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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 23:19:06 UTC
Update Date2022-03-07 02:55:36 UTC
HMDB IDHMDB0038036
Secondary Accession Numbers
  • HMDB38036
Metabolite Identification
Common Name2-Propenyl 3-methylbutanoate
Description2-Propenyl 3-methylbutanoate, also known as allyl isovalerate or 2-propenyl isopentanoate, belongs to the class of organic compounds known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid. 2-Propenyl 3-methylbutanoate is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. 2-Propenyl 3-methylbutanoate is a potentially toxic compound.
Structure
Data?1563863130
Synonyms
ValueSource
2-Propenyl 3-methylbutanoic acidGenerator
3-Methylbutanoic acid 2-propenyl esterMeSH
2-Propenyl isopentanoateHMDB
2-Propenyl isovalerateHMDB
3-Methylbutanoic acid, 2-propenyl esterHMDB
3-Methylbutyric acid, allyl esterHMDB
Allyl 3-methylbutanoateHMDB
Allyl 3-methylbutyrateHMDB
Allyl isopentanoateHMDB
Allyl isovalerateHMDB, MeSH
Allyl isovalerianateHMDB
AllylisovalerateHMDB
Butanoic acid, 3-methyl-, 2-propen-1-yl esterHMDB
Butanoic acid, 3-methyl-, 2-propenyl esterHMDB
Butyric acid, 3-methyl-, allyl esterHMDB
Isovaleric acid, allyl esterHMDB
Chemical FormulaC8H14O2
Average Molecular Weight142.1956
Monoisotopic Molecular Weight142.099379692
IUPAC Nameprop-2-en-1-yl 3-methylbutanoate
Traditional Nameallyl isovalerate
CAS Registry Number2835-39-4
SMILES
CC(C)CC(=O)OCC=C
InChI Identifier
InChI=1S/C8H14O2/c1-4-5-10-8(9)6-7(2)3/h4,7H,1,5-6H2,2-3H3
InChI KeyHOMAGVUCNZNWBC-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

Biological location

Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point161.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility475.7 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP2.462 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility3.31 g/LALOGPS
logP2.43ALOGPS
logP2.09ChemAxon
logS-1.6ALOGPS
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity40.35 m³·mol⁻¹ChemAxon
Polarizability16.15 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]+131.77431661259
DarkChem[M-H]-129.52231661259
DeepCCS[M+H]+138.0630932474
DeepCCS[M-H]-135.83130932474
DeepCCS[M-2H]-172.1230932474
DeepCCS[M+Na]+147.1330932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
2-Propenyl 3-methylbutanoateCC(C)CC(=O)OCC=C1196.1Standard polar33892256
2-Propenyl 3-methylbutanoateCC(C)CC(=O)OCC=C924.2Standard non polar33892256
2-Propenyl 3-methylbutanoateCC(C)CC(=O)OCC=C969.2Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - 2-Propenyl 3-methylbutanoate EI-B (Non-derivatized)splash10-052u-9000000000-7354044a3e73badab5472017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 2-Propenyl 3-methylbutanoate EI-B (Non-derivatized)splash10-052u-9000000000-7354044a3e73badab5472018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Propenyl 3-methylbutanoate GC-MS (Non-derivatized) - 70eV, Positivesplash10-052f-9100000000-8c72ffff21927ecdaed82017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Propenyl 3-methylbutanoate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-0a4u-9000000000-144259e1f020cb7f39b72014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Propenyl 3-methylbutanoate 10V, Positive-QTOFsplash10-0006-9800000000-c1c58cf36f0fc42f665d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Propenyl 3-methylbutanoate 20V, Positive-QTOFsplash10-0006-9000000000-79d35f58be29e09f9c342016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Propenyl 3-methylbutanoate 40V, Positive-QTOFsplash10-052f-9000000000-79e7855d5c6b4384458a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Propenyl 3-methylbutanoate 10V, Negative-QTOFsplash10-000x-9800000000-2050888b2f1aa71760e12016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Propenyl 3-methylbutanoate 20V, Negative-QTOFsplash10-0zgi-9500000000-62023d4b0cc8031ce8002016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Propenyl 3-methylbutanoate 40V, Negative-QTOFsplash10-0a5i-9000000000-74d59f47280519a970b82016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Propenyl 3-methylbutanoate 10V, Negative-QTOFsplash10-0a4i-9100000000-9581f7dd0f1122c0bce52021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Propenyl 3-methylbutanoate 20V, Negative-QTOFsplash10-0a4i-9200000000-b681809035a0144971572021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Propenyl 3-methylbutanoate 40V, Negative-QTOFsplash10-053r-9100000000-bfa8683a2fd26729f60e2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Propenyl 3-methylbutanoate 10V, Positive-QTOFsplash10-0f7c-9500000000-5ccc91bfcd244fb824452021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Propenyl 3-methylbutanoate 20V, Positive-QTOFsplash10-052f-9000000000-3546ef42470e2cefd6112021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Propenyl 3-methylbutanoate 40V, Positive-QTOFsplash10-052f-9000000000-5bb1bf863e5ad8e0b7272021-09-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB017246
KNApSAcK IDNot Available
Chemspider ID16835
KEGG Compound IDC19318
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound17816
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1003061
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.