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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 22:57:50 UTC
Update Date2019-07-23 06:24:36 UTC
HMDB IDHMDB0037704
Secondary Accession Numbers
  • HMDB37704
Metabolite Identification
Common NameIsoamyl cinnamate
DescriptionIsoamyl cinnamate belongs to the class of organic compounds known as cinnamic acid esters. These are compound containing an ester derivative of cinnamic acid. Isoamyl cinnamate is an amber, cocoa, and floral tasting compound. Based on a literature review very few articles have been published on Isoamyl cinnamate.
Structure
Data?1563863076
Synonyms
ValueSource
Isoamyl cinnamic acidGenerator
2-Propenoic acid, 3-phenyl-, 3-methylbutyl esterHMDB
3-Methylbutyl (2E)-3-phenylacrylateHMDB
3-Methylbutyl 3-phenyl-2-propenoateHMDB
3-Phenyl-3-methylbutyl ester(e)-2-propenoic acidHMDB
3-Phenyl-acrylic acid, 3-methyl-butyl esterHMDB
Cinnamic acid, isopentyl esterHMDB
Cinnamic acid, isopentyl ester (8ci)HMDB
FEMA 2063HMDB
Isoamyl 3-phenyl propenoateHMDB
Isoamyl beta-phenylacrylateHMDB
Isopentyl (2E)-3-phenyl-2-propenoateHMDB
Isopentyl 3-phenylacrylateHMDB
Isopentyl 3-phenylpropenoateHMDB
Isopentyl alcohol, cinnamateHMDB
Isopentyl beta-phenylacrylateHMDB
Isopentyl cinnamateHMDB
3-Methylbutyl (2Z)-3-phenylprop-2-enoic acidGenerator
Chemical FormulaC14H18O2
Average Molecular Weight218.2915
Monoisotopic Molecular Weight218.13067982
IUPAC Name3-methylbutyl (2Z)-3-phenylprop-2-enoate
Traditional Name3-methylbutyl (2Z)-3-phenylprop-2-enoate
CAS Registry Number7779-65-9
SMILES
CC(C)CCOC(=O)\C=C/C1=CC=CC=C1
InChI Identifier
InChI=1S/C14H18O2/c1-12(2)10-11-16-14(15)9-8-13-6-4-3-5-7-13/h3-9,12H,10-11H2,1-2H3/b9-8-
InChI KeyJFHCDEYLWGVZMX-HJWRWDBZSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as cinnamic acid esters. These are compound containing an ester derivative of cinnamic acid.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCinnamic acids and derivatives
Sub ClassCinnamic acid esters
Direct ParentCinnamic acid esters
Alternative Parents
Substituents
  • Cinnamic acid ester
  • Styrene
  • Fatty acid ester
  • Monocyclic benzene moiety
  • Benzenoid
  • Fatty acyl
  • Enoate ester
  • Alpha,beta-unsaturated carboxylic ester
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Organic oxygen compound
  • Carbonyl group
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Source

Route of exposure

Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.007 g/LALOGPS
logP10(4.36) g/LALOGPS
logP10(4.13) g/LChemAxon
logS10(-4.5) g/LALOGPS
pKa (Strongest Basic)-6.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity66.25 m³·mol⁻¹ChemAxon
Polarizability25.36 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+154.24431661259
DarkChem[M-H]-152.831661259
DeepCCS[M+H]+152.30430932474
DeepCCS[M-H]-149.94630932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Isoamyl cinnamateCC(C)CCOC(=O)\C=C/C1=CC=CC=C12302.3Standard polar33892256
Isoamyl cinnamateCC(C)CCOC(=O)\C=C/C1=CC=CC=C11647.4Standard non polar33892256
Isoamyl cinnamateCC(C)CCOC(=O)\C=C/C1=CC=CC=C11750.5Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Isoamyl cinnamate GC-MS (Non-derivatized) - 70eV, Positivesplash10-0f8c-9800000000-884f510d4e960dfd19382017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Isoamyl cinnamate 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 - Isoamyl cinnamate 10V, Positive-QTOFsplash10-014i-4390000000-4bc71b240bdfbcb139c92017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isoamyl cinnamate 20V, Positive-QTOFsplash10-00e9-9510000000-ce0aab329c8292fca7be2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isoamyl cinnamate 40V, Positive-QTOFsplash10-0pi3-9200000000-893bfbccd58675ff778e2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isoamyl cinnamate 10V, Negative-QTOFsplash10-016r-3790000000-572059e9d9aac67efeb32017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isoamyl cinnamate 20V, Negative-QTOFsplash10-002b-1910000000-961751ef38f92ff46d542017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isoamyl cinnamate 40V, Negative-QTOFsplash10-0fb9-3900000000-e152329507041c2cd4d22017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isoamyl cinnamate 10V, Negative-QTOFsplash10-0gb9-0590000000-8155de8e7469e25e92ad2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isoamyl cinnamate 20V, Negative-QTOFsplash10-0006-9530000000-4f932d941dcc7778fc362021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isoamyl cinnamate 40V, Negative-QTOFsplash10-0ufr-7900000000-b237c85e0a3ddcde5ba42021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isoamyl cinnamate 10V, Positive-QTOFsplash10-00lr-0950000000-ebf97cf963e0b48351b82021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isoamyl cinnamate 20V, Positive-QTOFsplash10-0ue9-1900000000-94beed13960d146759ed2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isoamyl cinnamate 40V, Positive-QTOFsplash10-0udi-8900000000-f55f11794d783260bedc2021-09-22Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • 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 IDFDB016832
KNApSAcK IDNot Available
Chemspider ID21428204
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound25021803
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
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.. .