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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-11 17:47:36 UTC
Update Date2022-03-07 02:53:14 UTC
HMDB IDHMDB0032072
Secondary Accession Numbers
  • HMDB32072
Metabolite Identification
Common Name(Z)-Cinnamaldehyde
Description(Z)-Cinnamaldehyde, also known as cis-cinnamic aldehyde, belongs to the class of organic compounds known as cinnamaldehydes. These are organic aromatic compounds containing a cinnamlaldehyde moiety, consisting of a benzene and an aldehyde group to form 3-phenylprop-2-enal (Z)-Cinnamaldehyde is a cinnamon and spicy tasting compound (Z)-Cinnamaldehyde has been detected, but not quantified in, ceylon cinnamons (Cinnamomum verum). This could make (Z)-cinnamaldehyde a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on (Z)-Cinnamaldehyde.
Structure
Data?1563862214
Synonyms
ValueSource
cis-CinnamaldehydeChEBI
cis-Cinnamic aldehydeChEBI
(Z)-CinnamaldehydeHMDB, ChEBI
(Z)-CinnamylaldehydeHMDB
3-Phenyl-(Z)-2-propenalHMDB
Chemical FormulaC9H8O
Average Molecular Weight132.1592
Monoisotopic Molecular Weight132.057514878
IUPAC Name(2Z)-3-phenylprop-2-enal
Traditional Name(2Z)-3-phenylprop-2-enal
CAS Registry Number57194-69-1
SMILES
O=C\C=C/C1=CC=CC=C1
InChI Identifier
InChI=1S/C9H8O/c10-8-4-7-9-5-2-1-3-6-9/h1-8H/b7-4-
InChI KeyKJPRLNWUNMBNBZ-DAXSKMNVSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as cinnamaldehydes. These are organic aromatic compounds containing a cinnamlaldehyde moiety, consisting of a benzene and an aldehyde group to form 3-phenylprop-2-enal.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCinnamaldehydes
Sub ClassNot Available
Direct ParentCinnamaldehydes
Alternative Parents
Substituents
  • Cinnamaldehyde
  • Styrene
  • Benzenoid
  • Monocyclic benzene moiety
  • Enal
  • Alpha,beta-unsaturated aldehyde
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aldehyde
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effect
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point245.00 to 246.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility0 slightlyThe Good Scents Company Information System
LogP2.123 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.41 g/LALOGPS
logP2ALOGPS
logP1.98ChemAxon
logS-2.5ALOGPS
pKa (Strongest Basic)-4.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity42.13 m³·mol⁻¹ChemAxon
Polarizability14.36 ųChemAxon
Number of Rings1ChemAxon
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]+131.22431661259
DarkChem[M-H]-127.03631661259
DeepCCS[M+H]+128.01730932474
DeepCCS[M-H]-124.51730932474
DeepCCS[M-2H]-161.70830932474
DeepCCS[M+Na]+137.10930932474
AllCCS[M+H]+126.732859911
AllCCS[M+H-H2O]+122.032859911
AllCCS[M+NH4]+131.232859911
AllCCS[M+Na]+132.432859911
AllCCS[M-H]-125.932859911
AllCCS[M+Na-2H]-127.532859911
AllCCS[M+HCOO]-129.232859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
(Z)-CinnamaldehydeO=C\C=C/C1=CC=CC=C11962.6Standard polar33892256
(Z)-CinnamaldehydeO=C\C=C/C1=CC=CC=C11208.1Standard non polar33892256
(Z)-CinnamaldehydeO=C\C=C/C1=CC=CC=C11226.2Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - (Z)-Cinnamaldehyde GC-MS (Non-derivatized) - 70eV, Positivesplash10-0f8c-4900000000-9646371bf99f8b256f772017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (Z)-Cinnamaldehyde GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (Z)-Cinnamaldehyde 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 - (Z)-Cinnamaldehyde 10V, Negative-QTOFsplash10-001i-0900000000-074611feed644fd89c072016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (Z)-Cinnamaldehyde 20V, Negative-QTOFsplash10-001i-0900000000-cbf5bec188b738c514af2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (Z)-Cinnamaldehyde 40V, Negative-QTOFsplash10-01p6-9600000000-5eb930cf87b199a5f4492016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (Z)-Cinnamaldehyde 10V, Negative-QTOFsplash10-0udi-0900000000-827b27666b5028c8cf772021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (Z)-Cinnamaldehyde 20V, Negative-QTOFsplash10-0udi-0900000000-138b8c24fd394024a31a2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (Z)-Cinnamaldehyde 40V, Negative-QTOFsplash10-004i-9200000000-93f143b30bbb2b4ff7782021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (Z)-Cinnamaldehyde 10V, Positive-QTOFsplash10-001i-1900000000-4b1b083c8fdb2a27206b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (Z)-Cinnamaldehyde 20V, Positive-QTOFsplash10-00lr-2900000000-eee6045375789bd7b5112016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (Z)-Cinnamaldehyde 40V, Positive-QTOFsplash10-0f6x-9400000000-ffef407879854d06bd7e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (Z)-Cinnamaldehyde 10V, Positive-QTOFsplash10-00lu-2900000000-eda42d3592c23cd1e4bd2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (Z)-Cinnamaldehyde 20V, Positive-QTOFsplash10-0udi-5900000000-5757a78bf103c73ab4342021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (Z)-Cinnamaldehyde 40V, Positive-QTOFsplash10-0fvi-9300000000-8784eab3c86fc7a1a7212021-09-23Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen Locations
  • Feces
  • Saliva
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Not SpecifiedNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB008783
KNApSAcK IDNot Available
Chemspider ID4934372
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound6428995
PDB IDNot Available
ChEBI ID89729
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1093121
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.. .