Record Information
Version1.0
Creation date2015-05-07 19:56:26 UTC
Update date2018-05-29 01:54:54 UTC
Primary IDFDB030727
Secondary Accession Numbers
  • FDB008782
Chemical Information
FooDB Namecinnamaldehyde
DescriptionCinnamaldehyde, also known as (E)-3-phenyl-2-propenal or 3-phenylacrylaldehyde, is a member of the class of compounds known as cinnamaldehydes. Cinnamaldehydes are organic aromatic compounds containing a cinnamlaldehyde moiety, consisting of a benzene and an aldehyde group to form 3-phenylprop-2-enal. Cinnamaldehyde is practically insoluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Cinnamaldehyde is a sweet, candy, and cinnamon tasting compound and can be found in a number of food items such as sour cherry, rubus (blackberry, raspberry), horseradish, and sea-buckthornberry, which makes cinnamaldehyde a potential biomarker for the consumption of these food products. Cinnamaldehyde can be found primarily in feces, as well as in human neuron and skin tissues. Cinnamaldehyde exists in all eukaryotes, ranging from yeast to humans. Cinnamaldehyde is a non-carcinogenic (not listed by IARC) potentially toxic compound. Cinnamaldehyde is an organic compound with the formula C6H5CH=CHCHO. Occurring naturally as predominantly the trans (E) isomer, it gives cinnamon its flavor and odor. It is a flavonoid that is naturally synthesized by the shikimate pathway. This pale yellow, viscous liquid occurs in the bark of cinnamon trees and other species of the genus Cinnamomum. The essential oil of cinnamon bark is about 50% cinnamaldehyde . The specific symptoms that can result from cinnamic aldehyde allergy can vary considerably amongst patients from a severe anaphylactic reaction to asthma, abdominal symptoms, eczema or headaches (L2140) (T3DB).
CAS Number104-55-2
Structure
Thumb
Synonyms
SynonymSource
(e)-3-Phenyl-2-propenalChEBI
(e)-3-Phenyl-propenalChEBI
(e)-3-PhenylpropenalChEBI
(e)-Cinnamic aldehydeChEBI
(e)-Phenylvinyl aldehydeChEBI
3-PhenylacrylaldehydeChEBI
trans-Cinnamic aldehydeChEBI
(e)-CinnamaldehydeHMDB
(2E)-3-Phenyl-2-propenalHMDB
(2E)-3-PhenylacrylaldehydeHMDB
3-FenylpropenalHMDB
3-Phenyl-2-propen-1-alHMDB
3-Phenyl-2-propenaldehydeHMDB
3-PhenylacroleinHMDB
3-Phenylprop-2-enalHMDB
3-PhenylpropenalHMDB
BenzylideneacetaldehydeHMDB
beta-PhenylcroleinHMDB
CinnamalHMDB
Cinnamic aldehydeHMDB
Cinnamyl aldehydeHMDB
CinnamylaldehydeHMDB
CinnemaldehydeHMDB
trans-3-Phenyl-2-propenalHMDB
trans-CinnamaldehydeHMDB
trans-CinnamylaldehydeHMDB
beta-PhenylacroleinHMDB
SupercinnamaldehydeHMDB
trans-3-Phenylprop-2-enaldehydeHMDB
3-Phenylprop-2-enaldehydeHMDB
Cinnamic aldehyde, (e)-isomerHMDB
Predicted 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
Polarizability14.48 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC9H8O
IUPAC name(2E)-3-phenylprop-2-enal
InChI IdentifierInChI=1S/C9H8O/c10-8-4-7-9-5-2-1-3-6-9/h1-8H/b7-4+
InChI KeyKJPRLNWUNMBNBZ-QPJJXVBHSA-N
Isomeric SMILES[H]C(=O)\C=C\C1=CC=CC=C1
Average Molecular Weight132.1592
Monoisotopic Molecular Weight132.057514878
Classification
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 Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0059-3900000000-52db83b595237437ab08View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0f89-5900000000-540c43f6893b35e8a105View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0f89-5900000000-482f8b5c30c53689d8ebView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-001i-3900000000-9d274f5e3981ab662650View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-001i-0900000000-4f0ad7748ac21b7320c9View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0f89-6900000000-ecaba4b9d657020c3f4cView in MoNA
GC-MSGC-MS Spectrum - CI-B (Non-derivatized)splash10-001i-0900000000-c02b7869dea8f1113cb4View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-001i-2900000000-d89aa99ef7a6ae16b942View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0ugi-8900000000-14f14e29c81360ebdd4bView in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0059-3900000000-52db83b595237437ab08View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0f89-4900000000-e9eb0053986096f21c83View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0a59-5900000000-a125425df0f09bb01129View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-056r-9300000000-043ea317ed08a1cbacfbView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-004i-9000000000-39ab07ef5d737e851671View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positivesplash10-0f89-5900000000-f27dd11a8900d729bd19View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (JEOL JMS-D-3000) , Positivesplash10-0f89-5900000000-4e11cf955911f9ca7da2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (SHIMADZU QP-1000) , Positivesplash10-001i-3900000000-9d274f5e3981ab662650View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (SHIMADZU QP-1000) , Positivesplash10-001i-0900000000-4f0ad7748ac21b7320c9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-6M) , Positivesplash10-0f89-6900000000-e363e674a4ec6e092f26View in MoNA
LC-MS/MSLC-MS/MS Spectrum - CI-B (HITACHI M-80) , Positivesplash10-001i-0900000000-c02b7869dea8f1113cb4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-6M) , Positivesplash10-001i-2900000000-7339e3ff66ab63ba3409View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positivesplash10-0ugi-8900000000-1b72d0d216af15365444View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-067i-2900000000-76d2db81f3822a698f0aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-067i-2900000000-76d2db81f3822a698f0aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-1900000000-4b1b083c8fdb2a27206bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00lr-2900000000-eee6045375789bd7b511View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f6x-9400000000-ffef407879854d06bd7eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0900000000-074611feed644fd89c07View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0900000000-cbf5bec188b738c514afView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01p6-9600000000-5eb930cf87b199a5f449View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference