Details
Stereochemistry | ACHIRAL |
Molecular Formula | C11H14O3 |
Molecular Weight | 194.2271 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
COC1=CC(CCC(C)=O)=CC=C1O
InChI
InChIKey=OJYLAHXKWMRDGS-UHFFFAOYSA-N
InChI=1S/C11H14O3/c1-8(12)3-4-9-5-6-10(13)11(7-9)14-2/h5-7,13H,3-4H2,1-2H3
Zingerone is one of the active phenolic components isolated from Zingiber officinale. Zingerone is primarily present in dry ginger, but cooking or drying also converts gingerol into zingerone by a retroaldol reaction. Chemically synthesized zingerone is vanillyl acetone, which is a member of the phenolic alkanone group, and its varied pharmacological properties include antioxidant, anti-inflammatory, and anticancer activities. Thus, zingeroneshowed strong anti-angiogenic activity via the inhibition of MMP-2 and MMP-9 during tumor progression. Zingerone was likely to be broad-spectrum anti-inflammatory agents in most organs that suppressed the activation of NF-κB, the production of IL-1β, and the infiltration of inflammatory cells in mice. Zingerone effectively inhibits 1,2-dimethylhydrazine-induced colon carcinogenesis in male Wistar rats. Zingerone possess radioprotective effects in laboratory animals and in cultured cells in vitro. Zingerone produced marked improvement in stress induced irritable bowel disorder, which could be attributed to the powerful antioxidant nature, direct effect on the intestinal smooth muscle and adaptogenic nature. Analysis of the qualities that constituted zingerone irritation found that the sensations produced are predominantly burning and warmth, making it qualitatively similar to capsaicin.
CNS Activity
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: GO:0038061 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26073629 |
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Target ID: GO:0007254 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27323807 |
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Target ID: WP408 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24262066 |
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Target ID: CHEMBL2094116 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24757377 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
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Insect growth inhibition, antifeedant and antifungal activity of compounds isolated/derived from Zingiber officinale Roscoe (ginger) rhizomes. | 2001 Mar |
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Use of a fluorescent imaging plate reader--based calcium assay to assess pharmacological differences between the human and rat vanilloid receptor. | 2002 Oct |
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Effect of thymol on kinetic properties of Ca and K currents in rat skeletal muscle. | 2003 Jul 15 |
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Analysis of a ginger extract by high-performance liquid chromatography coupled to nuclear magnetic resonance spectroscopy using superheated deuterium oxide as the mobile phase. | 2003 Mar 28 |
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Inhibitory effect of ginger (Zingiber officinale) on rat ileal motility in vitro. | 2004 Apr 23 |
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Identification of phenolics for control of Aspergillus flavus using Saccharomyces cerevisiae in a model target-gene bioassay. | 2004 Dec 29 |
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Individual differences in perception of bitterness from capsaicin, piperine and zingerone. | 2004 Jan |
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Effects of terpenoid phenol derivatives on calcium current in canine and human ventricular cardiomyocytes. | 2004 Mar 8 |
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Stimulatory actions of thymol, a natural product, on Ca(2+)-activated K(+) current in pituitary GH(3) cells. | 2005 Dec |
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Antioxidant and free radical scavenging activities of Misodendrum punctulatum, myzodendrone and structurally related phenols. | 2005 Dec |
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The melon fruit fly, Bactrocera cucurbitae: a review of its biology and management. | 2005 Dec 6 |
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Zingerone [4-(4-hydroxy-3-methoxyphenyl)-2-butanone] prevents 6-hydroxydopamine-induced dopamine depression in mouse striatum and increases superoxide scavenging activity in serum. | 2005 Mar |
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Isolation of a natural antioxidant, dehydrozingerone from Zingiber officinale and synthesis of its analogues for recognition of effective antioxidant and antityrosinase agents. | 2005 May |
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Identification of natural dyes used in works of art by pyrolysis-gas chromatography/mass spectrometry combined with in situ trimethylsilylation. | 2005 May |
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Zingerone as an antioxidant against peroxynitrite. | 2005 Sep 21 |
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Targeting antioxidative signal transduction and stress response system: control of pathogenic Aspergillus with phenolics that inhibit mitochondrial function. | 2006 Jul |
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Controlling food-contaminating fungi by targeting their antioxidative stress-response system with natural phenolic compounds. | 2006 May |
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Effects of a combination of thyme and oregano essential oils on TNBS-induced colitis in mice. | 2007 |
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Biotransformation of raspberry ketone and zingerone by cultured cells of Phytolacca americana. | 2007 Feb |
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Active spice-derived components can inhibit inflammatory responses of adipose tissue in obesity by suppressing inflammatory actions of macrophages and release of monocyte chemoattractant protein-1 from adipocytes. | 2007 Feb 13 |
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Temporal interactions between oral irritants: piperine, zingerone, and capsaicin. | 2007 Jun |
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Cancer preventive properties of ginger: a brief review. | 2007 May |
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Ginger and its bioactive component inhibit enterotoxigenic Escherichia coli heat-labile enterotoxin-induced diarrhea in mice. | 2007 Oct 17 |
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[Effects of zingerone on fat storage in ovariectomized rats]. | 2008 Aug |
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Alkaloid and sesquiterpenes from the root tuber of Curcuma longa. | 2008 Jul |
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Manganese peroxidase-catalyzed oxidative degradation of vanillylacetone. | 2008 Jun |
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Volatile composition in raspberry cultivars grown in the Pacific Northwest determined by stir bar sorptive extraction-gas chromatography-mass spectrometry. | 2008 Jun 11 |
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Herbal compounds and toxins modulating TRP channels. | 2008 Mar |
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ThermoTRP channels in nociceptors: taking a lead from capsaicin receptor TRPV1. | 2008 Mar |
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Herb-drug interaction: a case study of effect of ginger on the pharmacokinetic of metronidazole in rabbit. | 2008 Mar-Apr |
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[Analysis of volatile and non-volatile compositions in ginger oleoresin by gas chromatography-mass spectrometry]. | 2008 Nov |
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Chemistry, antioxidant and antimicrobial investigations on essential oil and oleoresins of Zingiber officinale. | 2008 Oct |
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Ginger-derived phenolic substances with cancer preventive and therapeutic potential. | 2009 |
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Peroxisome proliferator-activated receptor activation by a short-term feeding of zingerone in aged rats. | 2009 Apr |
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Phytoremediation of benzophenone and bisphenol a by glycosylation with immobilized plant cells. | 2009 Apr 6 |
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Radiomodifying and anticlastogenic effect of Zingerone on Swiss albino mice exposed to whole body gamma radiation. | 2009 Jun-Jul |
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Bioremediation of Bisphenol A and Benzophenone by Glycosylation with Immobilized Marine Microalga Pavlova sp. | 2009 Sep 23 |
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Effect of essential oils, such as raspberry ketone and its derivatives, on antiandrogenic activity based on in vitro reporter gene assay. | 2010 Apr 1 |
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Effects of various fragrant ingredients on desmopressin-induced fluid retention in mice. | 2010 Jul |
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Modulation of age-related NF-kappaB activation by dietary zingerone via MAPK pathway. | 2010 Jun |
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Subinhibitory concentrations of thymol reduce enterotoxins A and B and alpha-hemolysin production in Staphylococcus aureus isolates. | 2010 Mar 17 |
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Psychophysical evaluation of a sanshool derivative (alkylamide) and the elucidation of mechanisms subserving tingle. | 2010 Mar 3 |
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Indian spices for healthy heart - an overview. | 2010 Nov |
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Antagonistic effects of Zingerone, a phenolic alkanone against radiation-induced cytotoxicity, genotoxicity, apoptosis and oxidative stress in Chinese hamster lung fibroblast cells growing in vitro. | 2010 Nov |
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Antioxidant enrichment and antimicrobial protection of fresh-cut fruits using their own byproducts: looking for integral exploitation. | 2010 Oct |
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Moving towards supraspinal TRPV1 receptors for chronic pain relief. | 2010 Oct 11 |
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The mouse eugenol odorant receptor: structural and functional plasticity of a broadly tuned odorant binding pocket. | 2011 Feb 8 |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/23903760
Rat: 10, 20 or 40 mg/kg body weight
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/27323807
To investigate whether zingerone regulates the activities of MMPs, gelatin-based zymography using conditioned media from Renca cells was performed. The gelatinase activities of MMP-2 and MMP-9 were increased under hypoxic conditions, but zingerone (1 and 2 mM) treatment decreased these activities. 1 or 2 mM of zingerone significantly decreased expression of MMP-2 in Renca cells.
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Classification Tree | Code System | Code | ||
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JECFA EVALUATION |
ZINGERONE
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DSLD |
3145 (Number of products:7)
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CFR |
21 CFR 172.515
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4MMW850892
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DB15589
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100000167016
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ZINGERONE
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m11636
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SUB15687MIG
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4MMW850892
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2199325
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122-48-5
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C013738
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31211
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DTXSID8047420
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SUB181345
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SUBSTANCE RECORD