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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
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
Synthesis and biological evaluation of dimeric cinnamaldehydes as potent antitumor agents.
2006 Apr 15
Delayed occurrence of H-ras12V-induced hepatocellular carcinoma with long-term treatment with cinnamaldehydes.
2006 Jan 20
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
Cinnamoyl-based Nrf2-activators targeting human skin cell photo-oxidative stress.
2008 Aug 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
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
Comparative DNA microarray analysis of human monocyte derived dendritic cells and MUTZ-3 cells exposed to the moderate skin sensitizer cinnamaldehyde.
2009 Sep 15
Influence of cinnamaldehyde on viral myocarditis in mice.
2010 Aug
Involvement of TRPA1 in ET-1-induced pain-like behavior in mice.
2010 Feb 17
Identification of PDL-1 as a novel biomarker of sensitizer exposure in dendritic-like cells.
2010 Sep
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
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
Preferential activation of the vagal nodose nociceptive subtype by TRPA1 agonists in the guinea pig esophagus.
2011 Oct
Spice oil cinnamaldehyde exhibits potent anticandidal activity against fluconazole resistant clinical isolates.
2011 Oct
Effect of cigarette smoking on cough reflex induced by TRPV1 and TRPA1 stimulations.
2012 Mar
Transient receptor potential ankyrin 1 activation enhances hapten sensitization in a T-helper type 2-driven fluorescein isothiocyanate-induced contact hypersensitivity mouse model.
2012 Nov 1
Development of a new in vitro skin sensitization assay (Epidermal Sensitization Assay; EpiSensA) using reconstructed human epidermis.
2013 Dec
Allergic skin inflammation induced by chemical sensitizers is controlled by the transcription factor Nrf2.
2013 Jul
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
PRIVACY ACT
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
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