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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Human skin absorption and metabolism of the contact allergens, cinnamic aldehyde, and cinnamic alcohol. | 2000 Nov 1 |
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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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Peptidyl aldehydes as reversible covalent inhibitors of protein tyrosine phosphatases. | 2002 Aug 27 |
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Deodorants: an experimental provocation study with cinnamic aldehyde. | 2003 Feb |
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Protein binding and metabolism influence the relative skin sensitization potential of cinnamic compounds. | 2004 Mar |
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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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Cinnamaldehyde reduction of platelet aggregation and thrombosis in rodents. | 2007 |
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Sensitization of TRPA1 by PAR2 contributes to the sensation of inflammatory pain. | 2007 Jul |
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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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Effects of TRPA1 agonists mustard oil and cinnamaldehyde on lumbar spinal wide-dynamic range neuronal responses to innocuous and noxious cutaneous stimuli in rats. | 2008 Feb |
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Cinnamaldehyde inhibits pro-inflammatory cytokines secretion from monocytes/macrophages through suppression of intracellular signaling. | 2008 Jan |
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Modulation of oral heat and cold pain by irritant chemicals. | 2008 Jan |
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Cinnamaldehyde suppresses toll-like receptor 4 activation mediated through the inhibition of receptor oligomerization. | 2008 Jan 15 |
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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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Role of TRPM8 and TRPA1 for cold allodynia in patients with cold injury. | 2008 Sep 30 |
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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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Cinnamaldehyde impairs high glucose-induced hypertrophy in renal interstitial fibroblasts. | 2010 Apr 15 |
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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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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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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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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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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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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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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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Effect of cigarette smoking on cough reflex induced by TRPV1 and TRPA1 stimulations. | 2012 Mar |
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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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Small molecules inhibit growth, viability and ergosterol biosynthesis in Candida albicans. | 2013 Dec |
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
by
admin
on
Edited
Wed Jul 05 22:55:04 UTC 2023
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on
Wed Jul 05 22:55:04 UTC 2023
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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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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 |
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ACTIVE MOIETY |