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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
Structure of ZINGERONE

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

HIDE SMILES / InChI
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.

Originator

Sources: DOI: 10.1039/CT9171100769

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Insect growth inhibition, antifeedant and antifungal activity of compounds isolated/derived from Zingiber officinale Roscoe (ginger) rhizomes.
2001 Mar
Use of a fluorescent imaging plate reader--based calcium assay to assess pharmacological differences between the human and rat vanilloid receptor.
2002 Oct
Effect of thymol on kinetic properties of Ca and K currents in rat skeletal muscle.
2003 Jul 15
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
Inhibitory effect of ginger (Zingiber officinale) on rat ileal motility in vitro.
2004 Apr 23
Identification of phenolics for control of Aspergillus flavus using Saccharomyces cerevisiae in a model target-gene bioassay.
2004 Dec 29
Individual differences in perception of bitterness from capsaicin, piperine and zingerone.
2004 Jan
Effects of terpenoid phenol derivatives on calcium current in canine and human ventricular cardiomyocytes.
2004 Mar 8
Stimulatory actions of thymol, a natural product, on Ca(2+)-activated K(+) current in pituitary GH(3) cells.
2005 Dec
Antioxidant and free radical scavenging activities of Misodendrum punctulatum, myzodendrone and structurally related phenols.
2005 Dec
The melon fruit fly, Bactrocera cucurbitae: a review of its biology and management.
2005 Dec 6
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
Isolation of a natural antioxidant, dehydrozingerone from Zingiber officinale and synthesis of its analogues for recognition of effective antioxidant and antityrosinase agents.
2005 May
Identification of natural dyes used in works of art by pyrolysis-gas chromatography/mass spectrometry combined with in situ trimethylsilylation.
2005 May
Zingerone as an antioxidant against peroxynitrite.
2005 Sep 21
Targeting antioxidative signal transduction and stress response system: control of pathogenic Aspergillus with phenolics that inhibit mitochondrial function.
2006 Jul
Controlling food-contaminating fungi by targeting their antioxidative stress-response system with natural phenolic compounds.
2006 May
Effects of a combination of thyme and oregano essential oils on TNBS-induced colitis in mice.
2007
Biotransformation of raspberry ketone and zingerone by cultured cells of Phytolacca americana.
2007 Feb
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
Temporal interactions between oral irritants: piperine, zingerone, and capsaicin.
2007 Jun
Cancer preventive properties of ginger: a brief review.
2007 May
Ginger and its bioactive component inhibit enterotoxigenic Escherichia coli heat-labile enterotoxin-induced diarrhea in mice.
2007 Oct 17
[Effects of zingerone on fat storage in ovariectomized rats].
2008 Aug
Alkaloid and sesquiterpenes from the root tuber of Curcuma longa.
2008 Jul
Manganese peroxidase-catalyzed oxidative degradation of vanillylacetone.
2008 Jun
Volatile composition in raspberry cultivars grown in the Pacific Northwest determined by stir bar sorptive extraction-gas chromatography-mass spectrometry.
2008 Jun 11
Herbal compounds and toxins modulating TRP channels.
2008 Mar
ThermoTRP channels in nociceptors: taking a lead from capsaicin receptor TRPV1.
2008 Mar
Herb-drug interaction: a case study of effect of ginger on the pharmacokinetic of metronidazole in rabbit.
2008 Mar-Apr
[Analysis of volatile and non-volatile compositions in ginger oleoresin by gas chromatography-mass spectrometry].
2008 Nov
Chemistry, antioxidant and antimicrobial investigations on essential oil and oleoresins of Zingiber officinale.
2008 Oct
Ginger-derived phenolic substances with cancer preventive and therapeutic potential.
2009
Peroxisome proliferator-activated receptor activation by a short-term feeding of zingerone in aged rats.
2009 Apr
Phytoremediation of benzophenone and bisphenol a by glycosylation with immobilized plant cells.
2009 Apr 6
Radiomodifying and anticlastogenic effect of Zingerone on Swiss albino mice exposed to whole body gamma radiation.
2009 Jun-Jul
Bioremediation of Bisphenol A and Benzophenone by Glycosylation with Immobilized Marine Microalga Pavlova sp.
2009 Sep 23
Effect of essential oils, such as raspberry ketone and its derivatives, on antiandrogenic activity based on in vitro reporter gene assay.
2010 Apr 1
Effects of various fragrant ingredients on desmopressin-induced fluid retention in mice.
2010 Jul
Modulation of age-related NF-kappaB activation by dietary zingerone via MAPK pathway.
2010 Jun
Subinhibitory concentrations of thymol reduce enterotoxins A and B and alpha-hemolysin production in Staphylococcus aureus isolates.
2010 Mar 17
Psychophysical evaluation of a sanshool derivative (alkylamide) and the elucidation of mechanisms subserving tingle.
2010 Mar 3
Indian spices for healthy heart - an overview.
2010 Nov
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
Antioxidant enrichment and antimicrobial protection of fresh-cut fruits using their own byproducts: looking for integral exploitation.
2010 Oct
Moving towards supraspinal TRPV1 receptors for chronic pain relief.
2010 Oct 11
The mouse eugenol odorant receptor: structural and functional plasticity of a broadly tuned odorant binding pocket.
2011 Feb 8
Patents

Sample Use Guides

Rat: 10, 20 or 40 mg/kg body weight
Route of Administration: Oral
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.
Name Type Language
ZINGERONE
FCC   FHFI   HSDB   INCI   MI  
INCI  
Official Name English
NSC-15335
Code English
FEMA NO. 3124
Code English
4-(4-HYDROXY-3-METHOXYPHENYL)-2-BUTANONE
Systematic Name English
ZINGIBERONE
Common Name English
Vanillylaceton [WHO-DD]
Common Name English
VANILLYLACETON
WHO-DD  
Systematic Name English
ZINGHERONE
Common Name English
VANILLYLACETONE
Systematic Name English
ZINGERONE [HSDB]
Common Name English
ZINGERONE [INCI]
Common Name English
(4-HYDROXY-3-METHOXYPHENYL)ETHYL METHYL KETONE
Systematic Name English
ZINGERONE [MI]
Common Name English
ZINGERONE [FCC]
Common Name English
2-BUTANONE, 4-(4-HYDROXY-3-METHOXYPHENYL)-
Systematic Name English
ZINGERONE [FHFI]
Common Name English
Classification Tree Code System Code
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
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
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
Code System Code Type Description
FDA UNII
4MMW850892
Created by admin on Fri Dec 15 17:35:12 GMT 2023 , Edited by admin on Fri Dec 15 17:35:12 GMT 2023
PRIMARY
DRUG BANK
DB15589
Created by admin on Fri Dec 15 17:35:12 GMT 2023 , Edited by admin on Fri Dec 15 17:35:12 GMT 2023
PRIMARY
SMS_ID
100000167016
Created by admin on Fri Dec 15 17:35:12 GMT 2023 , Edited by admin on Fri Dec 15 17:35:12 GMT 2023
PRIMARY
WIKIPEDIA
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
PRIMARY
MERCK INDEX
m11636
Created by admin on Fri Dec 15 17:35:12 GMT 2023 , Edited by admin on Fri Dec 15 17:35:12 GMT 2023
PRIMARY Merck Index
EVMPD
SUB15687MIG
Created by admin on Fri Dec 15 17:35:12 GMT 2023 , Edited by admin on Fri Dec 15 17:35:12 GMT 2023
PRIMARY
NSC
15335
Created by admin on Fri Dec 15 17:35:12 GMT 2023 , Edited by admin on Fri Dec 15 17:35:12 GMT 2023
PRIMARY
ECHA (EC/EINECS)
204-548-3
Created by admin on Fri Dec 15 17:35:12 GMT 2023 , Edited by admin on Fri Dec 15 17:35:12 GMT 2023
PRIMARY
JECFA MONOGRAPH
602
Created by admin on Fri Dec 15 17:35:12 GMT 2023 , Edited by admin on Fri Dec 15 17:35:12 GMT 2023
PRIMARY
DAILYMED
4MMW850892
Created by admin on Fri Dec 15 17:35:12 GMT 2023 , Edited by admin on Fri Dec 15 17:35:12 GMT 2023
PRIMARY
RXCUI
2199325
Created by admin on Fri Dec 15 17:35:12 GMT 2023 , Edited by admin on Fri Dec 15 17:35:12 GMT 2023
PRIMARY
CAS
122-48-5
Created by admin on Fri Dec 15 17:35:12 GMT 2023 , Edited by admin on Fri Dec 15 17:35:12 GMT 2023
PRIMARY
MESH
C013738
Created by admin on Fri Dec 15 17:35:12 GMT 2023 , Edited by admin on Fri Dec 15 17:35:12 GMT 2023
PRIMARY
PUBCHEM
31211
Created by admin on Fri Dec 15 17:35:12 GMT 2023 , Edited by admin on Fri Dec 15 17:35:12 GMT 2023
PRIMARY
EPA CompTox
DTXSID8047420
Created by admin on Fri Dec 15 17:35:12 GMT 2023 , Edited by admin on Fri Dec 15 17:35:12 GMT 2023
PRIMARY
EVMPD
SUB181345
Created by admin on Fri Dec 15 17:35:12 GMT 2023 , Edited by admin on Fri Dec 15 17:35:12 GMT 2023
PRIMARY
HSDB
1064
Created by admin on Fri Dec 15 17:35:12 GMT 2023 , Edited by admin on Fri Dec 15 17:35:12 GMT 2023
PRIMARY
CHEBI
68657
Created by admin on Fri Dec 15 17:35:12 GMT 2023 , Edited by admin on Fri Dec 15 17:35:12 GMT 2023
PRIMARY