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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
108
Targets

Targets

Primary TargetPharmacologyConditionPotency
Peroxisome proliferator-activated receptor gamma
111
Target ID: P37231|||Q15179
Gene ID: 5468.0
Gene Symbol: PPARG
Target Organism: Homo sapiens (Human)
Agonist
2678
Peroxisome proliferator-activated receptor delta
29
Target ID: Q03181|||Q9BUD4
Gene ID: 5467.0
Gene Symbol: PPARD
Target Organism: Homo sapiens (Human)
Agonist
2678
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Phase II
1132
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Noxious compounds activate TRPA1 ion channels through covalent modification of cysteines.
2007 Feb 1
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
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
Suppression of age-related inflammatory NF-kappaB activation by cinnamaldehyde.
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
Role of TRPM8 and TRPA1 for cold allodynia in patients with cold injury.
2008 Sep 30
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
A plasmacytoid dendritic cell (CD123+/CD11c-) based assay system to predict contact allergenicity of chemicals.
2009 Oct 1
Comparative DNA microarray analysis of human monocyte derived dendritic cells and MUTZ-3 cells exposed to the moderate skin sensitizer cinnamaldehyde.
2009 Sep 15
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
Behavioral evidence of thermal hyperalgesia and mechanical allodynia induced by intradermal cinnamaldehyde in rats.
2010 Apr 12
Cinnamaldehyde impairs high glucose-induced hypertrophy in renal interstitial fibroblasts.
2010 Apr 15
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 Jan
High-throughput gene expression analysis of intestinal intraepithelial lymphocytes after oral feeding of carvacrol, cinnamaldehyde, or Capsicum oleoresin.
2010 Jan
Gene markers in dendritic cells unravel pieces of the skin sensitization puzzle.
2010 Jul 1
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
An in vitro test to screen skin sensitizers using a stable THP-1-derived IL-8 reporter cell line, THP-G8.
2011 Dec
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 Dec 15
Antifungal activity of redox-active benzaldehydes that target cellular antioxidation.
2011 May 31
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
Contact sensitizers modulate the arachidonic acid metabolism of PMA-differentiated U-937 monocytic cells activated by LPS.
2011 Oct 1
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
TRPA1 is functionally expressed in melanoma cells but is not critical for impaired proliferation caused by allyl isothiocyanate or cinnamaldehyde.
2012 Jun
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
Small molecules inhibit growth, viability and ergosterol biosynthesis in Candida albicans.
2013 Dec
Allergic skin inflammation induced by chemical sensitizers is controlled by the transcription factor Nrf2.
2013 Jul
TRP and ASIC channels mediate the antinociceptive effect of citronellyl acetate.
2013 May 25
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

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 Fri Dec 15 15:24:47 GMT 2023
Edited
by admin
on Fri Dec 15 15:24:47 GMT 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 Fri Dec 15 15:24:47 GMT 2023 , Edited by admin on Fri Dec 15 15:24:47 GMT 2023
JECFA EVALUATION CINNAMALDEHYDE
Created by admin on Fri Dec 15 15:24:47 GMT 2023 , Edited by admin on Fri Dec 15 15:24:47 GMT 2023
DSLD 4144 (Number of products:6)
Created by admin on Fri Dec 15 15:24:47 GMT 2023 , Edited by admin on Fri Dec 15 15:24:47 GMT 2023
EC SCIENTIFIC COMMITTEE ON CONSUMER SAFETY OPINION SCCS/1459/11
Created by admin on Fri Dec 15 15:24:47 GMT 2023 , Edited by admin on Fri Dec 15 15:24:47 GMT 2023
Code System Code Type Description
NSC
16935
Created by admin on Fri Dec 15 15:24:47 GMT 2023 , Edited by admin on Fri Dec 15 15:24:47 GMT 2023
PRIMARY
NDF-RT
N0000171131
Created by admin on Fri Dec 15 15:24:47 GMT 2023 , Edited by admin on Fri Dec 15 15:24:47 GMT 2023
PRIMARY Allergens [Chemical/Ingredient]
HSDB
104-55-2
Created by admin on Fri Dec 15 15:24:47 GMT 2023 , Edited by admin on Fri Dec 15 15:24:47 GMT 2023
PRIMARY
FDA UNII
SR60A3XG0F
Created by admin on Fri Dec 15 15:24:47 GMT 2023 , Edited by admin on Fri Dec 15 15:24:47 GMT 2023
PRIMARY
EPA CompTox
DTXSID6024834
Created by admin on Fri Dec 15 15:24:47 GMT 2023 , Edited by admin on Fri Dec 15 15:24:47 GMT 2023
PRIMARY
MESH
C012843
Created by admin on Fri Dec 15 15:24:47 GMT 2023 , Edited by admin on Fri Dec 15 15:24:47 GMT 2023
PRIMARY
NDF-RT
N0000184306
Created by admin on Fri Dec 15 15:24:47 GMT 2023 , Edited by admin on Fri Dec 15 15:24:47 GMT 2023
PRIMARY Cell-mediated Immunity [PE]
EVMPD
SUB37595
Created by admin on Fri Dec 15 15:24:47 GMT 2023 , Edited by admin on Fri Dec 15 15:24:47 GMT 2023
PRIMARY
DRUG BANK
DB14184
Created by admin on Fri Dec 15 15:24:47 GMT 2023 , Edited by admin on Fri Dec 15 15:24:47 GMT 2023
PRIMARY
ECHA (EC/EINECS)
203-213-9
Created by admin on Fri Dec 15 15:24:47 GMT 2023 , Edited by admin on Fri Dec 15 15:24:47 GMT 2023
PRIMARY
MERCK INDEX
m3568
Created by admin on Fri Dec 15 15:24:47 GMT 2023 , Edited by admin on Fri Dec 15 15:24:47 GMT 2023
PRIMARY Merck Index
CAS
14371-10-9
Created by admin on Fri Dec 15 15:24:47 GMT 2023 , Edited by admin on Fri Dec 15 15:24:47 GMT 2023
PRIMARY
NCI_THESAURUS
C76703
Created by admin on Fri Dec 15 15:24:47 GMT 2023 , Edited by admin on Fri Dec 15 15:24:47 GMT 2023
PRIMARY
RS_ITEM_NUM
1133897
Created by admin on Fri Dec 15 15:24:47 GMT 2023 , Edited by admin on Fri Dec 15 15:24:47 GMT 2023
PRIMARY
WIKIPEDIA
CINNAMALDEHYDE
Created by admin on Fri Dec 15 15:24:47 GMT 2023 , Edited by admin on Fri Dec 15 15:24:47 GMT 2023
PRIMARY
CHEBI
142921
Created by admin on Fri Dec 15 15:24:47 GMT 2023 , Edited by admin on Fri Dec 15 15:24:47 GMT 2023
PRIMARY
CAS
104-55-2
Created by admin on Fri Dec 15 15:24:47 GMT 2023 , Edited by admin on Fri Dec 15 15:24:47 GMT 2023
NON-SPECIFIC STEREOCHEMISTRY
ChEMBL
CHEMBL293492
Created by admin on Fri Dec 15 15:24:47 GMT 2023 , Edited by admin on Fri Dec 15 15:24:47 GMT 2023
PRIMARY
DAILYMED
SR60A3XG0F
Created by admin on Fri Dec 15 15:24:47 GMT 2023 , Edited by admin on Fri Dec 15 15:24:47 GMT 2023
PRIMARY
NCI_THESAURUS
C45678
Created by admin on Fri Dec 15 15:24:47 GMT 2023 , Edited by admin on Fri Dec 15 15:24:47 GMT 2023
CONCEPT Industrial Aid
CHEBI
16731
Created by admin on Fri Dec 15 15:24:47 GMT 2023 , Edited by admin on Fri Dec 15 15:24:47 GMT 2023
PRIMARY
NDF-RT
N0000175629
Created by admin on Fri Dec 15 15:24:47 GMT 2023 , Edited by admin on Fri Dec 15 15:24:47 GMT 2023
PRIMARY Increased Histamine Release [PE]
NSC
40346
Created by admin on Fri Dec 15 15:24:47 GMT 2023 , Edited by admin on Fri Dec 15 15:24:47 GMT 2023
PRIMARY
SMS_ID
100000129171
Created by admin on Fri Dec 15 15:24:47 GMT 2023 , Edited by admin on Fri Dec 15 15:24:47 GMT 2023
PRIMARY
RXCUI
1368153
Created by admin on Fri Dec 15 15:24:47 GMT 2023 , Edited by admin on Fri Dec 15 15:24:47 GMT 2023
PRIMARY RxNorm
JECFA MONOGRAPH
692
Created by admin on Fri Dec 15 15:24:47 GMT 2023 , Edited by admin on Fri Dec 15 15:24:47 GMT 2023
PRIMARY
PUBCHEM
637511
Created by admin on Fri Dec 15 15:24:47 GMT 2023 , Edited by admin on Fri Dec 15 15:24:47 GMT 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
NCATS
PRIVACY ACT
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
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