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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
106
Target ID: P37231|||Q15179
Gene ID: 5468.0
Gene Symbol: PPARG
Target Organism: Homo sapiens (Human)
Agonist
2637
Peroxisome proliferator-activated receptor delta
26
Target ID: Q03181|||Q9BUD4
Gene ID: 5467.0
Gene Symbol: PPARD
Target Organism: Homo sapiens (Human)
Agonist
2637
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Phase II
1133
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
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
More than cool: promiscuous relationships of menthol and other sensory compounds.
2006 Aug
Cinnamaldehyde reduces IL-1beta-induced cyclooxygenase-2 activity in rat cerebral microvascular endothelial cells.
2006 May 10
Effects of 3-phenyl-propenal on the expression of toll-like receptors and downstream signaling components on raw264.7 murine macrophages.
2008
Effects of cinnamaldehyde on PGE2 release and TRPV4 expression in mouse cerebral microvascular endothelial cells induced by interleukin-1beta.
2008 Mar
The cinnamon-derived Michael acceptor cinnamic aldehyde impairs melanoma cell proliferation, invasiveness, and tumor growth.
2009 Jan 15
High-resolution transcriptional profiling of chemical-stimulated dendritic cells identifies immunogenic contact allergens, but not prohaptens.
2010
Behavioral evidence of thermal hyperalgesia and mechanical allodynia induced by intradermal cinnamaldehyde in rats.
2010 Apr 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 Jan
Gene markers in dendritic cells unravel pieces of the skin sensitization puzzle.
2010 Jul 1
Evidence for the pathophysiological relevance of TRPA1 receptors in the cardiovascular system in vivo.
2010 Sep 1
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
Transient receptor potential ankyrin 1 is expressed by inhibitory motoneurons of the mouse intestine.
2011 Aug
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
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
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

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
51
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 16 17:02:33 UTC 2022
Edited
by admin
on Fri Dec 16 17:02:33 UTC 2022
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 16 17:02:33 UTC 2022 , Edited by admin on Fri Dec 16 17:02:33 UTC 2022
JECFA EVALUATION CINNAMALDEHYDE
Created by admin on Fri Dec 16 17:02:33 UTC 2022 , Edited by admin on Fri Dec 16 17:02:33 UTC 2022
DSLD 4144 (Number of products:6)
Created by admin on Fri Dec 16 17:02:33 UTC 2022 , Edited by admin on Fri Dec 16 17:02:33 UTC 2022
EC SCIENTIFIC COMMITTEE ON CONSUMER SAFETY OPINION SCCS/1459/11
Created by admin on Fri Dec 16 17:02:33 UTC 2022 , Edited by admin on Fri Dec 16 17:02:33 UTC 2022
Code System Code Type Description
NSC
16935
Created by admin on Fri Dec 16 17:02:33 UTC 2022 , Edited by admin on Fri Dec 16 17:02:33 UTC 2022
PRIMARY
NDF-RT
N0000171131
Created by admin on Fri Dec 16 17:02:33 UTC 2022 , Edited by admin on Fri Dec 16 17:02:33 UTC 2022
PRIMARY Allergens [Chemical/Ingredient]
HSDB
104-55-2
Created by admin on Fri Dec 16 17:02:33 UTC 2022 , Edited by admin on Fri Dec 16 17:02:33 UTC 2022
PRIMARY
FDA UNII
SR60A3XG0F
Created by admin on Fri Dec 16 17:02:33 UTC 2022 , Edited by admin on Fri Dec 16 17:02:33 UTC 2022
PRIMARY
EPA CompTox
DTXSID6024834
Created by admin on Fri Dec 16 17:02:33 UTC 2022 , Edited by admin on Fri Dec 16 17:02:33 UTC 2022
PRIMARY
MESH
C012843
Created by admin on Fri Dec 16 17:02:33 UTC 2022 , Edited by admin on Fri Dec 16 17:02:33 UTC 2022
PRIMARY
NDF-RT
N0000184306
Created by admin on Fri Dec 16 17:02:33 UTC 2022 , Edited by admin on Fri Dec 16 17:02:33 UTC 2022
PRIMARY Cell-mediated Immunity [PE]
EVMPD
SUB37595
Created by admin on Fri Dec 16 17:02:33 UTC 2022 , Edited by admin on Fri Dec 16 17:02:33 UTC 2022
PRIMARY
DRUG BANK
DB14184
Created by admin on Fri Dec 16 17:02:33 UTC 2022 , Edited by admin on Fri Dec 16 17:02:33 UTC 2022
PRIMARY
ECHA (EC/EINECS)
203-213-9
Created by admin on Fri Dec 16 17:02:33 UTC 2022 , Edited by admin on Fri Dec 16 17:02:33 UTC 2022
PRIMARY
MERCK INDEX
M3568
Created by admin on Fri Dec 16 17:02:33 UTC 2022 , Edited by admin on Fri Dec 16 17:02:33 UTC 2022
PRIMARY Merck Index
CAS
14371-10-9
Created by admin on Fri Dec 16 17:02:33 UTC 2022 , Edited by admin on Fri Dec 16 17:02:33 UTC 2022
PRIMARY
NCI_THESAURUS
C76703
Created by admin on Fri Dec 16 17:02:33 UTC 2022 , Edited by admin on Fri Dec 16 17:02:33 UTC 2022
PRIMARY
RS_ITEM_NUM
1133897
Created by admin on Fri Dec 16 17:02:33 UTC 2022 , Edited by admin on Fri Dec 16 17:02:33 UTC 2022
PRIMARY
WIKIPEDIA
CINNAMALDEHYDE
Created by admin on Fri Dec 16 17:02:33 UTC 2022 , Edited by admin on Fri Dec 16 17:02:33 UTC 2022
PRIMARY
CHEBI
142921
Created by admin on Fri Dec 16 17:02:33 UTC 2022 , Edited by admin on Fri Dec 16 17:02:33 UTC 2022
PRIMARY
CAS
104-55-2
Created by admin on Fri Dec 16 17:02:33 UTC 2022 , Edited by admin on Fri Dec 16 17:02:33 UTC 2022
NON-SPECIFIC STEREOCHEMISTRY
ChEMBL
CHEMBL293492
Created by admin on Fri Dec 16 17:02:33 UTC 2022 , Edited by admin on Fri Dec 16 17:02:33 UTC 2022
PRIMARY
DAILYMED
SR60A3XG0F
Created by admin on Fri Dec 16 17:02:33 UTC 2022 , Edited by admin on Fri Dec 16 17:02:33 UTC 2022
PRIMARY
NCI_THESAURUS
C45678
Created by admin on Fri Dec 16 17:02:33 UTC 2022 , Edited by admin on Fri Dec 16 17:02:33 UTC 2022
CONCEPT Industrial Aid
CHEBI
16731
Created by admin on Fri Dec 16 17:02:33 UTC 2022 , Edited by admin on Fri Dec 16 17:02:33 UTC 2022
PRIMARY
NDF-RT
N0000175629
Created by admin on Fri Dec 16 17:02:33 UTC 2022 , Edited by admin on Fri Dec 16 17:02:33 UTC 2022
PRIMARY Increased Histamine Release [PE]
NSC
40346
Created by admin on Fri Dec 16 17:02:33 UTC 2022 , Edited by admin on Fri Dec 16 17:02:33 UTC 2022
PRIMARY
RXCUI
1368153
Created by admin on Fri Dec 16 17:02:33 UTC 2022 , Edited by admin on Fri Dec 16 17:02:33 UTC 2022
PRIMARY RxNorm
PUBCHEM
637511
Created by admin on Fri Dec 16 17:02:33 UTC 2022 , Edited by admin on Fri Dec 16 17:02:33 UTC 2022
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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