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Details

Stereochemistry ACHIRAL
Molecular Formula C9H8O
Molecular Weight 132.1596
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of CINNAMALDEHYDE

SMILES

c1ccc(cc1)/C(/[H])=C(\[H])/C=O

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 132.1596
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

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

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P37231|||Q15179
Gene ID: 5468.0
Gene Symbol: PPARG
Target Organism: Homo sapiens (Human)
Target ID: Q03181|||Q9BUD4
Gene ID: 5467.0
Gene Symbol: PPARD
Target Organism: Homo sapiens (Human)
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Sensitization of TRPA1 by PAR2 contributes to the sensation of inflammatory pain.
2007 Jul
2-hydroxycinnamaldehyde inhibits SW620 colon cancer cell growth through AP-1 inactivation.
2007 May
Transient receptor potential channel A1 involved in sensory transduction of rat urinary bladder through C-fiber pathway.
2007 Oct
Effects of 3-phenyl-propenal on the expression of toll-like receptors and downstream signaling components on raw264.7 murine macrophages.
2008
Cinnamoyl-based Nrf2-activators targeting human skin cell photo-oxidative stress.
2008 Aug 15
Effects of TRPA1 agonists mustard oil and cinnamaldehyde on lumbar spinal wide-dynamic range neuronal responses to innocuous and noxious cutaneous stimuli in rats.
2008 Feb
Cinnamaldehyde inhibits pro-inflammatory cytokines secretion from monocytes/macrophages through suppression of intracellular signaling.
2008 Jan
Modulation of oral heat and cold pain by irritant chemicals.
2008 Jan
Cinnamaldehyde suppresses toll-like receptor 4 activation mediated through the inhibition of receptor oligomerization.
2008 Jan 15
Cross-desensitization of responses of rat trigeminal subnucleus caudalis neurons to cinnamaldehyde and menthol.
2008 Jan 3
Cinnamaldehyde inhibits the tumor necrosis factor-alpha-induced expression of cell adhesion molecules in endothelial cells by suppressing NF-kappaB activation: effects upon IkappaB and Nrf2.
2008 Jun 1
Role of p38 MAPK in the selective release of IL-8 induced by chemical allergen in naive THp-1 cells.
2008 Mar
Effects of cinnamaldehyde on PGE2 release and TRPV4 expression in mouse cerebral microvascular endothelial cells induced by interleukin-1beta.
2008 Mar
Anti-diabetic effects of cinnamaldehyde and berberine and their impacts on retinol-binding protein 4 expression in rats with type 2 diabetes mellitus.
2008 Nov 5
TRPA1 agonists--allyl isothiocyanate and cinnamaldehyde--induce adrenaline secretion.
2008 Oct
HMOX1 and NQO1 genes are upregulated in response to contact sensitizers in dendritic cells and THP-1 cell line: role of the Keap1/Nrf2 pathway.
2009 Feb
The cinnamon-derived Michael acceptor cinnamic aldehyde impairs melanoma cell proliferation, invasiveness, and tumor growth.
2009 Jan 15
Carvacrol is a novel inhibitor of Drosophila TRPL and mammalian TRPM7 channels.
2009 Mar
TRPV1-mediated itch in seasonal allergic rhinitis.
2009 May
QGP-1 cells release 5-HT via TRPA1 activation; a model of human enterochromaffin cells.
2009 Nov
A plasmacytoid dendritic cell (CD123+/CD11c-) based assay system to predict contact allergenicity of chemicals.
2009 Oct 1
Regulatory effect of cinnamaldehyde on monocyte/macrophage-mediated inflammatory responses.
2010
Tacrolimus modulates dendritic cell activation in the sensitization phase of allergic contact dermatitis.
2010
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 Dec
Differential effects of substance P or hemokinin-1 on transient receptor potential channels, TRPV1, TRPA1 and TRPM8, in the rat.
2010 Feb
Involvement of TRPA1 in ET-1-induced pain-like behavior in mice.
2010 Feb 17
TRPA1-expressing primary afferents synapse with a morphologically identified subclass of substantia gelatinosa neurons in the adult rat spinal cord.
2010 Jun
Comparison of a novel CXCL12/CCL5 dependent migration assay with CXCL8 secretion and CD86 expression for distinguishing sensitizers from non-sensitizers using MUTZ-3 Langerhans cells.
2010 Mar
Prediction of the contact sensitizing potential of chemicals using analysis of gene expression changes in human THP-1 monocytes.
2010 Nov 10
Identification of PDL-1 as a novel biomarker of sensitizer exposure in dendritic-like cells.
2010 Sep
Evidence for the pathophysiological relevance of TRPA1 receptors in the cardiovascular system in vivo.
2010 Sep 1
Human dental pulp fibroblasts express the "cold-sensing" transient receptor potential channels TRPA1 and TRPM8.
2011 Apr
Sensitivity of bronchopulmonary receptors to cold and heat mediated by transient receptor potential cation channel subtypes in an ex vivo rat lung preparation.
2011 Aug 15
Effects of cinnamaldehyde on the glucose transport activity of GLUT1.
2011 Feb
Structure-activity relationship of cinnamaldehyde analogs as inhibitors of AI-2 based quorum sensing and their effect on virulence of Vibrio spp.
2011 Jan 13
The involvement of TRPA1 channel activation in the inflammatory response evoked by topical application of cinnamaldehyde to mice.
2011 Jun 20
Allyl isothiocyanates and cinnamaldehyde potentiate miniature excitatory postsynaptic inputs in the supraoptic nucleus in rats.
2011 Mar 25
Antifungal activity of essential oils and their synergy with fluconazole against drug-resistant strains of Aspergillus fumigatus and Trichophyton rubrum.
2011 May
Cinnamaldehyde enhances Nrf2 nuclear translocation to upregulate phase II detoxifying enzyme expression in HepG2 cells.
2011 May 11
TRPV1 and TRPA1 stimulation induces MUC5B secretion in the human nasal airway in vivo.
2011 Nov
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 Nov 21
Spice oil cinnamaldehyde exhibits potent anticandidal activity against fluconazole resistant clinical isolates.
2011 Oct
Methylglyoxal activates the human transient receptor potential ankyrin 1 channel.
2012
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 Aug 31
Effect of cigarette smoking on cough reflex induced by TRPV1 and TRPA1 stimulations.
2012 Mar
NCTC 2544 and IL-18 production: a tool for the identification of contact allergens.
2013 Apr
Development of a new in vitro skin sensitization assay (Epidermal Sensitization Assay; EpiSensA) using reconstructed human epidermis.
2013 Dec
Comparative study of the possible protective effects of cinnamic acid and cinnamaldehyde on cisplatin-induced nephrotoxicity in rats.
2013 Dec
Allergic skin inflammation induced by chemical sensitizers is controlled by the transcription factor Nrf2.
2013 Jul
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 Sep
Patents

Sample Use Guides

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 Sat Jun 26 09:40:34 UTC 2021
Edited
by admin
on Sat Jun 26 09:40:34 UTC 2021
Record UNII
SR60A3XG0F
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CINNAMALDEHYDE
FCC   FHFI   HSDB   II   MI   WHO-DD  
Systematic Name English
2-PROPENAL, 3-PHENYL-
Systematic Name English
CINNAMALDEHYDE [WHO-DD]
Common 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
CINNAMAL [INCI]
Common Name 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
CINNAMAL
INCI  
INCI  
Official 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 Sat Jun 26 09:40:34 UTC 2021 , Edited by admin on Sat Jun 26 09:40:34 UTC 2021
JECFA EVALUATION CINNAMALDEHYDE
Created by admin on Sat Jun 26 09:40:34 UTC 2021 , Edited by admin on Sat Jun 26 09:40:34 UTC 2021
DSLD 4144 (Number of products:6)
Created by admin on Sat Jun 26 09:40:34 UTC 2021 , Edited by admin on Sat Jun 26 09:40:34 UTC 2021
EC SCIENTIFIC COMMITTEE ON CONSUMER SAFETY OPINION SCCS/1459/11
Created by admin on Sat Jun 26 09:40:34 UTC 2021 , Edited by admin on Sat Jun 26 09:40:34 UTC 2021
Code System Code Type Description
NDF-RT
N0000171131
Created by admin on Sat Jun 26 09:40:34 UTC 2021 , Edited by admin on Sat Jun 26 09:40:34 UTC 2021
PRIMARY Allergens [Chemical/Ingredient]
HSDB
104-55-2
Created by admin on Sat Jun 26 09:40:34 UTC 2021 , Edited by admin on Sat Jun 26 09:40:34 UTC 2021
PRIMARY
FDA UNII
SR60A3XG0F
Created by admin on Sat Jun 26 09:40:34 UTC 2021 , Edited by admin on Sat Jun 26 09:40:34 UTC 2021
PRIMARY
EPA CompTox
14371-10-9
Created by admin on Sat Jun 26 09:40:34 UTC 2021 , Edited by admin on Sat Jun 26 09:40:34 UTC 2021
PRIMARY
MESH
C012843
Created by admin on Sat Jun 26 09:40:34 UTC 2021 , Edited by admin on Sat Jun 26 09:40:34 UTC 2021
PRIMARY
USP_CATALOG
1133897
Created by admin on Sat Jun 26 09:40:34 UTC 2021 , Edited by admin on Sat Jun 26 09:40:34 UTC 2021
PRIMARY USP-RS
NDF-RT
N0000184306
Created by admin on Sat Jun 26 09:40:34 UTC 2021 , Edited by admin on Sat Jun 26 09:40:34 UTC 2021
PRIMARY Cell-mediated Immunity [PE]
EVMPD
SUB37595
Created by admin on Sat Jun 26 09:40:34 UTC 2021 , Edited by admin on Sat Jun 26 09:40:34 UTC 2021
PRIMARY
DRUG BANK
DB14184
Created by admin on Sat Jun 26 09:40:34 UTC 2021 , Edited by admin on Sat Jun 26 09:40:34 UTC 2021
PRIMARY
ECHA (EC/EINECS)
203-213-9
Created by admin on Sat Jun 26 09:40:34 UTC 2021 , Edited by admin on Sat Jun 26 09:40:34 UTC 2021
PRIMARY
MERCK INDEX
M3568
Created by admin on Sat Jun 26 09:40:34 UTC 2021 , Edited by admin on Sat Jun 26 09:40:34 UTC 2021
PRIMARY Merck Index
CAS
14371-10-9
Created by admin on Sat Jun 26 09:40:34 UTC 2021 , Edited by admin on Sat Jun 26 09:40:34 UTC 2021
PRIMARY
NCI_THESAURUS
C76703
Created by admin on Sat Jun 26 09:40:34 UTC 2021 , Edited by admin on Sat Jun 26 09:40:34 UTC 2021
PRIMARY
WIKIPEDIA
CINNAMALDEHYDE
Created by admin on Sat Jun 26 09:40:34 UTC 2021 , Edited by admin on Sat Jun 26 09:40:34 UTC 2021
PRIMARY
CAS
104-55-2
Created by admin on Sat Jun 26 09:40:34 UTC 2021 , Edited by admin on Sat Jun 26 09:40:34 UTC 2021
NON-SPECIFIC STEREOCHEMISTRY
ChEMBL
CHEMBL293492
Created by admin on Sat Jun 26 09:40:34 UTC 2021 , Edited by admin on Sat Jun 26 09:40:34 UTC 2021
PRIMARY
NCI_THESAURUS
C45678
Created by admin on Sat Jun 26 09:40:34 UTC 2021 , Edited by admin on Sat Jun 26 09:40:34 UTC 2021
CONCEPT Industrial Aid
NDF-RT
N0000175629
Created by admin on Sat Jun 26 09:40:34 UTC 2021 , Edited by admin on Sat Jun 26 09:40:34 UTC 2021
PRIMARY Increased Histamine Release [PE]
RXCUI
1368153
Created by admin on Sat Jun 26 09:40:34 UTC 2021 , Edited by admin on Sat Jun 26 09:40:34 UTC 2021
PRIMARY RxNorm
PUBCHEM
637511
Created by admin on Sat Jun 26 09:40:34 UTC 2021 , Edited by admin on Sat Jun 26 09:40:34 UTC 2021
PRIMARY
Related Record Type Details
PARENT -> CONSTITUENT ALWAYS PRESENT
PARENT -> CONSTITUENT ALWAYS PRESENT
PARENT -> CONSTITUENT ALWAYS PRESENT
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.
PARENT -> CONSTITUENT MAY BE PRESENT
PARENT -> CONSTITUENT ALWAYS PRESENT
TARGET -> AGONIST
Related Record Type Details
ACTIVE MOIETY