Cinnamaldehyde

This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

Name
Cinnamaldehyde
Accession Number
DB14184
Description

Cinnamaldehyde is a naturally occurring flavonoid that gives the spice cinnamon its flavour and odour. It occurs naturally in the bark of cinnamon trees and other species of the genus Cinnamomum such as camphor and cassia.

Sensitivity to cinnamaldehyde may be identified with a clinical patch test.

Type
Small Molecule
Groups
Approved, Experimental
Structure
Thumb
Weight
Average: 132.1592
Monoisotopic: 132.057514878
Chemical Formula
C9H8O
Synonyms
  • (3E)-3-phenylprop-2-enal
  • (E)-3-Phenyl-2-propenal
  • (E)-3-Phenyl-propenal
  • (E)-3-Phenylpropenal
  • 3-phenylacrylaldehyde
  • Cinnamal
  • Cinnamaldehyde
  • trans-Cinnamaldehyde
  • trans-Cinnamic aldehyde
  • Zimtaldehyde

Pharmacology

Indication

Cinnamaldehyde is approved by the FDA for use within allergenic epicutaneous patch tests which are indicated for use as an aid in the diagnosis of allergic contact dermatitis (ACD) in persons 6 years of age and older.

Contraindications & Blackbox Warnings
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Pharmacodynamics
Not Available
Mechanism of action
Not Available
Absorption

Cinnamaldehyde is 52% absorbed through the skin and shown to be rapidly absorbed from the gut 1.

Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination

Cinnamaldehyde is metabolized and excreted primarily in the urine and, to a minor extent, in the feces 1. After oral or intraperitoneal administration to rats and mice, 69–98% of the dose of cinnamaldehyde was recovered in the urine and feces within 24 h 1.

Half-life
Not Available
Clearance
Not Available
Adverse Effects
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Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
Calcium carbimideThe risk or severity of adverse effects can be increased when Calcium carbimide is combined with Cinnamaldehyde.
DisulfiramThe risk or severity of adverse effects can be increased when Disulfiram is combined with Cinnamaldehyde.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

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  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level

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  • Action
    Action

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Food Interactions
Not Available

Products

Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
T.R.U.E. Test Thin-Layer Rapid Use Patch TestCinnamaldehyde (41 ug/48h) + 2,2'-Dibenzothiazyl disulfide (20 ug/48h) + 2-mercaptobenzothiazole (61 ug/48h) + 4-(Isopropylamino)diphenylamine (10 ug/48h) + Bacitracin (486 ug/48h) + Balsam of Peru (648 ug/48h) + Benzocaine (378 ug/48h) + Benzylparaben (162 ug/48h) + Bisphenol A diglycidyl ether (32 ug/48h) + Bromothalonil (4 ug/48h) + Bronopol (203 ug/48h) + Budesonide (0.8 ug/48h) + Butylparaben (162 ug/48h) + Chlorquinaldol (77 ug/48h) + Cinchocaine hydrochloride (66 ug/48h) + Cinnamyl alcohol (63 ug/48h) + Clioquinol (77 ug/48h) + Cobalt chloride hexahydrate (4 ug/48h) + Diazolidinylurea (446 ug/48h) + Potassium dichromate (15.7 ug/48h) + Dipentamethylenethiuram disulfide (5.5 ug/48h) + Diphenylguanidine (68 ug/48h) + Disperse Blue 106 (41 ug/48h) + Disulfiram (5.5 ug/48h) + Ditiocarb zinc (68 ug/48h) + Ethyl hydroxybenzoate (162 ug/48h) + Ethylenediamine (18 ug/48h) + Eugenol (41 ug/48h) + Evernia prunastri (81 ug/48h) + Formaldehyde (146 ug/48h) + Geraniol (81 ug/48h) + Hydrocortisone butyrate (16 ug/48h) + Hydroxycitronellal (63 ug/48h) + Imidurea (486 ug/48h) + Isoeugenol (17 ug/48h) + Lanolin alcohols (810 ug/48h) + Methylchloroisothiazolinone (3 ug/48h) + Methylparaben (162 ug/48h) + Morpholinylmercaptobenzothiazole (20 ug/48h) + N,N'-diphenyl-1,4-phenylenediamine (25 ug/48h) + N-Cyclohexyl-N'-phenyl-1,4-phenylenediamine (25 ug/48h) + Neomycin sulfate (486 ug/48h) + Nickel sulfate hexahydrate (36 ug/48h) + P-Tert-Butylphenol-Formaldehyde Resin (Low Molecular Weight) (36 ug/48h) + Parthenolide (2 ug/48h) + Propylparaben (162 ug/48h) + Quaternium-15 (81 ug/48h) + Rosin (972 ug/48h) + Sodium aurotiosulfate (23 ug/48h) + Tetracaine hydrochloride (66 ug/48h) + Tetramethylthiuram monosulfide (5.5 ug/48h) + Thimerosal (6 ug/48h) + Thiohexam (20 ug/48h) + Thiram (5.5 ug/48h) + Tixocortol pivalate (2 ug/48h) + Zinc dibutyldithiocarbamate (68 ug/48h) + alpha-Amyl cinnamaldehyde (17 ug/48h) + p-Phenylenediamine (65 ug/48h)CutaneousSmartPractice Denmark ApS2012-03-01Not applicableUs

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This 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.
Kingdom
Organic compounds
Super Class
Phenylpropanoids and polyketides
Class
Cinnamaldehydes
Sub Class
Not Available
Direct Parent
Cinnamaldehydes
Alternative Parents
Styrenes / Enals / Organic oxides / Hydrocarbon derivatives / Aldehydes
Substituents
Aldehyde / Alpha,beta-unsaturated aldehyde / Aromatic homomonocyclic compound / Benzenoid / Carbonyl group / Cinnamaldehyde / Enal / Hydrocarbon derivative / Monocyclic benzene moiety / Organic oxide
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
cinnamaldehydes (CHEBI:16731) / Monolignols (C00903)

Chemical Identifiers

UNII
SR60A3XG0F
CAS number
14371-10-9
InChI Key
KJPRLNWUNMBNBZ-QPJJXVBHSA-N
InChI
InChI=1S/C9H8O/c10-8-4-7-9-5-2-1-3-6-9/h1-8H/b7-4+
IUPAC Name
(2E)-3-phenylprop-2-enal
SMILES
O=C\C=C\C1=CC=CC=C1

References

General References
  1. Belsito D, Bickers D, Bruze M, Calow P, Greim H, Hanifin JM, Rogers AE, Saurat JH, Sipes IG, Tagami H: A toxicologic and dermatologic assessment of related esters and alcohols of cinnamic acid and cinnamyl alcohol when used as fragrance ingredients. Food Chem Toxicol. 2007;45 Suppl 1:S1-23. doi: 10.1016/j.fct.2007.09.087. Epub 2007 Sep 18. [PubMed:18035463]
Human Metabolome Database
HMDB0003441
KEGG Compound
C00903
ChemSpider
553117
BindingDB
50203065
RxNav
1368153
ChEBI
16731
ChEMBL
CHEMBL293492
ZINC
ZINC000001532777
PDBe Ligand
9Y6
Wikipedia
Cinnamaldehyde
PDB Entries
6agn

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
Not AvailableRecruitingBasic ScienceDermatology/Skin - Other / Pain / Pain, Neuropathic / Pruritus1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
Prices
Not Available
Patents
Not Available

Properties

State
Not Available
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.409 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 FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - GC-MSGC-MSsplash10-0059-3900000000-52db83b595237437ab08
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - EI-BGC-MSsplash10-0f89-5900000000-540c43f6893b35e8a105
GC-MS Spectrum - EI-BGC-MSsplash10-0f89-5900000000-482f8b5c30c53689d8eb
GC-MS Spectrum - EI-BGC-MSsplash10-001i-3900000000-9d274f5e3981ab662650
GC-MS Spectrum - EI-BGC-MSsplash10-001i-0900000000-4f0ad7748ac21b7320c9
GC-MS Spectrum - EI-BGC-MSsplash10-0f89-6900000000-ecaba4b9d657020c3f4c
GC-MS Spectrum - CI-BGC-MSsplash10-001i-0900000000-c02b7869dea8f1113cb4
GC-MS Spectrum - EI-BGC-MSsplash10-001i-2900000000-d89aa99ef7a6ae16b942
GC-MS Spectrum - EI-BGC-MSsplash10-0ugi-8900000000-14f14e29c81360ebdd4b
GC-MS Spectrum - GC-MSGC-MSsplash10-0059-3900000000-52db83b595237437ab08
MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)LC-MS/MSsplash10-0a59-5900000000-a125425df0f09bb01129
MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)LC-MS/MSsplash10-056r-9300000000-043ea317ed08a1cbacfb
MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)LC-MS/MSsplash10-004i-9000000000-39ab07ef5d737e851671
MS/MS Spectrum - EI-B (HITACHI RMU-7M) , PositiveLC-MS/MSsplash10-0f89-5900000000-f27dd11a8900d729bd19
MS/MS Spectrum - EI-B (JEOL JMS-D-3000) , PositiveLC-MS/MSsplash10-0f89-5900000000-4e11cf955911f9ca7da2
MS/MS Spectrum - EI-B (SHIMADZU QP-1000) , PositiveLC-MS/MSsplash10-001i-3900000000-9d274f5e3981ab662650
MS/MS Spectrum - EI-B (SHIMADZU QP-1000) , PositiveLC-MS/MSsplash10-001i-0900000000-4f0ad7748ac21b7320c9
MS/MS Spectrum - EI-B (HITACHI RMU-6M) , PositiveLC-MS/MSsplash10-0f89-6900000000-e363e674a4ec6e092f26
MS/MS Spectrum - CI-B (HITACHI M-80) , PositiveLC-MS/MSsplash10-001i-0900000000-c02b7869dea8f1113cb4
MS/MS Spectrum - EI-B (HITACHI RMU-6M) , PositiveLC-MS/MSsplash10-001i-2900000000-7339e3ff66ab63ba3409
MS/MS Spectrum - EI-B (HITACHI M-80B) , PositiveLC-MS/MSsplash10-0ugi-8900000000-1b72d0d216af15365444
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , PositiveLC-MS/MSsplash10-067i-2900000000-76d2db81f3822a698f0a
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-067i-2900000000-76d2db81f3822a698f0a
1H NMR Spectrum1D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable

Drug created on July 03, 2018 11:24 / Updated on June 12, 2020 10:53

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