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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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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The melon fruit fly, Bactrocera cucurbitae: a review of its biology and management. | 2005 Dec 6 |
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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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Biotransformation of raspberry ketone and zingerone by cultured cells of Phytolacca americana. | 2007 Feb |
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Cancer preventive properties of ginger: a brief review. | 2007 May |
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[Effects of zingerone on fat storage in ovariectomized rats]. | 2008 Aug |
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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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Radiomodifying and anticlastogenic effect of Zingerone on Swiss albino mice exposed to whole body gamma radiation. | 2009 Jun-Jul |
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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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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 |
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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204-548-3
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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