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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

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.

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
Stimulatory actions of thymol, a natural product, on Ca(2+)-activated K(+) current in pituitary GH(3) cells.
2005 Dec
The melon fruit fly, Bactrocera cucurbitae: a review of its biology and management.
2005 Dec 6
Targeting antioxidative signal transduction and stress response system: control of pathogenic Aspergillus with phenolics that inhibit mitochondrial function.
2006 Jul
Effects of a combination of thyme and oregano essential oils on TNBS-induced colitis in mice.
2007
Temporal interactions between oral irritants: piperine, zingerone, and capsaicin.
2007 Jun
Ginger and its bioactive component inhibit enterotoxigenic Escherichia coli heat-labile enterotoxin-induced diarrhea in mice.
2007 Oct 17
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
[Analysis of volatile and non-volatile compositions in ginger oleoresin by gas chromatography-mass spectrometry].
2008 Nov
Effects of various fragrant ingredients on desmopressin-induced fluid retention in mice.
2010 Jul
Indian spices for healthy heart - an overview.
2010 Nov
Antioxidant enrichment and antimicrobial protection of fresh-cut fruits using their own byproducts: looking for integral exploitation.
2010 Oct
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.
Substance Class Chemical
Created
by admin
on Fri Dec 15 17:35:12 GMT 2023
Edited
by admin
on Fri Dec 15 17:35:12 GMT 2023
Record UNII
4MMW850892
Record Status Validated (UNII)
Record Version
  • Download
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