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
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+
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 |
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
Primary Target | Pharmacology | Condition | Potency |
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Target ID: P37231|||Q15179 Gene ID: 5468.0 Gene Symbol: PPARG Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/26227398 |
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Target ID: Q03181|||Q9BUD4 Gene ID: 5467.0 Gene Symbol: PPARD Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/26227398 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
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Noxious cold ion channel TRPA1 is activated by pungent compounds and bradykinin. | 2004 Mar 25 |
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Effects of vitamin E on the cinnamaldehyde-induced apoptotic mechanism in human PLC/PRF/5 cells. | 2004 Nov |
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TRPA1 and TRPM8 activation in humans: effects of cinnamaldehyde and menthol. | 2005 Jun 21 |
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Synthesis and biological evaluation of dimeric cinnamaldehydes as potent antitumor agents. | 2006 Apr 15 |
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Delayed occurrence of H-ras12V-induced hepatocellular carcinoma with long-term treatment with cinnamaldehydes. | 2006 Jan 20 |
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Antimutagenicity of cinnamaldehyde and vanillin in human cells: Global gene expression and possible role of DNA damage and repair. | 2007 Mar 1 |
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Effects of 3-phenyl-propenal on the expression of toll-like receptors and downstream signaling components on raw264.7 murine macrophages. | 2008 |
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Cinnamoyl-based Nrf2-activators targeting human skin cell photo-oxidative stress. | 2008 Aug 15 |
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Cross-desensitization of responses of rat trigeminal subnucleus caudalis neurons to cinnamaldehyde and menthol. | 2008 Jan 3 |
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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 |
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Role of p38 MAPK in the selective release of IL-8 induced by chemical allergen in naive THp-1 cells. | 2008 Mar |
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Effects of cinnamaldehyde on PGE2 release and TRPV4 expression in mouse cerebral microvascular endothelial cells induced by interleukin-1beta. | 2008 Mar |
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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 |
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TRPA1 agonists--allyl isothiocyanate and cinnamaldehyde--induce adrenaline secretion. | 2008 Oct |
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Role of TRPM8 and TRPA1 for cold allodynia in patients with cold injury. | 2008 Sep 30 |
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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 |
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The cinnamon-derived Michael acceptor cinnamic aldehyde impairs melanoma cell proliferation, invasiveness, and tumor growth. | 2009 Jan 15 |
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QGP-1 cells release 5-HT via TRPA1 activation; a model of human enterochromaffin cells. | 2009 Nov |
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A plasmacytoid dendritic cell (CD123+/CD11c-) based assay system to predict contact allergenicity of chemicals. | 2009 Oct 1 |
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Comparative DNA microarray analysis of human monocyte derived dendritic cells and MUTZ-3 cells exposed to the moderate skin sensitizer cinnamaldehyde. | 2009 Sep 15 |
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Influence of cinnamaldehyde on viral myocarditis in mice. | 2010 Aug |
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Involvement of TRPA1 in ET-1-induced pain-like behavior in mice. | 2010 Feb 17 |
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Identification of PDL-1 as a novel biomarker of sensitizer exposure in dendritic-like cells. | 2010 Sep |
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Human dental pulp fibroblasts express the "cold-sensing" transient receptor potential channels TRPA1 and TRPM8. | 2011 Apr |
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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 |
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The involvement of TRPA1 channel activation in the inflammatory response evoked by topical application of cinnamaldehyde to mice. | 2011 Jun 20 |
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Allyl isothiocyanates and cinnamaldehyde potentiate miniature excitatory postsynaptic inputs in the supraoptic nucleus in rats. | 2011 Mar 25 |
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Preferential activation of the vagal nodose nociceptive subtype by TRPA1 agonists in the guinea pig esophagus. | 2011 Oct |
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Spice oil cinnamaldehyde exhibits potent anticandidal activity against fluconazole resistant clinical isolates. | 2011 Oct |
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Effect of cigarette smoking on cough reflex induced by TRPV1 and TRPA1 stimulations. | 2012 Mar |
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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 |
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Development of a new in vitro skin sensitization assay (Epidermal Sensitization Assay; EpiSensA) using reconstructed human epidermis. | 2013 Dec |
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Allergic skin inflammation induced by chemical sensitizers is controlled by the transcription factor Nrf2. | 2013 Jul |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.clinicaltrials.gov/ct2/show/NCT00479973
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
Substance Class |
Chemical
Created
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Record UNII |
SR60A3XG0F
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Record Status |
Validated (UNII)
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NDF-RT |
N0000185508
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JECFA EVALUATION |
CINNAMALDEHYDE
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DSLD |
4144 (Number of products:6)
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EC SCIENTIFIC COMMITTEE ON CONSUMER SAFETY OPINION |
SCCS/1459/11
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16935
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N0000171131
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PRIMARY | Allergens [Chemical/Ingredient] | ||
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104-55-2
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SR60A3XG0F
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DTXSID6024834
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C012843
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N0000184306
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PRIMARY | Cell-mediated Immunity [PE] | ||
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SUB37595
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DB14184
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203-213-9
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m3568
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14371-10-9
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C76703
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1133897
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CINNAMALDEHYDE
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142921
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104-55-2
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CHEMBL293492
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SR60A3XG0F
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C45678
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CONCEPT | Industrial Aid | ||
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16731
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N0000175629
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PRIMARY | Increased Histamine Release [PE] | ||
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40346
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100000129171
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1368153
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PRIMARY | RxNorm | ||
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692
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637511
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Related Record | Type | Details | ||
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PARENT -> CONSTITUENT ALWAYS PRESENT | |||
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PARENT -> CONSTITUENT ALWAYS PRESENT |
ASSAY (GC)
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PARENT -> CONSTITUENT ALWAYS PRESENT | |||
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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.
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PARENT -> CONSTITUENT MAY BE PRESENT | |||
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PARENT -> CONSTITUENT ALWAYS PRESENT | |||
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TARGET -> AGONIST |
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ACTIVE MOIETY |