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Details

Stereochemistry ACHIRAL
Molecular Formula C9H8O
Molecular Weight 132.1592
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of CINNAMALDEHYDE

SMILES

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

InChI

InChIKey=KJPRLNWUNMBNBZ-QPJJXVBHSA-N
InChI=1S/C9H8O/c10-8-4-7-9-5-2-1-3-6-9/h1-8H/b7-4+

HIDE SMILES / InChI
Molecular Formula C9H8O
Molecular Weight 132.1592
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

Description

Cinnamaldehyde is one of the active compounds found in cinnamon. It was reported that cinnamaldehyde has anti-diabetic, anti-cancer, antimicrobial and anti-inflammatiry activity. Cinnamon is a common prescription compound in traditional Chinese medicine and it is used as a dietary supplement all over the world. Cinnamon dietary supplement Cinnamonforce (min. 35% cinnamaldehyde) was tested in phase II clinical trials and demonstrated therapeutic activity in patients with type 2 diabetes. The mechanism of cinnamaldehyde possibly involves the activation of PPAR gamma/delta receptors. Cinnamaldehyde is partially metabolized into cinnamic acid in the stomach and small intestine, and is almost completely metabolized into cinnamic acid in the liver. Cinnamic acid is believed to be the active metabolite, which is responsible for anti-diabetic properties of cinnamaldehyde.

Approval Year

1990
111
Targets

Targets

Primary TargetPharmacologyConditionPotency
Peroxisome proliferator-activated receptor gamma
118
Target ID: P37231|||Q15179
Gene ID: 5468.0
Gene Symbol: PPARG
Target Organism: Homo sapiens (Human)
Agonist
2752
Peroxisome proliferator-activated receptor delta
30
Target ID: Q03181|||Q9BUD4
Gene ID: 5467.0
Gene Symbol: PPARD
Target Organism: Homo sapiens (Human)
Agonist
2752
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Phase II
1147
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Development of a new in vitro skin sensitization assay (Epidermal Sensitization Assay; EpiSensA) using reconstructed human epidermis.
2013-12
Comparative study of the possible protective effects of cinnamic acid and cinnamaldehyde on cisplatin-induced nephrotoxicity in rats.
2013-12
Small molecules inhibit growth, viability and ergosterol biosynthesis in Candida albicans.
2013-12
Evaluation of selected biomarkers for the detection of chemical sensitization in human skin: a comparative study applying THP-1, MUTZ-3 and primary dendritic cells in culture.
2013-09
Allergic skin inflammation induced by chemical sensitizers is controlled by the transcription factor Nrf2.
2013-07
TRP and ASIC channels mediate the antinociceptive effect of citronellyl acetate.
2013-05-25
NCTC 2544 and IL-18 production: a tool for the identification of contact allergens.
2013-04
Transient receptor potential ankyrin 1 activation enhances hapten sensitization in a T-helper type 2-driven fluorescein isothiocyanate-induced contact hypersensitivity mouse model.
2012-11-01
Analysis of transient receptor potential ankyrin 1 (TRPA1) in frogs and lizards illuminates both nociceptive heat and chemical sensitivities and coexpression with TRP vanilloid 1 (TRPV1) in ancestral vertebrates.
2012-08-31
TRPA1 is functionally expressed in melanoma cells but is not critical for impaired proliferation caused by allyl isothiocyanate or cinnamaldehyde.
2012-06
Reduction of Salmonella enterica serovar enteritidis colonization in 20-day-old broiler chickens by the plant-derived compounds trans-cinnamaldehyde and eugenol.
2012-04
Effect of cigarette smoking on cough reflex induced by TRPV1 and TRPA1 stimulations.
2012-03
Methylglyoxal activates the human transient receptor potential ankyrin 1 channel.
2012
In vitro antifungal, anti-elastase and anti-keratinase activity of essential oils of Cinnamomum-, Syzygium- and Cymbopogon-species against Aspergillus fumigatus and Trichophyton rubrum.
2011-12-15
An in vitro test to screen skin sensitizers using a stable THP-1-derived IL-8 reporter cell line, THP-G8.
2011-12
Relating skin sensitizing potency to chemical reactivity: reactive Michael acceptors inhibit NF-κB signaling and are less sensitizing than S(N)Ar- and S(N)2- reactive chemicals.
2011-11-21
TRPV1 and TRPA1 stimulation induces MUC5B secretion in the human nasal airway in vivo.
2011-11
Contact sensitizers modulate the arachidonic acid metabolism of PMA-differentiated U-937 monocytic cells activated by LPS.
2011-10-01
Preferential activation of the vagal nodose nociceptive subtype by TRPA1 agonists in the guinea pig esophagus.
2011-10
Spice oil cinnamaldehyde exhibits potent anticandidal activity against fluconazole resistant clinical isolates.
2011-10
Sensitivity of bronchopulmonary receptors to cold and heat mediated by transient receptor potential cation channel subtypes in an ex vivo rat lung preparation.
2011-08-15
Transient receptor potential ankyrin 1 is expressed by inhibitory motoneurons of the mouse intestine.
2011-08
A novel human volunteer pain model using contact heat evoked potentials (CHEP) following topical skin application of transient receptor potential agonists capsaicin, menthol and cinnamaldehyde.
2011-07
The involvement of TRPA1 channel activation in the inflammatory response evoked by topical application of cinnamaldehyde to mice.
2011-06-20
[Mechanism of cinnamic aldehyde-inducing apoptosis of chronic myeloid leukemic cells in vitro].
2011-06
Antifungal activity of redox-active benzaldehydes that target cellular antioxidation.
2011-05-31
Cinnamaldehyde enhances Nrf2 nuclear translocation to upregulate phase II detoxifying enzyme expression in HepG2 cells.
2011-05-11
Isopentenyl pyrophosphate is a novel antinociceptive substance that inhibits TRPV3 and TRPA1 ion channels.
2011-05
Antifungal activity of essential oils and their synergy with fluconazole against drug-resistant strains of Aspergillus fumigatus and Trichophyton rubrum.
2011-05
Cinnamaldehyde prevents adipocyte differentiation and adipogenesis via regulation of peroxisome proliferator-activated receptor-γ (PPARγ) and AMP-activated protein kinase (AMPK) pathways.
2011-04-27
Human dental pulp fibroblasts express the "cold-sensing" transient receptor potential channels TRPA1 and TRPM8.
2011-04
The intra- and inter-laboratory reproducibility and predictivity of the KeratinoSens assay to predict skin sensitizers in vitro: results of a ring-study in five laboratories.
2011-04
Allyl isothiocyanates and cinnamaldehyde potentiate miniature excitatory postsynaptic inputs in the supraoptic nucleus in rats.
2011-03-25
Effects of cinnamaldehyde on the glucose transport activity of GLUT1.
2011-02
Structure-activity relationship of cinnamaldehyde analogs as inhibitors of AI-2 based quorum sensing and their effect on virulence of Vibrio spp.
2011-01-13
Acetaminophen, via its reactive metabolite N-acetyl-p-benzo-quinoneimine and transient receptor potential ankyrin-1 stimulation, causes neurogenic inflammation in the airways and other tissues in rodents.
2010-12
Prediction of the contact sensitizing potential of chemicals using analysis of gene expression changes in human THP-1 monocytes.
2010-11-10
Evidence for the pathophysiological relevance of TRPA1 receptors in the cardiovascular system in vivo.
2010-09-01
Identification of PDL-1 as a novel biomarker of sensitizer exposure in dendritic-like cells.
2010-09
Influence of cinnamaldehyde on viral myocarditis in mice.
2010-08
Gene markers in dendritic cells unravel pieces of the skin sensitization puzzle.
2010-07-01
The glutaredoxin/glutathione system modulates NF-kappaB activity by glutathionylation of p65 in cinnamaldehyde-treated endothelial cells.
2010-07
Insulinotropic effect of cinnamaldehyde on transcriptional regulation of pyruvate kinase, phosphoenolpyruvate carboxykinase, and GLUT4 translocation in experimental diabetic rats.
2010-06-07
TRPA1-expressing primary afferents synapse with a morphologically identified subclass of substantia gelatinosa neurons in the adult rat spinal cord.
2010-06
Cinnamaldehyde impairs high glucose-induced hypertrophy in renal interstitial fibroblasts.
2010-04-15
Behavioral evidence of thermal hyperalgesia and mechanical allodynia induced by intradermal cinnamaldehyde in rats.
2010-04-12
Cinnamaldehyde up-regulates the mRNA expression level of TRPV1 receptor potential ion channel protein and its function in primary rat DRG neurons in vitro.
2010-01
Regulatory effect of cinnamaldehyde on monocyte/macrophage-mediated inflammatory responses.
2010
High-resolution transcriptional profiling of chemical-stimulated dendritic cells identifies immunogenic contact allergens, but not prohaptens.
2010
Tacrolimus modulates dendritic cell activation in the sensitization phase of allergic contact dermatitis.
2010
Patents

Patents

06627629
9
07902196
1
JP2000026260A
15
JP2000088270A
1
JP2000327566A
1
JP2000355696A
4
JP2002317155A
1
JP2002543059A
1
JP2003535987A
14
JP2007308401A
1
JP2008513896A
12
JP2008542363A
1
JP2009519467A
53
JP2010013487A
1
JP4722396B2
1
JP4723239B2
1
JPH02295906A
2
JPH023661A
1
JPH0374306A
1
JPH037554A
1
JPH06312916A
1
JPH0710704A
1
JPH07289575A
2
JPH10262629A
1
JPH107503A
1
JPH1087456A
2
JPS54132544A
5
JPS59184219A
1
JPS63182326A
1

Sample Use Guides

In Vivo Use Guide
Cinnamonforce (each capsule contains 47 mg of hydroethanolic extract (min. 8% total phenolics) and 23 mg supercritical extract (min. 35% cinnamaldehyde)) is administered at a dose of 140 mg twice daily at the end of each of the two largest meals of the day for 3 months.
Route of Administration: Oral
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Mon Mar 31 17:56:48 GMT 2025
Edited
by admin
on Mon Mar 31 17:56:48 GMT 2025
Record UNII
SR60A3XG0F
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CINNAMALDEHYDE
FCC   FHFI   HSDB   II   MI   WHO-DD  
Systematic Name English
CINNAMAL
INCI  
INCI  
Preferred Name English
Cinnamaldehyde [WHO-DD]
Common Name English
2-PROPENAL, 3-PHENYL-
Systematic Name English
(2E)-3-PHENYLPROP-2-ENAL
Systematic Name English
TRANS-CINNAMALDEHYDE (CONSTITUENT OF CINNAMOMUM CASSIA BARK) [DSC]
Common Name English
CINNAMALDEHYDE [HSDB]
Common Name English
3-PHENYL-2-PROPENAL
Systematic Name English
FEMA NO. 2286
Code English
CINNAMALDEHYDE [FCC]
Common Name English
(E)-3-PHENYL-2-PROPENAL
Systematic Name English
ABION CA
Common Name English
NSC-40346
Code English
CINNAMALDEHYDE [USP-RS]
Common Name English
3-PHENYLACRYLALDEHYDE
Systematic Name English
.BETA.-PHENYLACROLEIN
Common Name English
CINNAMALDEHYDE, TRANS-
Systematic Name English
CINNAMALDEHYDE [II]
Common Name English
CINNAMALDEHYDE (CONSTITUENT OF CINNAMOMUM VERUM BARK) [DSC]
Common Name English
CINNAMALDEHYDE [MI]
Common Name English
NSC-16935
Code English
CINNAMIC ALDEHYDE
Common Name English
CINNAMALDEHYDE [FHFI]
Common Name English
ZIMTALDEHYDE
Common Name English
XC-800
Code English
TRANS-CINNAMALDEHYDE
Systematic Name English
Classification Tree Code System Code
NDF-RT N0000185508
Created by admin on Mon Mar 31 17:56:48 GMT 2025 , Edited by admin on Mon Mar 31 17:56:48 GMT 2025
JECFA EVALUATION CINNAMALDEHYDE
Created by admin on Mon Mar 31 17:56:48 GMT 2025 , Edited by admin on Mon Mar 31 17:56:48 GMT 2025
DSLD 4144 (Number of products:6)
Created by admin on Mon Mar 31 17:56:48 GMT 2025 , Edited by admin on Mon Mar 31 17:56:48 GMT 2025
EC SCIENTIFIC COMMITTEE ON CONSUMER SAFETY OPINION SCCS/1459/11
Created by admin on Mon Mar 31 17:56:48 GMT 2025 , Edited by admin on Mon Mar 31 17:56:48 GMT 2025
Code System Code Type Description
NSC
16935
Created by admin on Mon Mar 31 17:56:48 GMT 2025 , Edited by admin on Mon Mar 31 17:56:48 GMT 2025
PRIMARY
NDF-RT
N0000171131
Created by admin on Mon Mar 31 17:56:48 GMT 2025 , Edited by admin on Mon Mar 31 17:56:48 GMT 2025
PRIMARY Allergens [Chemical/Ingredient]
HSDB
104-55-2
Created by admin on Mon Mar 31 17:56:48 GMT 2025 , Edited by admin on Mon Mar 31 17:56:48 GMT 2025
PRIMARY
FDA UNII
SR60A3XG0F
Created by admin on Mon Mar 31 17:56:48 GMT 2025 , Edited by admin on Mon Mar 31 17:56:48 GMT 2025
PRIMARY
EPA CompTox
DTXSID6024834
Created by admin on Mon Mar 31 17:56:48 GMT 2025 , Edited by admin on Mon Mar 31 17:56:48 GMT 2025
PRIMARY
MESH
C012843
Created by admin on Mon Mar 31 17:56:48 GMT 2025 , Edited by admin on Mon Mar 31 17:56:48 GMT 2025
PRIMARY
NDF-RT
N0000184306
Created by admin on Mon Mar 31 17:56:48 GMT 2025 , Edited by admin on Mon Mar 31 17:56:48 GMT 2025
PRIMARY Cell-mediated Immunity [PE]
EVMPD
SUB37595
Created by admin on Mon Mar 31 17:56:48 GMT 2025 , Edited by admin on Mon Mar 31 17:56:48 GMT 2025
PRIMARY
DRUG BANK
DB14184
Created by admin on Mon Mar 31 17:56:48 GMT 2025 , Edited by admin on Mon Mar 31 17:56:48 GMT 2025
PRIMARY
ECHA (EC/EINECS)
203-213-9
Created by admin on Mon Mar 31 17:56:48 GMT 2025 , Edited by admin on Mon Mar 31 17:56:48 GMT 2025
PRIMARY
MERCK INDEX
m3568
Created by admin on Mon Mar 31 17:56:48 GMT 2025 , Edited by admin on Mon Mar 31 17:56:48 GMT 2025
PRIMARY Merck Index
CAS
14371-10-9
Created by admin on Mon Mar 31 17:56:48 GMT 2025 , Edited by admin on Mon Mar 31 17:56:48 GMT 2025
PRIMARY
NCI_THESAURUS
C76703
Created by admin on Mon Mar 31 17:56:48 GMT 2025 , Edited by admin on Mon Mar 31 17:56:48 GMT 2025
PRIMARY
RS_ITEM_NUM
1133897
Created by admin on Mon Mar 31 17:56:48 GMT 2025 , Edited by admin on Mon Mar 31 17:56:48 GMT 2025
PRIMARY
WIKIPEDIA
CINNAMALDEHYDE
Created by admin on Mon Mar 31 17:56:48 GMT 2025 , Edited by admin on Mon Mar 31 17:56:48 GMT 2025
PRIMARY
CHEBI
142921
Created by admin on Mon Mar 31 17:56:48 GMT 2025 , Edited by admin on Mon Mar 31 17:56:48 GMT 2025
PRIMARY
CAS
104-55-2
Created by admin on Mon Mar 31 17:56:48 GMT 2025 , Edited by admin on Mon Mar 31 17:56:48 GMT 2025
NON-SPECIFIC STEREOCHEMISTRY
ChEMBL
CHEMBL293492
Created by admin on Mon Mar 31 17:56:48 GMT 2025 , Edited by admin on Mon Mar 31 17:56:48 GMT 2025
PRIMARY
DAILYMED
SR60A3XG0F
Created by admin on Mon Mar 31 17:56:48 GMT 2025 , Edited by admin on Mon Mar 31 17:56:48 GMT 2025
PRIMARY
NCI_THESAURUS
C45678
Created by admin on Mon Mar 31 17:56:48 GMT 2025 , Edited by admin on Mon Mar 31 17:56:48 GMT 2025
CONCEPT Industrial Aid
CHEBI
16731
Created by admin on Mon Mar 31 17:56:48 GMT 2025 , Edited by admin on Mon Mar 31 17:56:48 GMT 2025
PRIMARY
NDF-RT
N0000175629
Created by admin on Mon Mar 31 17:56:48 GMT 2025 , Edited by admin on Mon Mar 31 17:56:48 GMT 2025
PRIMARY Increased Histamine Release [PE]
NSC
40346
Created by admin on Mon Mar 31 17:56:48 GMT 2025 , Edited by admin on Mon Mar 31 17:56:48 GMT 2025
PRIMARY
SMS_ID
100000129171
Created by admin on Mon Mar 31 17:56:48 GMT 2025 , Edited by admin on Mon Mar 31 17:56:48 GMT 2025
PRIMARY
RXCUI
1368153
Created by admin on Mon Mar 31 17:56:48 GMT 2025 , Edited by admin on Mon Mar 31 17:56:48 GMT 2025
PRIMARY RxNorm
JECFA MONOGRAPH
692
Created by admin on Mon Mar 31 17:56:48 GMT 2025 , Edited by admin on Mon Mar 31 17:56:48 GMT 2025
PRIMARY
PUBCHEM
637511
Created by admin on Mon Mar 31 17:56:48 GMT 2025 , Edited by admin on Mon Mar 31 17:56:48 GMT 2025
PRIMARY
Related Record Type Details
CINNAMON
PARENT -> CONSTITUENT ALWAYS PRESENT
CINNAMON BARK OIL
PARENT -> CONSTITUENT ALWAYS PRESENT
ASSAY (GC)
CINNAMOMUM CASSIA TWIG
PARENT -> CONSTITUENT ALWAYS PRESENT
CHINESE CINNAMON
PARENT -> CONSTITUENT ALWAYS PRESENT
The irritant and sensitizing properties of cassia oilhave been attributed to cinnamaldehyde.Cinnamaldehyde in toothpastes and perfumes has also been reported to cause contact sensitivity.
CINNAMON LEAF OIL
PARENT -> CONSTITUENT MAY BE PRESENT
CHINESE CINNAMON LEAF OIL
PARENT -> CONSTITUENT ALWAYS PRESENT
TRANSIENT RECEPTOR POTENTIAL CATION CHANNEL SUBFAMILY A MEMBER 1
TARGET -> AGONIST
Related Record Type Details
Structure of CINNAMALDEHYDE
ACTIVE MOIETY
NIH
NCATS
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ACCESSIBILITY
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