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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 22:57:47 UTC
Update Date2019-07-23 06:24:35 UTC
HMDB IDHMDB0037703
Secondary Accession Numbers
  • HMDB37703
Metabolite Identification
Common NameIsobutyl cinnamate
DescriptionIsobutyl cinnamate belongs to the class of organic compounds known as cinnamic acid esters. These are compound containing an ester derivative of cinnamic acid. Isobutyl cinnamate is a sweet, balsam, and fruity tasting compound. Based on a literature review very few articles have been published on Isobutyl cinnamate.
Structure
Data?1563863075
Synonyms
ValueSource
Isobutyl cinnamic acidGenerator
2-Methylpropyl (2E)-3-phenylprop-2-enoateHMDB
2-Methylpropyl 3-phenyl-2-propenoateHMDB
2-Methylpropyl 3-phenylpropenoateHMDB
2-Methylpropyl beta-phenylacrylateHMDB
2-Methylpropyl cinnamateHMDB
2-Propenoic acid, 3-phenyl-, 2-methylpropyl esterHMDB
Cinnamic acid, isobutyl esterHMDB
FEMA 2193HMDB
Isobutyl (2E)-3-phenyl-2-propenoateHMDB
Isobutyl 3-phenylpropenoateHMDB
Isobutyl beta-phenylacrylateHMDB
Isobutyl cinammateHMDB
LabdanolHMDB
2-Methylpropyl (2Z)-3-phenylprop-2-enoic acidGenerator
Chemical FormulaC13H16O2
Average Molecular Weight204.2649
Monoisotopic Molecular Weight204.115029756
IUPAC Name2-methylpropyl (2Z)-3-phenylprop-2-enoate
Traditional Name2-methylpropyl (2Z)-3-phenylprop-2-enoate
CAS Registry Number122-67-8
SMILES
CC(C)COC(=O)\C=C/C1=CC=CC=C1
InChI Identifier
InChI=1S/C13H16O2/c1-11(2)10-15-13(14)9-8-12-6-4-3-5-7-12/h3-9,11H,10H2,1-2H3/b9-8-
InChI KeyIQZUZPKOFSOVET-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 Solubility0.024 g/LALOGPS
logP10(3.76) g/LALOGPS
logP10(3.76) g/LChemAxon
logS10(-3.9) g/LALOGPS
pKa (Strongest Basic)-6.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity61.57 m³·mol⁻¹ChemAxon
Polarizability23.64 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]+148.25731661259
DarkChem[M-H]-149.06731661259
DeepCCS[M+H]+146.75130932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Isobutyl cinnamateCC(C)COC(=O)\C=C/C1=CC=CC=C12233.3Standard polar33892256
Isobutyl cinnamateCC(C)COC(=O)\C=C/C1=CC=CC=C11555.9Standard non polar33892256
Isobutyl cinnamateCC(C)COC(=O)\C=C/C1=CC=CC=C11643.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Isobutyl cinnamate GC-MS (Non-derivatized) - 70eV, Positivesplash10-0kal-6900000000-9cae211ce75418f614aa2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Isobutyl 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 - Isobutyl cinnamate 10V, Positive-QTOFsplash10-0a4i-9470000000-1e4a99ea35c45b8e00532017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isobutyl cinnamate 20V, Positive-QTOFsplash10-0a4i-9300000000-fa99a6e5cb3c741fba602017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isobutyl cinnamate 40V, Positive-QTOFsplash10-0a4i-9100000000-d24b9d2a323987edfdbc2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isobutyl cinnamate 10V, Negative-QTOFsplash10-0ufr-2790000000-549bc54903e61ffca63c2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isobutyl cinnamate 20V, Negative-QTOFsplash10-0fba-2920000000-cee39e15987fad1dc4f42017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isobutyl cinnamate 40V, Negative-QTOFsplash10-0fb9-3900000000-68dc3ff41a2d9f169d412017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isobutyl cinnamate 10V, Positive-QTOFsplash10-053r-0910000000-a14957ec39570400c46f2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isobutyl cinnamate 20V, Positive-QTOFsplash10-0ue9-3900000000-bf2e585638a67a2707aa2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isobutyl cinnamate 40V, Positive-QTOFsplash10-0udi-5900000000-c8a913c27cb30dbd0f972021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isobutyl cinnamate 10V, Negative-QTOFsplash10-0udi-0190000000-d8e847c45050a7352c862021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isobutyl cinnamate 20V, Negative-QTOFsplash10-0udi-3930000000-164d361ba715f8ce96132021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isobutyl cinnamate 40V, Negative-QTOFsplash10-0fb9-9800000000-a13ba6c2e0d7be73c23c2021-09-22Wishart 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 IDFDB016831
KNApSAcK IDNot Available
Chemspider ID21428207
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound1712057
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.. .