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zingerone

Chemical Structure

General Material Information

Preferred name zingerone
Trivial Name Zingerone
Short Description vanillyl acetone
Formula C11 H14 O3
CAS Number 122-48-5
FEMA Number 3124
Flavis Number 7.005
ECHA Number 204-548-3
FDA UNII 4MMW850892
Nikkaji Number J5.356B
Beilstein Number 2051099
MDL MFCD00048232
COE Number 139
Bio Activity Summary External link
NMR Predictor External link
JECFA Food Flavoring 730 zingerone
FDA Patent No longer provide for the use of these seven synthetic flavoring substances
FDA Mainterm 122-48-5 ; ZINGERONE
Synonyms
  • butan-2-one, 4-(4-hydroxy-3-methoxyphenyl)-
  • 2-butanone, 4-(4-hydroxy-3-methoxyphenyl)-
  • 2-butanone, 4-(4-hydroxy-3-methoxyphenyl)-
  • ginger ketone
  • gingerone
  • 4-(4-hydroxy-3-methoxy-phenyl)-butan-2-one
  • 4-hydroxy-3-methoxybenzyl acetone
  • 4-hydroxy-3-methoxybenzylacetone
  • 2-(4-hydroxy-3-methoxyphenyl ethyl) methyl ketone
  • 4-(4-hydroxy-3-methoxyphenyl) butan-2-one
  • (4-hydroxy-3-methoxyphenyl) ethyl methyl ketone
  • 2-(4-hydroxy-3-methoxyphenyl) ethyl methyl ketone
  • 4-(4-hydroxy-3-methoxyphenyl)-2-butanone
  • 4-(4-hydroxy-3-methoxyphenyl)butan-2-one
  • (4-hydroxy-3-methoxyphenyl)ethyl methyl ketone
  • 2-(4-hydroxy-3-methoxyphenyl)ethyl methyl ketone
  • 4-hydroxy-3-methyoxyphenyl ethyl methyl ketone
  • 3-methoxy-4-hydroxy-benzylacetone
  • 3-methoxy-4-hydroxybenzyl acetone
  • 3-methoxy-4-hydroxybenzylacetone
  • 4-(3-methoxy-4-hydroxyphenyl)-2-butanone
  • 1-(3-methoxy-4-hydroxyphenyl)-3-butanone
  • [0]- paradol
  • vanillyl acetone
  • vanillylacetone
  • nat. zingerone
  • zingerone cong. solid
  • zingerone cryst. powder
  • zingerone natural
  • zingerone, natural
  • zingherone
  • zingiberone
  • 4-(4-hydroxy-3-methoxyphenyl)butan-2-one
  • 2-Butanone, 4-(4-hydroxy-3-methoxyphenyl)-
  • 4-(4-Hydroxy-3-methoxyphenyl)-2-butanone
  • 4-Hydroxy-3-methoxybenzylacetone
  • (4-Hydroxy-3-methoxyphenyl)ethyl methyl ketone
  • 3-Methoxy-4-hydroxybenzylacetone
  • [0]-Paradol
  • NSC 15335

US / EU / FDA / JECFA / FEMA / Scholar / Patents

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Literature & References

4-(4-hydroxy-3-methoxyphenyl)butan-2-one
NIST Chemistry WebBook:Search Inchi
Canada Domestic Sub. List:122-48-5
Pubchem (cid):31211
Pubchem (sid):134973883
Pherobase:View
Publications by PubMed
Synthesis and quorum sensing inhibitory activity of key phenolic compounds of ginger and their derivatives.
Ginger and its pungent constituents non-competitively inhibit serotonin currents on visceral afferent neurons.
Zingerone attenuates lipopolysaccharide-induced acute lung injury in mice.
Zingerone regulates intestinal transit, attenuates behavioral and oxidative perturbations in irritable bowel disorder in rats.
Delayed administration of zingerone mitigates the behavioral and histological alteration via repression of oxidative stress and intrinsic programmed cell death in focal transient ischemic rats.
Zingerone protects against stannous chloride-induced and hydrogen peroxide-induced oxidative DNA damage in vitro.
Chemopreventive effect of zingerone against colon carcinogenesis induced by 1,2-dimethylhydrazine in rats.
Anti-neuroinflammatory capacity of fresh ginger is attributed mainly to 10-gingerol.
Zingerone inhibit biofilm formation and improve antibiofilm efficacy of ciprofloxacin against Pseudomonas aeruginosa PAO1.
[Chemical constituents from leaves of Rhododendron rubiginosum var rubiginosum].
Influence of ginger and cinnamon intake on inflammation and muscle soreness endued by exercise in Iranian female athletes.
Zingerone enhances glutamatergic spontaneous excitatory transmission by activating TRPA1 but not TRPV1 channels in the adult rat substantia gelatinosa.
Small molecules interacting with α-synuclein: antiaggregating and cytoprotective properties.
Inhibition by capsaicin and its related vanilloids of compound action potentials in frog sciatic nerves.
In vitro antifungal activity of dehydrozingerone and its fungitoxic properties.
Synthesis of quinoline derivatives of tetrahydrocurcumin and zingerone and evaluation of their antioxidant and antibacterial attributes.
Fenugreek extract as an inducer of cellular death via autophagy in human T lymphoma Jurkat cells.
Ginger extract and zingerone ameliorated trinitrobenzene sulphonic acid-induced colitis in mice via modulation of nuclear factor-κB activity and interleukin-1β signalling pathway.
Radioprotective effects of Zingiber officinale Roscoe (ginger): past, present and future.
An overview on inventions related to ginger processing and products for food and pharmaceutical applications.
Dietary administration of zingerone to enhance growth, non-specific immune response, and resistance to Vibrio alginolyticus in Pacific white shrimp (Litopenaeus vannamei) juveniles.
Update on the chemopreventive effects of ginger and its phytochemicals.
Characterization of raspberry ketone/zingerone synthase, catalyzing the alpha, beta-hydrogenation of phenylbutenones in raspberry fruits.
Effects of zingerone [4-(4-hydroxy-3-methoxyphenyl)-2-butanone] and eugenol [2-methoxy-4-(2-propenyl)phenol] on the pathological progress in the 6-hydroxydopamine-induced Parkinson's disease mouse model.
Intraluminal administration of zingerol, a non-pungent analogue of zingerone, inhibits colonic motility in rats.
Protective effect of zingerone, a dietary compound against radiation induced genetic damage and apoptosis in human lymphocytes.
Inhibitory effects of zingerone, a pungent component of Zingiber officinale Roscoe, on colonic motility in rats.
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.
Effects of various fragrant ingredients on desmopressin-induced fluid retention in mice.
Modulation of age-related NF-kappaB activation by dietary zingerone via MAPK pathway.
Radiomodifying and anticlastogenic effect of Zingerone on Swiss albino mice exposed to whole body gamma radiation.
Peroxisome proliferator-activated receptor activation by a short-term feeding of zingerone in aged rats.
Ginger-derived phenolic substances with cancer preventive and therapeutic potential.
[Analysis of volatile and non-volatile compositions in ginger oleoresin by gas chromatography-mass spectrometry].
Alkaloid and sesquiterpenes from the root tuber of Curcuma longa.
Chemistry, antioxidant and antimicrobial investigations on essential oil and oleoresins of Zingiber officinale.
[Effects of zingerone on fat storage in ovariectomized rats].
Volatile composition in raspberry cultivars grown in the Pacific Northwest determined by stir bar sorptive extraction-gas chromatography-mass spectrometry.
Manganese peroxidase-catalyzed oxidative degradation of vanillylacetone.
Ginger and its bioactive component inhibit enterotoxigenic Escherichia coli heat-labile enterotoxin-induced diarrhea in mice.
Temporal interactions between oral irritants: piperine, zingerone, and capsaicin.
Biotransformation of raspberry ketone and zingerone by cultured cells of Phytolacca americana.
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.
Cancer preventive properties of ginger: a brief review.
Targeting antioxidative signal transduction and stress response system: control of pathogenic Aspergillus with phenolics that inhibit mitochondrial function.
Controlling food-contaminating fungi by targeting their antioxidative stress-response system with natural phenolic compounds.
Stimulatory actions of thymol, a natural product, on Ca(2+)-activated K(+) current in pituitary GH(3) cells.
Antioxidant and free radical scavenging activities of Misodendrum punctulatum, myzodendrone and structurally related phenols.
Zingerone as an antioxidant against peroxynitrite.
Zingerone [4-(4-hydroxy-3-methoxyphenyl)-2-butanone] prevents 6-hydroxydopamine-induced dopamine depression in mouse striatum and increases superoxide scavenging activity in serum.
Isolation of a natural antioxidant, dehydrozingerone from Zingiber officinale and synthesis of its analogues for recognition of effective antioxidant and antityrosinase agents.
Identification of phenolics for control of Aspergillus flavus using Saccharomyces cerevisiae in a model target-gene bioassay.
Inhibitory effect of ginger (Zingiber officinale) on rat ileal motility in vitro.
Effects of terpenoid phenol derivatives on calcium current in canine and human ventricular cardiomyocytes.
Individual differences in perception of bitterness from capsaicin, piperine and zingerone.
Use of a fluorescent imaging plate reader--based calcium assay to assess pharmacological differences between the human and rat vanilloid receptor.
Analysis of a ginger extract by high-performance liquid chromatography coupled to nuclear magnetic resonance spectroscopy using superheated deuterium oxide as the mobile phase.
Insect growth inhibition, antifeedant and antifungal activity of compounds isolated/derived from Zingiber officinale Roscoe (ginger) rhizomes.
Responses to repeated oral irritation by capsaicin, cinnamaldehyde and ethanol in PROP tasters and non-tasters.
Different responses to repeated applications of zingerone in behavioral studies, recordings from intact and cultured TG neurons, and from VR1 receptors.
Guaiacol and vanilloid compounds modulate the A-type potassium currents in molluscan neurons.
The generalizability of capsaicin sensitization and desensitization.
Induction of apoptosis in HL-60 cells by pungent vanilloids, [6]-gingerol and [6]-paradol.
The influence of removing extracellular Ca2+ in the desensitization responses to capsaicin, zingerone and olvanil in rat trigeminal ganglion neurons.
Rapid recovery from capsaicin desensitization during recurrent stimulation.
Desensitization to oral zingerone irritation: effects of stimulus parameters.
Similarities and differences in the currents activated by capsaicin, piperine, and zingerone in rat trigeminal ganglion cells.
Psychophysical responses to single and multiple presentations of the oral irritant zingerone: relationship to frequency of chili consumption.
Oxidation reactions catalyzed by manganese peroxidase isoenzymes from Ceriporiopsis subvermispora.
Oxidase of the white rot fungus Panus tigrinus 8/18.
Antioxidant actions of thymol, carvacrol, 6-gingerol, zingerone and hydroxytyrosol.
Scavenging of superoxide anions by spice principles.
Evidence that removal of capsaicin accelerates desensitization on the tongue.
Differential inhibition of potassium currents in rat ventricular myocytes by capsaicin.
Studies on spice principles as antioxidants in the inhibition of lipid peroxidation of rat liver microsomes.
Heterologous expression of active manganese peroxidase from Phanerochaete chrysosporium using the baculovirus expression system.
Characterization of vanilloid receptors in the dorsal horn of pig spinal cord.
Antimicrobial effectiveness of six paradols. 1: A structure-activity relationship study.
Some pungent principles of spices cause the adrenal medulla to secrete catecholamine in anesthetized rats.
Mutagenicity of gingerol and shogaol and antimutagenicity of zingerone in Salmonella/microsome assay.
A simple, sensitive method for detecting early peripheral nerve dysfunction in the rat following acrylamide treatment.
The active part of the [6]-gingerol molecule in mutagenesis.
Anaesthesia-like condition and/or potentiation of hexobarbital sleep produced by pungent agents in normal and capsaicin-desensitized rats.
Stimulation of prostaglandin biosynthesis by drugs: effects in vitro of some drugs affecting gut function.
The metabolism of zingerone, a pungent principle of ginger.
Sensory effects of capsaicin congeners. Part II: Importance of chemical structure and pungency in desensitizing activity of capsaicin-type compounds.
Homologs of dopa, alpha-methyldopa, and dopamine as potential cardiovascular drugs.
[On o-vanillylacetone and its hydrogenation products with a contribution to hydrogenating amination of ketones].

Other Information

(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
FDA Substances Added to Food (formerly EAFUS):View
CHEBI:View
CHEMBL:View
KEGG (GenomeNet):C17497
HMDB (The Human Metabolome Database):HMDB32590
FooDB:FDB010527
YMDB (Yeast Metabolome Database):YMDB01809
Typical G.C.
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View
Formulations/Preparations:
commercial product contains a minimum of 93% zingerone.

PhysChem Properties

Material listed in food chemical codex No
Molecular weight 194.23017883301
Melting Point 39 to 42°C @ 760 mm Hg
Boiling Point 141 to 0.5°C @ 0 mm Hg
Vapor Pressure 0.000143 mmHg @ 25 °C
Flash Point TCC Value 123.7 °C TCC
logP (o/w) 1.168 est
Solubility
ethyl alcohol, 1:1 in 50% alcohol Yes
water, 3571 mg/L @ 25 °C (est) Yes
Stability
no special storage precautions necessary Unspecified
non-discoloring Unspecified
stable in most media Unspecified

Organoleptic Properties

Odor Type: Spicy
sweet, spicy, phenolic, ginger, vanilla, woody, balsamic, creamy
Odor strength medium
Substantivity 337 hour(s) at 10.00 % in dipropylene glycol
Luebke, William tgsc, (1986) At 100.00 %. sweet spicy phenolic ginger vanilla woody
Mosciano, Gerard P&F 20, No. 1, 31, (1995) Spicy, phenolic and balsamic with a creamy vanilla-like nuance
Flavor Type: Spicy
ginger, spicy
Mosciano, Gerard P&F 20, No. 1, 31, (1995) At 80.00 ppm. Spicy with a biting, lingering heat

Occurrences

Safety Information

Safety information

Preferred SDS: View
Hazards identification
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
Pictogram
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
oral-rat LD50 2580 mg/kg
(Moreno, 1977ae)

oral-rat LD50 2580 mg/kg
Food and Chemical Toxicology. Vol. 20, Pg. 851, 1982.

Dermal Toxicity:
skin-rabbit LD50 > 5000 mg/kg
Food and Chemical Toxicology. Vol. 20, Pg. 851, 1982.

Inhalation Toxicity:
Not determined

Safety in use information

Category:
flavor and fragrance agents
RIFM Fragrance Material Safety Assessment: Search
IFRA Code of Practice Notification of the 49th Amendment to the IFRA Code of Practice
Recommendation for zingerone usage levels up to:
2.0000 % in the fragrance concentrate.
Maximised Survey-derived Daily Intakes (MSDI-EU): 34.00 (μg/capita/day)
Maximised Survey-derived Daily Intakes (MSDI-USA): 83.00 (μg/capita/day)
Use levels for FEMA GRAS flavoring substances on which the FEMA Expert Panel based its judgments that the substances are generally recognized as safe (GRAS).
The Expert Panel also publishes separate extensive reviews of scientific information on all FEMA GRAS flavoring substances and can be found at FEMA Flavor Ingredient Library
publication number: 3
Click here to view publication 3
average usual ppmaverage maximum ppm
baked goods: -11.00000
beverages(nonalcoholic): -6.90000
beverages(alcoholic): --
breakfast cereal: --
cheese: --
chewing gum: -15.00000
condiments / relishes: --
confectionery froastings: --
egg products: --
fats / oils: --
fish products: --
frozen dairy: -7.80000
fruit ices: -7.80000
gelatins / puddings: --
granulated sugar: --
gravies: --
hard candy: -11.00000
imitation dairy: --
instant coffee / tea: --
jams / jellies: --
meat products: --
milk products: --
nut products: --
other grains: --
poultry: --
processed fruits: --
processed vegetables: --
reconstituted vegetables: --
seasonings / flavors: --
snack foods: --
soft candy: --
soups: --
sugar substitutes: --
sweet sauces: --

Safety references

European Food Safety Athority(EFSA):Flavor usage levels; Subacute, Subchronic, Chronic and Carcinogenicity Studies; Developmental / Reproductive Toxicity Studies; Genotoxicity Studies...

European Food Safety Authority (EFSA) reference(s):

Opinion of the Scientific Panel on food additives, flavourings, processing aids and materials in contact with food (AFC) related to Flavouring Group Evaluation 22 (FGE.22): Ring-substituted phenolic substances from chemical groups 21 and 25 (Commission Regulation (EC) No 1565/2000 of 18 July 2000)
View page or View pdf

Flavouring Group Evaluation 58 (FGE.58) Consideration of phenol derivatives evaluated by JECFA (55th meeting) structurally related to ring substituted phenolic substances evaluated by EFSA in FGE.22 (2006) (Commission Regulation (EC) No 1565/2000 of 18 July 2000) - Opinion of the Scientific Panel on Food Additives, Flavourings, Processing Aids and Materials in contact with Food (AFC)
View page or View pdf

Flavouring Group Evaluation 60 (FGE.60): Consideration of eugenol and related hydroxyallylbenzene derivatives evaluated by JECFA (65th meeting) structurally related to ring- substituted phenolic substances evaluated by EFSA in FGE.22 (2006)
View page or View pdf

Scientific Opinion on Flavouring Group Evaluation 22, Revision 1 (FGE.22Rev1): Ring-substituted phenolic substances from chemical groups 21 and 25
View page or View pdf

Safety and efficacy of aromatic ketones, secondary alcohols and related esters belonging to chemical group 21 when used as flavourings for all animal species
View page or View pdf

EPI System: View
Chemical Carcinogenesis Research Information System:Search
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA Substance Registry Services (TSCA):122-48-5
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :31211
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:2
4-(4-hydroxy-3-methoxyphenyl)butan-2-one
Chemidplus:0000122485
RTECS:EL8900000 for cas# 122-48-5