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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
105
Targets

Targets

Primary TargetPharmacologyConditionPotency
Peroxisome proliferator-activated receptor gamma
109
Target ID: P37231|||Q15179
Gene ID: 5468.0
Gene Symbol: PPARG
Target Organism: Homo sapiens (Human)
Agonist
2662
Peroxisome proliferator-activated receptor delta
27
Target ID: Q03181|||Q9BUD4
Gene ID: 5467.0
Gene Symbol: PPARD
Target Organism: Homo sapiens (Human)
Agonist
2662
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Phase II
1144
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Human skin absorption and metabolism of the contact allergens, cinnamic aldehyde, and cinnamic alcohol.
2000 Nov 1
Dermal exposure to cinnamaldehyde alters lymphocyte subpopulations, number of interferon-gamma-producing cells, and expression of B7 costimulatory molecules and cytokine messenger RNAs in auricular lymph nodes of B6C3F1 mice.
2001 Mar
Antioxidative function and substrate specificity of NAD(P)H-dependent alkenal/one oxidoreductase. A new role for leukotriene B4 12-hydroxydehydrogenase/15-oxoprostaglandin 13-reductase.
2001 Nov 2
Peptidyl aldehydes as reversible covalent inhibitors of protein tyrosine phosphatases.
2002 Aug 27
Deodorants: an experimental provocation study with cinnamic aldehyde.
2003 Feb
Protein binding and metabolism influence the relative skin sensitization potential of cinnamic compounds.
2004 Mar
Noxious cold ion channel TRPA1 is activated by pungent compounds and bradykinin.
2004 Mar 25
Effects of vitamin E on the cinnamaldehyde-induced apoptotic mechanism in human PLC/PRF/5 cells.
2004 Nov
TRPA1 and TRPM8 activation in humans: effects of cinnamaldehyde and menthol.
2005 Jun 21
Cinnamaldehyde reduction of platelet aggregation and thrombosis in rodents.
2007
Sensitization of TRPA1 by PAR2 contributes to the sensation of inflammatory pain.
2007 Jul
Antimutagenicity of cinnamaldehyde and vanillin in human cells: Global gene expression and possible role of DNA damage and repair.
2007 Mar 1
Effects of 3-phenyl-propenal on the expression of toll-like receptors and downstream signaling components on raw264.7 murine macrophages.
2008
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
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
Role of TRPM8 and TRPA1 for cold allodynia in patients with cold injury.
2008 Sep 30
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
Cinnamaldehyde impairs high glucose-induced hypertrophy in renal interstitial fibroblasts.
2010 Apr 15
Differential effects of substance P or hemokinin-1 on transient receptor potential channels, TRPV1, TRPA1 and TRPM8, in the rat.
2010 Feb
The glutaredoxin/glutathione system modulates NF-kappaB activity by glutathionylation of p65 in cinnamaldehyde-treated endothelial cells.
2010 Jul
Gene markers in dendritic cells unravel pieces of the skin sensitization puzzle.
2010 Jul 1
TRPA1-expressing primary afferents synapse with a morphologically identified subclass of substantia gelatinosa neurons in the adult rat spinal cord.
2010 Jun
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
Cinnamaldehyde prevents adipocyte differentiation and adipogenesis via regulation of peroxisome proliferator-activated receptor-γ (PPARγ) and AMP-activated protein kinase (AMPK) pathways.
2011 Apr 27
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
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 Jul
The involvement of TRPA1 channel activation in the inflammatory response evoked by topical application of cinnamaldehyde to mice.
2011 Jun 20
Isopentenyl pyrophosphate is a novel antinociceptive substance that inhibits TRPV3 and TRPA1 ion channels.
2011 May
Antifungal activity of essential oils and their synergy with fluconazole against drug-resistant strains of Aspergillus fumigatus and Trichophyton rubrum.
2011 May
Effect of cigarette smoking on cough reflex induced by TRPV1 and TRPA1 stimulations.
2012 Mar
Development of a new in vitro skin sensitization assay (Epidermal Sensitization Assay; EpiSensA) using reconstructed human epidermis.
2013 Dec
Small molecules inhibit growth, viability and ergosterol biosynthesis in Candida albicans.
2013 Dec
Patents

Patents

06627629
9
07902196
1
JP2000026260A
13
JP2000088270A
1
JP2000327566A
1
JP2000355696A
4
JP2002317155A
1
JP2002543059A
1
JP2003535987A
14
JP2007308401A
1
JP2008513896A
12
JP2008542363A
1
JP2009519467A
52
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 Wed Jul 05 22:55:04 UTC 2023
Edited
by admin
on Wed Jul 05 22:55:04 UTC 2023
Record UNII
SR60A3XG0F
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CINNAMALDEHYDE
FCC   FHFI   HSDB   II   MI   WHO-DD  
Systematic 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
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 Wed Jul 05 22:55:04 UTC 2023 , Edited by admin on Wed Jul 05 22:55:04 UTC 2023
JECFA EVALUATION CINNAMALDEHYDE
Created by admin on Wed Jul 05 22:55:04 UTC 2023 , Edited by admin on Wed Jul 05 22:55:04 UTC 2023
DSLD 4144 (Number of products:6)
Created by admin on Wed Jul 05 22:55:04 UTC 2023 , Edited by admin on Wed Jul 05 22:55:04 UTC 2023
EC SCIENTIFIC COMMITTEE ON CONSUMER SAFETY OPINION SCCS/1459/11
Created by admin on Wed Jul 05 22:55:04 UTC 2023 , Edited by admin on Wed Jul 05 22:55:04 UTC 2023
Code System Code Type Description
NSC
16935
Created by admin on Wed Jul 05 22:55:04 UTC 2023 , Edited by admin on Wed Jul 05 22:55:04 UTC 2023
PRIMARY
NDF-RT
N0000171131
Created by admin on Wed Jul 05 22:55:04 UTC 2023 , Edited by admin on Wed Jul 05 22:55:04 UTC 2023
PRIMARY Allergens [Chemical/Ingredient]
HSDB
104-55-2
Created by admin on Wed Jul 05 22:55:04 UTC 2023 , Edited by admin on Wed Jul 05 22:55:04 UTC 2023
PRIMARY
FDA UNII
SR60A3XG0F
Created by admin on Wed Jul 05 22:55:04 UTC 2023 , Edited by admin on Wed Jul 05 22:55:04 UTC 2023
PRIMARY
EPA CompTox
DTXSID6024834
Created by admin on Wed Jul 05 22:55:04 UTC 2023 , Edited by admin on Wed Jul 05 22:55:04 UTC 2023
PRIMARY
MESH
C012843
Created by admin on Wed Jul 05 22:55:04 UTC 2023 , Edited by admin on Wed Jul 05 22:55:04 UTC 2023
PRIMARY
NDF-RT
N0000184306
Created by admin on Wed Jul 05 22:55:04 UTC 2023 , Edited by admin on Wed Jul 05 22:55:04 UTC 2023
PRIMARY Cell-mediated Immunity [PE]
EVMPD
SUB37595
Created by admin on Wed Jul 05 22:55:04 UTC 2023 , Edited by admin on Wed Jul 05 22:55:04 UTC 2023
PRIMARY
DRUG BANK
DB14184
Created by admin on Wed Jul 05 22:55:04 UTC 2023 , Edited by admin on Wed Jul 05 22:55:04 UTC 2023
PRIMARY
ECHA (EC/EINECS)
203-213-9
Created by admin on Wed Jul 05 22:55:04 UTC 2023 , Edited by admin on Wed Jul 05 22:55:04 UTC 2023
PRIMARY
MERCK INDEX
M3568
Created by admin on Wed Jul 05 22:55:04 UTC 2023 , Edited by admin on Wed Jul 05 22:55:04 UTC 2023
PRIMARY Merck Index
CAS
14371-10-9
Created by admin on Wed Jul 05 22:55:04 UTC 2023 , Edited by admin on Wed Jul 05 22:55:04 UTC 2023
PRIMARY
NCI_THESAURUS
C76703
Created by admin on Wed Jul 05 22:55:04 UTC 2023 , Edited by admin on Wed Jul 05 22:55:04 UTC 2023
PRIMARY
RS_ITEM_NUM
1133897
Created by admin on Wed Jul 05 22:55:04 UTC 2023 , Edited by admin on Wed Jul 05 22:55:04 UTC 2023
PRIMARY
WIKIPEDIA
CINNAMALDEHYDE
Created by admin on Wed Jul 05 22:55:04 UTC 2023 , Edited by admin on Wed Jul 05 22:55:04 UTC 2023
PRIMARY
CHEBI
142921
Created by admin on Wed Jul 05 22:55:04 UTC 2023 , Edited by admin on Wed Jul 05 22:55:04 UTC 2023
PRIMARY
CAS
104-55-2
Created by admin on Wed Jul 05 22:55:04 UTC 2023 , Edited by admin on Wed Jul 05 22:55:04 UTC 2023
NON-SPECIFIC STEREOCHEMISTRY
ChEMBL
CHEMBL293492
Created by admin on Wed Jul 05 22:55:04 UTC 2023 , Edited by admin on Wed Jul 05 22:55:04 UTC 2023
PRIMARY
DAILYMED
SR60A3XG0F
Created by admin on Wed Jul 05 22:55:04 UTC 2023 , Edited by admin on Wed Jul 05 22:55:04 UTC 2023
PRIMARY
NCI_THESAURUS
C45678
Created by admin on Wed Jul 05 22:55:04 UTC 2023 , Edited by admin on Wed Jul 05 22:55:04 UTC 2023
CONCEPT Industrial Aid
CHEBI
16731
Created by admin on Wed Jul 05 22:55:04 UTC 2023 , Edited by admin on Wed Jul 05 22:55:04 UTC 2023
PRIMARY
NDF-RT
N0000175629
Created by admin on Wed Jul 05 22:55:04 UTC 2023 , Edited by admin on Wed Jul 05 22:55:04 UTC 2023
PRIMARY Increased Histamine Release [PE]
NSC
40346
Created by admin on Wed Jul 05 22:55:04 UTC 2023 , Edited by admin on Wed Jul 05 22:55:04 UTC 2023
PRIMARY
SMS_ID
100000129171
Created by admin on Wed Jul 05 22:55:04 UTC 2023 , Edited by admin on Wed Jul 05 22:55:04 UTC 2023
PRIMARY
RXCUI
1368153
Created by admin on Wed Jul 05 22:55:04 UTC 2023 , Edited by admin on Wed Jul 05 22:55:04 UTC 2023
PRIMARY RxNorm
PUBCHEM
637511
Created by admin on Wed Jul 05 22:55:04 UTC 2023 , Edited by admin on Wed Jul 05 22:55:04 UTC 2023
PRIMARY
Related Record Type Details
CINNAMON
PARENT -> CONSTITUENT ALWAYS PRESENT
CINNAMON BARK OIL
PARENT -> CONSTITUENT ALWAYS PRESENT
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
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