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Cinnamaldehyde (CHEM003939)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (2)XML
Record Information
Version1.0
Creation Date2014-10-14 21:19:45 UTC
Update Date2016-11-09 01:09:15 UTC
Accession NumberCHEM003939
Identification
Common NameCinnamaldehyde
ClassSmall Molecule
DescriptionCinnamaldehyde is the aldehyde that gives cinnamon its flavor and odor. Cinnamaldehyde occurs naturally in the bark of cinnamon trees and other species of the genus Cinnamomum like camphor and cassia. These trees are the natural source of cinnamon, and the essential oil of cinnamon bark is about 90% cinnamaldehyde. Cinnamaldehyde is also used as a fungicide. Proven effective on over 40 different crops, cinnamaldehyde is typically applied to the root systems of plants. Its low toxicity and well-known properties make it ideal for agriculture. To a lesser extent, cinnamaldehyde is an effective insecticide, and its scent is also known to repel animals like cats and dogs. Cinnamaldehyde is also known as a corrosion inhibitor for steel and other ferrous alloys in corrosive fluids. It can be used in combination with additional components such as dispersing agents, solvents and other surfactants. Concentrated cinnamaldehyde is a skin irritant, and the chemical is toxic in large doses, but no agencies suspect the compound is a carcinogen or poses a long-term health hazard. Most cinnamaldehyde is excreted in urine as cinnamic acid, an oxidized form of cinnamaldehyde.
Contaminant Sources
  • EAFUS Chemicals
  • FooDB Chemicals
  • HMDB Contaminants - Feces
  • HPV EPA Chemicals
  • STOFF IDENT Compounds
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Food Toxin
  • Industrial/Workplace Toxin
  • Metabolite
  • Natural Compound
  • Pesticide
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
(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
Chemical FormulaC9H8O
Average Molecular Mass132.159 g/mol
Monoisotopic Mass132.058 g/mol
CAS Registry Number104-55-2
IUPAC Name(2E)-3-phenylprop-2-enal
Traditional Namecinnamal
SMILESO=C\C=C\C1=CC=CC=C1
InChI IdentifierInChI=1S/C9H8O/c10-8-4-7-9-5-2-1-3-6-9/h1-8H/b7-4+
InChI KeyKJPRLNWUNMBNBZ-QPJJXVBHSA-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 Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue Locations
  • Neuron
  • Skin
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateLiquid
AppearanceNot Available
Experimental Properties
PropertyValue
Melting Point-7.5 °C
Boiling Point248 C (478 F; 521 K)
Solubility1.42 mg/mL at 25 °C
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
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MSsplash10-0059-3900000000-52db83b595237437ab08View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSsplash10-0f89-4900000000-e9eb0053986096f21c83View in MoNA
GC-MSGC-MS Spectrum - EI-Bsplash10-0f89-5900000000-540c43f6893b35e8a105View in MoNA
GC-MSGC-MS Spectrum - EI-Bsplash10-0f89-5900000000-482f8b5c30c53689d8ebView in MoNA
GC-MSGC-MS Spectrum - EI-Bsplash10-001i-3900000000-9d274f5e3981ab662650View in MoNA
GC-MSGC-MS Spectrum - EI-Bsplash10-001i-0900000000-4f0ad7748ac21b7320c9View in MoNA
GC-MSGC-MS Spectrum - EI-Bsplash10-0f89-6900000000-ecaba4b9d657020c3f4cView in MoNA
GC-MSGC-MS Spectrum - CI-Bsplash10-001i-0900000000-c02b7869dea8f1113cb4View in MoNA
GC-MSGC-MS Spectrum - EI-Bsplash10-001i-2900000000-d89aa99ef7a6ae16b942View in MoNA
GC-MSGC-MS Spectrum - EI-Bsplash10-0ugi-8900000000-14f14e29c81360ebdd4bView in MoNA
GC-MSGC-MS Spectrum - GC-MSsplash10-0059-3900000000-52db83b595237437ab08View 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 Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Toxicity Profile
Route of ExposureInhalation; dermal; ingestion
Mechanism of ToxicityCinnamaldehyde is an allergen. The physiologic effect of cinnamaldehyde is by means of increased histamine release and cell-mediated immunity.
MetabolismCinnamaldehyde is converted to cinnamoyl-CoA by cinnamoyl-CoA reductase.
Toxicity ValuesLD50: 3400 mg/kg (rat, oral)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsAllergic reaction.
SymptomsThe 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. (6)
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0003441
FooDB IDFDB030727
Phenol Explorer IDNot Available
KNApSAcK IDC00035187
BiGG IDNot Available
BioCyc IDNot Available
METLIN ID6931
PDB IDNot Available
Wikipedia LinkCinnamaldehyde
Chemspider ID553117
ChEBI ID16731
PubChem Compound ID637511
Kegg Compound IDC00903
YMDB IDYMDB01654
ECMDB IDNot Available
References
Synthesis ReferenceLiu, Xue-mei. Synthesis of cinnamaldehyde. Qufu Shifan Daxue Xuebao, Ziran Kexueban (2005), 31(2), 96-98.
MSDSNot Available
General References
1. Liu, Xue-mei. Synthesis of cinnamaldehyde. Qufu Shifan Daxue Xuebao, Ziran Kexueban (2005), 31(2), 96-98.
2. Muller G, Biering A, Graubaum K, Jeschkeit H, Neubert K, Kleine R, Klapperstuck M: [The PABA test]. Dtsch Z Verdau Stoffwechselkr. 1984;44(5):219-31.
3. Smith CK, Moore CA, Elahi EN, Smart AT, Hotchkiss SA: Human skin absorption and metabolism of the contact allergens, cinnamic aldehyde, and cinnamic alcohol. Toxicol Appl Pharmacol. 2000 Nov 1;168(3):189-99.
4. Bandell M, Story GM, Hwang SW, Viswanath V, Eid SR, Petrus MJ, Earley TJ, Patapoutian A: Noxious cold ion channel TRPA1 is activated by pungent compounds and bradykinin. Neuron. 2004 Mar 25;41(6):849-57.
5. Smith CK, Cheung C, Elahi EN, Hotchkiss SA: High-performance liquid chromatography method for the quantification of non-radiolabelled cinnamic compounds in analytes derived from human skin absorption and metabolism experiments. J Chromatogr B Biomed Sci Appl. 2001 Jul 15;758(2):249-64.
6. Bruze M, Johansen JD, Andersen KE, Frosch P, Lepoittevin JP, Rastogi S, Wakelin S, White I, Menne T: Deodorants: an experimental provocation study with cinnamic aldehyde. J Am Acad Dermatol. 2003 Feb;48(2):194-200.
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=11975643
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=17140783
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=17662960
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=18218683
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=19845671
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=20431333
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=20955755
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=21266172
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=21388814
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=21394803
17. https://www.ncbi.nlm.nih.gov/pubmed/?term=21466812
18. https://www.ncbi.nlm.nih.gov/pubmed/?term=21469739
19. https://www.ncbi.nlm.nih.gov/pubmed/?term=21517069
20. https://www.ncbi.nlm.nih.gov/pubmed/?term=21603596
21. https://www.ncbi.nlm.nih.gov/pubmed/?term=21708228
22. https://www.ncbi.nlm.nih.gov/pubmed/?term=21767279
23. https://www.ncbi.nlm.nih.gov/pubmed/?term=21788726
24. https://www.ncbi.nlm.nih.gov/pubmed/?term=29079364