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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-12 01:44:52 UTC
Update Date2022-03-07 02:56:30 UTC
HMDB IDHMDB0040210
Secondary Accession Numbers
  • HMDB40210
Metabolite Identification
Common Name2-Propenyl hexanoate
Description2-Propenyl hexanoate, also known as allyl caproate, allocopen, or allyl hexanoate is an organic compound with the formula C5H11CO2CH2CH=CH2. It is a colorless liquid, although commercial samples appear yellowish. It occurs naturally in pineapples. It belongs to the class of organic compounds known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid. 2-Propenyl hexanoate is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Allyl hexanoate is employed principally in the formulation of pineapple flavors but it can also be used for peach and apricot essences and for apple blossom, peach blossom, and wisteria perfume compositions. It is an ingredient of some lipstick perfumes. It also adds a sweet juicy note to citrus flavors.
Structure
Data?1563863506
Synonyms
ValueSource
2-Propenyl hexanoic acidGenerator
2-Propenyl N-hexanoateHMDB
AllocopenHMDB
Allyl caproateHMDB, MeSH
Allyl hexanoateHMDB
Allyl N-caproateHMDB
Allyl N-hexanoateHMDB
Allylester kyseliny kapronoveHMDB
FEMA 2032HMDB
Hexanoic acid, 2-propen-1-yl esterHMDB
Hexanoic acid, 2-propenyl esterHMDB
Hexanoic acid, allyl esterHMDB
Chemical FormulaC9H16O2
Average Molecular Weight156.2221
Monoisotopic Molecular Weight156.115029756
IUPAC Nameprop-2-en-1-yl hexanoate
Traditional Nameallyl caproate
CAS Registry Number123-68-2
SMILES
CCCCCC(=O)OCC=C
InChI Identifier
InChI=1S/C9H16O2/c1-3-5-6-7-9(10)11-8-4-2/h4H,2-3,5-8H2,1H3
InChI KeyRCSBILYQLVXLJG-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 DescriptorsNot Available
Ontology
Physiological effect
Disposition
Process
Role
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point185.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility136.1 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP3.128 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.4 g/LALOGPS
logP3.02ALOGPS
logP2.69ChemAxon
logS-2.6ALOGPS
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity45.01 m³·mol⁻¹ChemAxon
Polarizability18.52 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]+138.25531661259
DarkChem[M-H]-135.17631661259
DeepCCS[M+H]+140.20430932474
DeepCCS[M-H]-137.43930932474
DeepCCS[M-2H]-174.51130932474
DeepCCS[M+Na]+149.49930932474
AllCCS[M+H]+139.632859911
AllCCS[M+H-H2O]+135.732859911
AllCCS[M+NH4]+143.332859911
AllCCS[M+Na]+144.332859911
AllCCS[M-H]-139.832859911
AllCCS[M+Na-2H]-141.832859911
AllCCS[M+HCOO]-144.232859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
2-Propenyl hexanoateCCCCCC(=O)OCC=C1376.4Standard polar33892256
2-Propenyl hexanoateCCCCCC(=O)OCC=C1045.8Standard non polar33892256
2-Propenyl hexanoateCCCCCC(=O)OCC=C1105.3Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - 2-Propenyl hexanoate EI-B (Non-derivatized)splash10-0006-9000000000-149d79e35c1f7b309b582017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 2-Propenyl hexanoate EI-B (Non-derivatized)splash10-0006-9000000000-149d79e35c1f7b309b582018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Propenyl hexanoate GC-MS (Non-derivatized) - 70eV, Positivesplash10-0596-9200000000-d882e8ac52bec3e475862017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Propenyl hexanoate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Propenyl hexanoate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-0007-9000000000-bc1f3eeb24010e4237392015-03-01Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Propenyl hexanoate 10V, Positive-QTOFsplash10-0a4i-5900000000-324fa45aced7c63e736b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Propenyl hexanoate 20V, Positive-QTOFsplash10-0a4j-9200000000-d739e4c131c0da9196ba2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Propenyl hexanoate 40V, Positive-QTOFsplash10-052f-9000000000-9b1cf000856114602cda2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Propenyl hexanoate 10V, Negative-QTOFsplash10-0a4j-7900000000-2c258d937145207f61ce2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Propenyl hexanoate 20V, Negative-QTOFsplash10-014j-9600000000-241fe600e52c60c9749b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Propenyl hexanoate 40V, Negative-QTOFsplash10-05mw-9000000000-224150987e6813dde16a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Propenyl hexanoate 10V, Positive-QTOFsplash10-0a4m-9200000000-b6a1d810077f0ce23a0c2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Propenyl hexanoate 20V, Positive-QTOFsplash10-0596-9000000000-196c2e4ed2bba68253822021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Propenyl hexanoate 40V, Positive-QTOFsplash10-0a4l-9000000000-e517694f394d13aba4d92021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Propenyl hexanoate 10V, Negative-QTOFsplash10-0002-9000000000-08ab9ac78c60653a60d62021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Propenyl hexanoate 20V, Negative-QTOFsplash10-00kb-9300000000-8c41d2bdeb5aab6584582021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Propenyl hexanoate 40V, Negative-QTOFsplash10-0002-9000000000-7932c97ff8ef70fb22552021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
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 IDFDB019922
KNApSAcK IDC00053314
Chemspider ID29006
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound31266
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1000731
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.