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
Molecular Formula | C11H14O3 |
Molecular Weight | 194.2271 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
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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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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Effects of a combination of thyme and oregano essential oils on TNBS-induced colitis in mice. | 2007 |
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Temporal interactions between oral irritants: piperine, zingerone, and capsaicin. | 2007 Jun |
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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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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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[Analysis of volatile and non-volatile compositions in ginger oleoresin by gas chromatography-mass spectrometry]. | 2008 Nov |
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Effects of various fragrant ingredients on desmopressin-induced fluid retention in mice. | 2010 Jul |
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Indian spices for healthy heart - an overview. | 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 |
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.
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 17:35:12 GMT 2023
by
admin
on
Fri Dec 15 17:35:12 GMT 2023
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Record UNII |
4MMW850892
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Record Status |
Validated (UNII)
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Record Version |
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Classification Tree | Code System | Code | ||
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JECFA EVALUATION |
ZINGERONE
Created by
admin on Fri Dec 15 17:35:12 GMT 2023 , Edited by admin on Fri Dec 15 17:35:12 GMT 2023
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DSLD |
3145 (Number of products:7)
Created by
admin on Fri Dec 15 17:35:12 GMT 2023 , Edited by admin on Fri Dec 15 17:35:12 GMT 2023
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CFR |
21 CFR 172.515
Created by
admin on Fri Dec 15 17:35:12 GMT 2023 , Edited by admin on Fri Dec 15 17:35:12 GMT 2023
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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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122-48-5
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