000000-4c74cc998be99116996b2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methylbutyl propanoate 40V, Positive-QTOFsplash10-0a4i-9000000000-fe83b40c7605f1868e492015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methylbutyl propanoate 10V, Negative-QTOFsplash10-052f-9700000000-ae6e18986cce1b35a8422015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methylbutyl propanoate 20V, Negative-QTOFsplash10-0ab9-9100000000-89d9c9e23cf8147625862015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methylbutyl propanoate 40V, Negative-QTOFsplash10-0a4i-9000000000-beb3655c08cad2b4d3ce2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methylbutyl propanoate 10V, Positive-QTOFsplash10-00di-9000000000-1235af3014d360163db62021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methylbutyl propanoate 20V, Positive-QTOFsplash10-05i0-9000000000-7f1539e860209fb2edc82021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methylbutyl propanoate 40V, Positive-QTOFsplash10-0596-9000000000-b3f98f2ce86c4d0702a62021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methylbutyl propanoate 10V, Negative-QTOFsplash10-00di-9000000000-a18665b48b96b6efae4c2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methylbutyl propanoate 20V, Negative-QTOFsplash10-00di-9000000000-04816fda9d44dd17e57c2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methylbutyl propanoate 40V, Negative-QTOFsplash10-00di-9000000000-62450bd0e995e6730a312021-09-23Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • 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
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 IDFDB012450
KNApSAcK IDC00053346
Chemspider ID7484
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound7772
PDB IDNot Available
ChEBI ID87419
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1021091
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.. .