Record Information
Version1.0
Creation date2015-05-07 19:56:26 UTC
Update date2019-11-26 03:21:52 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
2E)-3-Phenyl-2-propenalPhytoBank
(E)-3-PhenylacroleinPhytoBank
(E)-3-Phenylprop-2-en-1-alPhytoBank
(E)-3-Phenylprop-2-enalPhytoBank
(E)-3-Phenylprop-2-enonePhytoBank
E-Cinnamyl aldehydePhytoBank
trans-3-PhenylpropenalPhytoBank
trans-BenzenepropenalPhytoBank
3-Phenyl-2-propenalPhytoBank
3-Phenyl-2-propene-1-alPhytoBank
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
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
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
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MS(E)-3-Phenyl-2-propenal, non-derivatized, GC-MS Spectrumsplash10-0059-3900000000-52db83b595237437ab08Spectrum
GC-MS(E)-3-Phenyl-2-propenal, non-derivatized, GC-MS Spectrumsplash10-0f89-5900000000-540c43f6893b35e8a105Spectrum
GC-MS(E)-3-Phenyl-2-propenal, non-derivatized, GC-MS Spectrumsplash10-0f89-5900000000-482f8b5c30c53689d8ebSpectrum
GC-MS(E)-3-Phenyl-2-propenal, non-derivatized, GC-MS Spectrumsplash10-001i-3900000000-9d274f5e3981ab662650Spectrum
GC-MS(E)-3-Phenyl-2-propenal, non-derivatized, GC-MS Spectrumsplash10-001i-0900000000-4f0ad7748ac21b7320c9Spectrum
GC-MS(E)-3-Phenyl-2-propenal, non-derivatized, GC-MS Spectrumsplash10-0f89-6900000000-ecaba4b9d657020c3f4cSpectrum
GC-MS(E)-3-Phenyl-2-propenal, non-derivatized, GC-MS Spectrumsplash10-001i-0900000000-c02b7869dea8f1113cb4Spectrum
GC-MS(E)-3-Phenyl-2-propenal, non-derivatized, GC-MS Spectrumsplash10-001i-2900000000-d89aa99ef7a6ae16b942Spectrum
GC-MS(E)-3-Phenyl-2-propenal, non-derivatized, GC-MS Spectrumsplash10-0ugi-8900000000-14f14e29c81360ebdd4bSpectrum
GC-MS(E)-3-Phenyl-2-propenal, non-derivatized, GC-MS Spectrumsplash10-0059-3900000000-52db83b595237437ab08Spectrum
Predicted GC-MS(E)-3-Phenyl-2-propenal, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0f89-4900000000-e9eb0053986096f21c83Spectrum
Predicted GC-MS(E)-3-Phenyl-2-propenal, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0a59-5900000000-a125425df0f09bb011292012-07-25View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-056r-9300000000-043ea317ed08a1cbacfb2012-07-25View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-004i-9000000000-39ab07ef5d737e8516712012-07-25View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positivesplash10-0f89-5900000000-f27dd11a8900d729bd192012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (JEOL JMS-D-3000) , Positivesplash10-0f89-5900000000-4e11cf955911f9ca7da22012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (SHIMADZU QP-1000) , Positivesplash10-001i-3900000000-9d274f5e3981ab6626502012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (SHIMADZU QP-1000) , Positivesplash10-001i-0900000000-4f0ad7748ac21b7320c92012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-6M) , Positivesplash10-0f89-6900000000-e363e674a4ec6e092f262012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - CI-B (HITACHI M-80) , Positivesplash10-001i-0900000000-c02b7869dea8f1113cb42012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-6M) , Positivesplash10-001i-2900000000-7339e3ff66ab63ba34092012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positivesplash10-0ugi-8900000000-1b72d0d216af153654442012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-067i-2900000000-76d2db81f3822a698f0a2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-067i-2900000000-76d2db81f3822a698f0a2017-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-1900000000-4b1b083c8fdb2a27206b2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00lr-2900000000-eee6045375789bd7b5112016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f6x-9400000000-ffef407879854d06bd7e2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0900000000-074611feed644fd89c072016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0900000000-cbf5bec188b738c514af2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01p6-9600000000-5eb930cf87b199a5f4492016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-827b27666b5028c8cf772021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0900000000-138b8c24fd394024a31a2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9200000000-93f143b30bbb2b4ff7782021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00lu-2900000000-eda42d3592c23cd1e4bd2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-5900000000-5757a78bf103c73ab4342021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fvi-9300000000-8784eab3c86fc7a1a7212021-09-23View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, Methanol, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CD3OD, experimental)Spectrum
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