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 |
|---|---|---|---|
Target ID: P37231|||Q15179 Gene ID: 5468.0 Gene Symbol: PPARG Target Organism: Homo sapiens (Human) |
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Target ID: Q03181|||Q9BUD4 Gene ID: 5467.0 Gene Symbol: PPARD Target Organism: Homo sapiens (Human) |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Unknown Approved UseUnknown |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Regulatory effect of cinnamaldehyde on monocyte/macrophage-mediated inflammatory responses. | 2010 |
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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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| Tacrolimus modulates dendritic cell activation in the sensitization phase of allergic contact dermatitis. | 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 impairs high glucose-induced hypertrophy in renal interstitial fibroblasts. | 2010 Apr 15 |
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| Influence of cinnamaldehyde on viral myocarditis in mice. | 2010 Aug |
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| Acetaminophen, via its reactive metabolite N-acetyl-p-benzo-quinoneimine and transient receptor potential ankyrin-1 stimulation, causes neurogenic inflammation in the airways and other tissues in rodents. | 2010 Dec |
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| Differential effects of substance P or hemokinin-1 on transient receptor potential channels, TRPV1, TRPA1 and TRPM8, in the rat. | 2010 Feb |
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| Involvement of TRPA1 in ET-1-induced pain-like behavior in mice. | 2010 Feb 17 |
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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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| High-throughput gene expression analysis of intestinal intraepithelial lymphocytes after oral feeding of carvacrol, cinnamaldehyde, or Capsicum oleoresin. | 2010 Jan |
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| The glutaredoxin/glutathione system modulates NF-kappaB activity by glutathionylation of p65 in cinnamaldehyde-treated endothelial cells. | 2010 Jul |
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| Gene markers in dendritic cells unravel pieces of the skin sensitization puzzle. | 2010 Jul 1 |
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| TRPA1-expressing primary afferents synapse with a morphologically identified subclass of substantia gelatinosa neurons in the adult rat spinal cord. | 2010 Jun |
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| Insulinotropic effect of cinnamaldehyde on transcriptional regulation of pyruvate kinase, phosphoenolpyruvate carboxykinase, and GLUT4 translocation in experimental diabetic rats. | 2010 Jun 7 |
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| Prediction of the contact sensitizing potential of chemicals using analysis of gene expression changes in human THP-1 monocytes. | 2010 Nov 10 |
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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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| Evidence for the pathophysiological relevance of TRPA1 receptors in the cardiovascular system in vivo. | 2010 Sep 1 |
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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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| The intra- and inter-laboratory reproducibility and predictivity of the KeratinoSens assay to predict skin sensitizers in vitro: results of a ring-study in five laboratories. | 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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| Transient receptor potential ankyrin 1 is expressed by inhibitory motoneurons of the mouse intestine. | 2011 Aug |
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| Sensitivity of bronchopulmonary receptors to cold and heat mediated by transient receptor potential cation channel subtypes in an ex vivo rat lung preparation. | 2011 Aug 15 |
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| Effects of cinnamaldehyde on the glucose transport activity of GLUT1. | 2011 Feb |
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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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| A novel human volunteer pain model using contact heat evoked potentials (CHEP) following topical skin application of transient receptor potential agonists capsaicin, menthol and cinnamaldehyde. | 2011 Jul |
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| [Mechanism of cinnamic aldehyde-inducing apoptosis of chronic myeloid leukemic cells in vitro]. | 2011 Jun |
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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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| Isopentenyl pyrophosphate is a novel antinociceptive substance that inhibits TRPV3 and TRPA1 ion channels. | 2011 May |
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| Antifungal activity of essential oils and their synergy with fluconazole against drug-resistant strains of Aspergillus fumigatus and Trichophyton rubrum. | 2011 May |
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| Cinnamaldehyde enhances Nrf2 nuclear translocation to upregulate phase II detoxifying enzyme expression in HepG2 cells. | 2011 May 11 |
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| Antifungal activity of redox-active benzaldehydes that target cellular antioxidation. | 2011 May 31 |
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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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| 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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| Contact sensitizers modulate the arachidonic acid metabolism of PMA-differentiated U-937 monocytic cells activated by LPS. | 2011 Oct 1 |
|
| Methylglyoxal activates the human transient receptor potential ankyrin 1 channel. | 2012 |
|
| Reduction of Salmonella enterica serovar enteritidis colonization in 20-day-old broiler chickens by the plant-derived compounds trans-cinnamaldehyde and eugenol. | 2012 Apr |
|
| 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 |
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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 |
|
| 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 |
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| 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
Sample Use Guides
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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Validated (UNII)
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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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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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692
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637511
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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 |
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ACTIVE MOIETY |
