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Record Information
Version3.6
Creation Date2006-08-12 20:46:08 UTC
Update Date2016-02-11 01:06:17 UTC
HMDB IDHMDB03441
Secondary Accession NumbersNone
Metabolite Identification
Common NameCinnamaldehyde
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.
Structure
Thumb
Synonyms
ValueSource
(e)-3-Phenyl-2-propenalChEBI
(e)-3-Phenyl-propenalChEBI
(e)-3-PhenylpropenalChEBI
(e)-CinnamaldehydeChEBI
(e)-Cinnamic aldehydeChEBI
(e)-Phenylvinyl aldehydeChEBI
3-PhenylacrylaldehydeChEBI
trans-Cinnamic aldehydeChEBI
(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
Chemical FormulaC9H8O
Average Molecular Weight132.1592
Monoisotopic Molecular Weight132.057514878
IUPAC Name(2E)-3-phenylprop-2-enal
Traditional Namecinnamal
CAS Registry Number104-55-2
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 KeyInChIKey=KJPRLNWUNMBNBZ-QPJJXVBHSA-N
Chemical Taxonomy
DescriptionThis compound 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
  • Phenylpropene
  • Styrene
  • Benzenoid
  • Monocyclic benzene moiety
  • Enal
  • Alpha,beta-unsaturated aldehyde
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aldehyde
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
StatusDetected but not Quantified
Origin
  • Plant
BiofunctionNot Available
Application
  • Flavoring and aroma agent
Cellular locations
  • Membrane (predicted from logP)
Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point-7.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1.42 mg/mL at 25 °CNot Available
LogP1.90HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility0.41 mg/mLALOGPS
logP2ALOGPS
logP1.98ChemAxon
logS-2.5ALOGPS
pKa (Strongest Basic)-4.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity42.13 m3·mol-1ChemAxon
Polarizability14.48 Å3ChemAxon
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-MSNot Available
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
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biofluid Locations
  • Feces
Tissue Location
  • Neuron
  • Skin
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB008781
KNApSAcK IDC00002725
Chemspider ID553117
KEGG Compound IDC00903
BioCyc IDCINNAMALDEHYDE
BiGG IDNot Available
Wikipedia LinkCinnamaldehyde
NuGOwiki LinkHMDB03441
Metagene LinkHMDB03441
METLIN ID6931
PubChem Compound637511
PDB IDNot Available
ChEBI ID16731
References
Synthesis ReferenceLiu, Xue-mei. Synthesis of cinnamaldehyde. Qufu Shifan Daxue Xuebao, Ziran Kexueban (2005), 31(2), 96-98.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. 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. [15046718 ]
  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. [6334604 ]
  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. [11042091 ]
  4. 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. [11486835 ]
  5. 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. [12582388 ]