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Showing NP-Card for Cinnamaldehyde (NP0000626)

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Record Information
Version1.0
Created at2006-08-12 20:46:08 UTC
Updated at2021-10-07 20:41:02 UTC
NP-MRD IDNP0000626
Secondary Accession NumbersNone
Natural Product 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
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0000626 (Cinnamaldehyde)


  Mrv1652309272007362D          

 10 10  0  0  0  0            999 V2000
10000.004810000.8102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.720510000.3998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.434110000.8102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.149810000.3998    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.290210000.3987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.575810000.8111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.861210000.3986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8612 9999.5736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.5757 9999.1611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.2902 9999.5736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10  5  1  0  0  0  0
  1  5  1  0  0  0  0
M  END
Download

3D MOL for NP0000626 (Cinnamaldehyde)

HMDB0003441
     RDKit          3D
Cinnamaldehyde
 18 18  0  0  0  0  0  0  0  0999 V2000
   -4.3723    1.1333   -0.3388 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5617    0.1906   -0.1895 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1386    0.5195   -0.1177 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3077   -0.4804    0.0386 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1274   -0.2596    0.1217 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9688   -1.3768    0.2900 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3210   -1.1758    0.3690 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8361    0.0997    0.2841 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0154    1.1787    0.1209 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6417    1.0011    0.0381 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9112   -0.8234   -0.1176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8467    1.5494   -0.1952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6796   -1.5168    0.1111 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5539   -2.3601    0.3542 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9801   -2.0196    0.4978 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9264    0.2347    0.3503 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4171    2.2052    0.0516 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0299    1.9001   -0.0926 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10  5  1  0
  2 11  1  0
  3 12  1  0
  4 13  1  0
  6 14  1  0
  7 15  1  0
  8 16  1  0
  9 17  1  0
 10 18  1  0
M  END
Download

3D SDF for NP0000626 (Cinnamaldehyde)


  Mrv1652309272007362D          

 10 10  0  0  0  0            999 V2000
10000.004810000.8102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.720510000.3998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.434110000.8102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.149810000.3998    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.290210000.3987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.575810000.8111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.861210000.3986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8612 9999.5736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.5757 9999.1611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.2902 9999.5736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10  5  1  0  0  0  0
  1  5  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0000626

> <DATABASE_NAME>
NP-MRD

> <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_KEY>
KJPRLNWUNMBNBZ-QPJJXVBHSA-N

> <FORMULA>
C9H8O

> <MOLECULAR_WEIGHT>
132.1592

> <EXACT_MASS>
132.057514878

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
18

> <JCHEM_AVERAGE_POLARIZABILITY>
14.476246951483136

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2E)-3-phenylprop-2-enal

> <ALOGPS_LOGP>
2.00

> <JCHEM_LOGP>
1.9774700076666665

> <ALOGPS_LOGS>
-2.51

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.439447314621728

> <JCHEM_POLAR_SURFACE_AREA>
17.07

> <JCHEM_REFRACTIVITY>
42.1345

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.09e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
cinnamal

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for NP0000626 (Cinnamaldehyde)

HMDB0003441
     RDKit          3D
Cinnamaldehyde
 18 18  0  0  0  0  0  0  0  0999 V2000
   -4.3723    1.1333   -0.3388 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5617    0.1906   -0.1895 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1386    0.5195   -0.1177 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3077   -0.4804    0.0386 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1274   -0.2596    0.1217 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9688   -1.3768    0.2900 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3210   -1.1758    0.3690 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8361    0.0997    0.2841 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0154    1.1787    0.1209 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6417    1.0011    0.0381 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9112   -0.8234   -0.1176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8467    1.5494   -0.1952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6796   -1.5168    0.1111 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5539   -2.3601    0.3542 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9801   -2.0196    0.4978 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9264    0.2347    0.3503 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4171    2.2052    0.0516 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0299    1.9001   -0.0926 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10  5  1  0
  2 11  1  0
  3 12  1  0
  4 13  1  0
  6 14  1  0
  7 15  1  0
  8 16  1  0
  9 17  1  0
 10 18  1  0
M  END
Download

PDB for NP0000626 (Cinnamaldehyde)

HEADER    PROTEIN                                 27-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-20         0                                  
HETATM    1  C   UNK     0    8666.6768668.179   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8668.0128667.413   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8669.3448668.179   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0    8670.6808667.413   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0    8665.3428667.411   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8664.0088668.181   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8662.6748667.411   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8662.6748665.871   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8664.0088665.101   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8665.3428665.871   0.000  0.00  0.00           C+0
CONECT    1    2    5                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3                                                            
CONECT    5    6   10    1                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9    5                                                       
MASTER        0    0    0    0    0    0    0    0   10    0   20    0
END
Download

3D PDB for NP0000626 (Cinnamaldehyde)

COMPND    HMDB0003441
HETATM    1  O1  UNL     1      -4.372   1.133  -0.339  1.00  0.00           O  
HETATM    2  C1  UNL     1      -3.562   0.191  -0.190  1.00  0.00           C  
HETATM    3  C2  UNL     1      -2.139   0.520  -0.118  1.00  0.00           C  
HETATM    4  C3  UNL     1      -1.308  -0.480   0.039  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.127  -0.260   0.122  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.969  -1.377   0.290  1.00  0.00           C  
HETATM    7  C6  UNL     1       2.321  -1.176   0.369  1.00  0.00           C  
HETATM    8  C7  UNL     1       2.836   0.100   0.284  1.00  0.00           C  
HETATM    9  C8  UNL     1       2.015   1.179   0.121  1.00  0.00           C  
HETATM   10  C9  UNL     1       0.642   1.001   0.038  1.00  0.00           C  
HETATM   11  H1  UNL     1      -3.911  -0.823  -0.118  1.00  0.00           H  
HETATM   12  H2  UNL     1      -1.847   1.549  -0.195  1.00  0.00           H  
HETATM   13  H3  UNL     1      -1.680  -1.517   0.111  1.00  0.00           H  
HETATM   14  H4  UNL     1       0.554  -2.360   0.354  1.00  0.00           H  
HETATM   15  H5  UNL     1       2.980  -2.020   0.498  1.00  0.00           H  
HETATM   16  H6  UNL     1       3.926   0.235   0.350  1.00  0.00           H  
HETATM   17  H7  UNL     1       2.417   2.205   0.052  1.00  0.00           H  
HETATM   18  H8  UNL     1       0.030   1.900  -0.093  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   11
CONECT    3    4    4   12
CONECT    4    5   13
CONECT    5    6    6   10
CONECT    6    7   14
CONECT    7    8    8   15
CONECT    8    9   16
CONECT    9   10   10   17
CONECT   10   18
END
Download

SMILES for NP0000626 (Cinnamaldehyde)

O=C\C=C\C1=CC=CC=C1
Download

INCHI for NP0000626 (Cinnamaldehyde)

InChI=1S/C9H8O/c10-8-4-7-9-5-2-1-3-6-9/h1-8H/b7-4+
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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-propenalHMDB
(e)-3-PhenylacroleinHMDB
(e)-3-Phenylprop-2-en-1-alHMDB
(e)-3-Phenylprop-2-enalHMDB
(e)-3-Phenylprop-2-enoneHMDB
e-Cinnamyl aldehydeHMDB
trans-3-PhenylpropenalHMDB
trans-BenzenepropenalHMDB
3-Phenyl-2-propenalHMDB
3-Phenyl-2-propene-1-alHMDB
Chemical FormulaC9H8O
Average Mass132.1592 Da
Monoisotopic Mass132.05751 Da
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 KeyKJPRLNWUNMBNBZ-QPJJXVBHSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CD3OD, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 MHz, Methanol, simulated)Varshavi.d262021-08-09View Spectrum
Species
Species of Origin
Species NameSourceReference
Alpinia chinensisLOTUS Database
Alpinia latilabrisLOTUS Database
Averrhoa carambolaLOTUS Database
Carica papayaKNApSAcK Database
Centaurea benedictaLOTUS Database
Chaerophyllum bulbosumLOTUS Database
Cinnamomum aromaticumKNApSAcK Database
Cinnamomum burmanniLOTUS Database
Cinnamomum cassiaKNApSAcK Database
Cinnamomum japonicumKNApSAcK Database
Cinnamomum osmophloeumLOTUS Database
Cinnamomum tamalaKNApSAcK Database
Cinnamomum verumPlant
Cinnamomum yabunikkeiLOTUS Database
Cinnamomum zeylanicumKNApSAcK Database
Commiphora myrrhaKNApSAcK Database
Commiphora spp.KNApSAcK Database
Cryptocarya amygdalinaLOTUS Database
Cucurbita maximaLOTUS Database
Curcuma xanthorrhizaLOTUS Database
Espeletia timotensisLOTUS Database
Ficus caricaLOTUS Database
Hyacinthus spp.KNApSAcK Database
Ilex paraguariensisKNApSAcK Database
Illicium verumLOTUS Database
Kaempferia galangaLOTUS Database
Lavandula spp.KNApSAcK Database
Litchi chinensisLOTUS Database
Malus sylvestrisLOTUS Database
Mespilodaphne quixosLOTUS Database
Narcissus spp.KNApSAcK Database
Pogostemon cablinKNApSAcK Database
Polygala senegaLOTUS Database
Rhanterium epapposumLOTUS Database
Rhodiola roseaLOTUS Database
Rhodiola rosea L.KNApSAcK Database
Rosa damascenaLOTUS Database
Silene latifoliaPlant
Swertia japonicaLOTUS Database
Syzygium jambosLOTUS Database
Thymus eriocalyxPlant
Thymus X-porlockPlant
Tricholoma matsutakeLOTUS Database
Vachellia rigidulaLOTUS Database
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
Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point-7.5 °CNot Available
Boiling Point248.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility1.42 mg/mL at 25 °CNot Available
LogP1.90Hansch CH, Leo A and Hoekman DH. "Exploring QSAR: Hydrophobic, Electronic, and Steric Constraints. Volume 1" ACS Publications (1995).
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
HMDB IDHMDB0003441
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB030727
KNApSAcK IDC00002725
Chemspider ID553117
KEGG Compound IDC00903
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkCinnamaldehyde
METLIN ID6931
PubChem Compound637511
PDB IDNot Available
ChEBI ID16731
Good Scents IDrw1092691
References
General References
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  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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed:12582388 ]