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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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 |
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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 |
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More than cool: promiscuous relationships of menthol and other sensory compounds. | 2006 Aug |
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Cinnamaldehyde reduces IL-1beta-induced cyclooxygenase-2 activity in rat cerebral microvascular endothelial cells. | 2006 May 10 |
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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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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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The cinnamon-derived Michael acceptor cinnamic aldehyde impairs melanoma cell proliferation, invasiveness, and tumor growth. | 2009 Jan 15 |
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High-resolution transcriptional profiling of chemical-stimulated dendritic cells identifies immunogenic contact allergens, but not prohaptens. | 2010 |
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Behavioral evidence of thermal hyperalgesia and mechanical allodynia induced by intradermal cinnamaldehyde in rats. | 2010 Apr 12 |
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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 |
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Gene markers in dendritic cells unravel pieces of the skin sensitization puzzle. | 2010 Jul 1 |
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Evidence for the pathophysiological relevance of TRPA1 receptors in the cardiovascular system in vivo. | 2010 Sep 1 |
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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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Transient receptor potential ankyrin 1 is expressed by inhibitory motoneurons of the mouse intestine. | 2011 Aug |
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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 |
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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 |
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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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Comparative study of the possible protective effects of cinnamic acid and cinnamaldehyde on cisplatin-induced nephrotoxicity in rats. | 2013 Dec |
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Allergic skin inflammation induced by chemical sensitizers is controlled by the transcription factor Nrf2. | 2013 Jul |
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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
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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admin
on
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Fri Dec 16 17:02:33 UTC 2022
by
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on
Fri Dec 16 17:02:33 UTC 2022
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Record UNII |
SR60A3XG0F
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Record Status |
Validated (UNII)
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Classification Tree | Code System | Code | ||
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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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Code System | Code | Type | Description | ||
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16935
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PRIMARY | |||
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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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NON-SPECIFIC STEREOCHEMISTRY | |||
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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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1368153
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PRIMARY | RxNorm | ||
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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 | |||
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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 |
Related Record | Type | Details | ||
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ACTIVE MOIETY |