Record Information
Version1.0
Creation date2010-04-08 22:08:15 UTC
Update date2018-05-29 00:44:23 UTC
Primary IDFDB008781
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name3-Phenyl-2-propenal
DescriptionCinnamaldehyde is the organic compound that gives cinnamon its flavor and odor. This pale yellow viscous liquid occurs naturally in the bark of cinnamon trees and other species of the genus Cinnamomum. The essential oil of cinnamon bark is about 90% cinnamaldehyde. 3-Phenyl-2-propenal is found in many foods, some of which are fig, cloves, anise, and wild celery.
CAS Number104-55-2
Structure
Thumb
Synonyms
SynonymSource
(Z)-CinnamaldehydeHMDB
(Z)-CinnamylaldehydeHMDB
3-Phenyl-(Z)-2-propenalHMDB
cis-CinnamaldehydeHMDB
cis-Cinnamic aldehydeHMDB
(e)-3-Phenyl-propenalChEBI
(e)-Phenylvinyl aldehydeChEBI
2-Propenal, 3-phenyl-biospider
2-Propenaldehyde, 3-phenyl-biospider
3-FenylpropenalHMDB
3-Phenyl-2-propen-1-albiospider
3-Phenyl-2-propenaldehydebiospider
3-Phenylacroleindb_source
3-Phenylacrylaldehydebiospider
3-Phenylprop-2-enalbiospider
3-Phenylprop-2-enaldehydebiospider
3-Phenylpropenalbiospider
Benzylideneacetaldehydebiospider
beta-Phenylacroleinbiospider
beta-Phenylcroleinbiospider
Cinnamaldb_source
CinnamaldehydeChEBI
Cinnamaldehyde, 8CIdb_source
Cinnamic aldehydedb_source
Cinnamyl aldehydebiospider
CinnamylaldehydeHMDB
CinnemaldehydeHMDB
FEMA 2286db_source
Propenaldehyde, 3-phenyl-biospider
Zimtaldehydebiospider
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
Polarizability14.36 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC9H8O
IUPAC name(2Z)-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-DAXSKMNVSA-N
Isomeric SMILESO=C\C=C/C1=CC=CC=C1
Average Molecular Weight132.1592
Monoisotopic Molecular Weight132.057514878
Classification
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
  • 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
Disposition

Route of exposure:

Source:

Biological location:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateLiquid
Physical DescriptionNot Available
Mass CompositionC 81.79%; H 6.10%; O 12.11%DFC
Melting Point-7.5 oC
Boiling PointNot Available
Experimental Water Solubility1.42 mg/mL at 25 oCVALVANI,SC et al. (1981)
Experimental logP1.90HANSCH,C ET AL. (1995)
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
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0f8c-4900000000-9646371bf99f8b256f77View 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
ChemSpider ID553117
ChEMBL IDCHEMBL293492
KEGG Compound IDC00903
Pubchem Compound ID637511
Pubchem Substance IDNot Available
ChEBI ID16731
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB03441
CRC / DFC (Dictionary of Food Compounds) IDDXH04-W:DXH04-W
EAFUS ID641
Dr. Duke IDCINNAMIC-ALDEHYDE|CINNAMALDEHYDE
BIGG IDNot Available
KNApSAcK IDC00002725
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDrw1002631
SuperScent ID637511
Wikipedia IDCinnamaldehyde
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
acaricide22153 A substance used to destroy pests of the subclass Acari (mites and ticks).DUKE
adrenergic37962 Any agent that acts on an adrenergic receptor or affects the life cycle of an adrenergic transmitter.DUKE
allelochemicDUKE
allergenic50904 A chemical compound which causes the onset of an allergic reaction by interacting with any of the molecular pathways involved in an allergy.DUKE
anestheticDUKE
anti aggregantDUKE
anti bacterial33282 A substance that kills or slows the growth of bacteria.DUKE
anti enterococcicDUKE
anti escherichicDUKE
anti herpetic22587 A substance that destroys or inhibits replication of viruses.DUKE
anti inflammatory35472 A substance that reduces or suppresses inflammation.DUKE
anti klebsiellicDUKE
anti leukemic35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
anti mutagenicDUKE
anti pneumonic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti pseudomonic33282 A substance that kills or slows the growth of bacteria.DUKE
anti pyretic35493 A drug that prevents or reduces fever by lowering the body temperature from a raised state. An antipyretic will not affect the normal body temperature if one does not have fever. Antipyretics cause the hypothalamus to override an interleukin-induced increase in temperature. The body will then work to lower the temperature and the result is a reduction in fever.DUKE
anti salmonella33282 A substance that kills or slows the growth of bacteria.DUKE
anti spasmodic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti staphylococcic33282 A substance that kills or slows the growth of bacteria.DUKE
anti ulcer49201 One of various classes of drugs with different action mechanisms used to treat or ameliorate peptic ulcer or irritation of the gastrointestinal tract.DUKE
anti urease50635 EC 3.5.1.* (non-peptide linear amide C-N hydrolase) inhibitor that interferes with the activity of urease (EC 3.5.1.5), reducing hydrolysis.DUKE
anti viral22587 A substance that destroys or inhibits replication of viruses.DUKE
cancer preventive35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
candidicideDUKE
cholereticDUKE
chronotropicDUKE
circulatory stimulantDUKE
central nervous system depressant35470 A class of drugs producing both physiological and psychological effects through a variety of mechanisms involving the central nervous system.DUKE
central nervous system stimulant35470 A class of drugs producing both physiological and psychological effects through a variety of mechanisms involving the central nervous system.DUKE
cyclooxygenase-2 inhibitor50629 A cyclooxygenase inhibitor that interferes with the action of cyclooxygenase 2.DUKE
cyclooxygenase inhibitor35544 A compound or agent that combines with cyclooxygenases (EC 1.14.99.1) and thereby prevents its substrate-enzyme combination with arachidonic acid and the formation of icosanoids, prostaglandins, and thromboxanes.DUKE
cytotoxic52209 A role played by the molecular entity or part thereof which causes the development of a pathological process.DUKE
flavor48318 A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.DUKE
fungicide24127 A substance used to destroy fungal pests.DUKE
herbicide24527 A substance used to destroy plant pests.DUKE
histaminicDUKE
hypoglycemic35526 A drug which lowers the blood glucose level.DUKE
hypotensiveDUKE
hypothermicDUKE
inotropicDUKE
insecticide24852 Strictly, a substance intended to kill members of the class Insecta. In common usage, any substance used for preventing, destroying, repelling or controlling insects.DUKE
irritantDUKE
lipoxygenase inhibitor35856 A compound or agent that combines with lipoxygenase and thereby prevents its substrate-enzyme combination with arachidonic acid and the formation of the icosanoid products hydroxyicosatetraenoic acid and various leukotrienes.DUKE
monoaminergicDUKE
mutagenicDUKE
nematicide25491 A substance used to destroy pests of the phylum Nematoda (roundworms).DUKE
perfumery48318 A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.DUKE
pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
sedative35717 A central nervous system depressant used to induce drowsiness or sleep or to reduce psychological excitement or anxiety.DUKE
sprout inhibitor35222 A substance that diminishes the rate of a chemical reaction.DUKE
teratogenic50905 A role played by a chemical compound in biological systems with adverse consequences in embryo developments, leading to birth defects, embryo death or altered development, growth retardation and functional defect.DUKE
termiticideDUKE
tranquilizerDUKE
tyrosinase inhibitor59997 Any EC 1.14.18.* (oxidoreductase acting on paired donors, miscellaneous compound as one donor, incorporating 1 atom of oxygen) inhibitor that interferes with the action of tyrosinase (monophenol monooxygenase), EC 1.14.18.1, an enzyme that catalyses the oxidation of phenols (such as tyrosine) and is widespread in plants and animals.DUKE
vasodilator35620 A drug used to cause dilation of the blood vessels.DUKE
vibriocideDUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
clove
  1. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
cinnamon
  1. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
  2. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
sweet
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
spice
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
red hots
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
warm
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.