Identification

Namezingerone
IUPAC4-(4-hydroxy-3-methoxyphenyl)butan-2-one
CAS Number122-48-5
EINECS204-548-3
FDA UNII4MMW850892
Molecular FormulaC11 H14 O3
Molecular Weight194.23018000
MDL NumberMFCD00048232
Nikkaji NumberJ5.356B
Beilstein2051099
CoE Number139
XlogP30.80 (est)

Regulatory

JECFA Food Flavoring730 zingerone
DG SANTE Food Flavourings07.005 vanillyl acetone
FEMA Number3124
FDANo longer provide for the use of these seven synthetic flavoring substances
FDA Mainterm (SATF)122-48-5 ; ZINGERONE
FDA RegulationFDA PART 172 -- FOOD ADDITIVES PERMITTED FOR DIRECT ADDITION TO FOOD FOR HUMAN CONSUMPTION

Physical Properties

Appearance yellow to yellow brown crystals (est)
Assay 96.00 to 100.00
Food Chemicals Codex Listed No
Melting Point 39.00 to 42.00 °C. @ 760.00 mm Hg
Boiling Point 141.00 to 0.50 °C. @ 0.00 mm Hg, 290.00 °C. @ 760.00 mm Hg
Vapor Pressure 0.000143 mmHg @ 25.00 °C. (est)
Flash Point 255.00 °F. TCC ( 123.70 °C. ) (est)
logP (o/w) 1.168 (est)
Soluble in ethyl alcohol, 1:1 in 50% alcohol
Stability no special storage precautions necessary

Cosmetic Information

CosIngcosmetic data
Cosmetic Usesperfuming agents

Organoleptic Properties

Odor Strength medium
Substantivity 337 hour(s) at 10.00 % in dipropylene glycol
Odor Description
at 100.00 %.
Spicy, phenolic and balsamic with a creamy vanilla-like nuance
Odor sample from Givaudan Corporation
Taste Description at 80.00 ppm.

Safety Information

Preferred SDSView
Oral/Parenteral Toxicityoral-rat LD50 2580 mg/kg
Dermal Toxicityskin-rabbit LD50 > 5000 mg/kg
Inhalation ToxicityNot determined

GHS Classification

['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']

Safety in Use

Categoryflavor and fragrance agents
RIFM Fragrance Material Safety AssessmentSearch
Recommendation for zingerone usage levels up to2.0000 % 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)
baked goods-
beverages(nonalcoholic)-
beverages(alcoholic)-
breakfast cereal-
cheese-
chewing gum-
condiments / relishes-
confectionery froastings-
egg products-
fats / oils-
fish products-
frozen dairy-
fruit ices-
gelatins / puddings-
granulated sugar-
gravies-
hard candy-
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-

Advanced Biotech. Inc.

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Beijing Lys Chemicals Co, LTD.

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Berje Inc.

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Lluch Essence S.L.

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M&U International LLC

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Penta International Corporation

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Synerzine, Inc.

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Synerzine is a leading supplier of flavor and fragrance ingredients.

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TCI AMERICA

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Tianjin Danjun International Trade Co., LTD.

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R C Treatt and Co Ltd

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Ernesto Ventós S.A.

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Vigon International

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WholeChem, LLC

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Potential Uses

FR allspice FR amber FR balsam FR butterscotch FR cassia FR christmas FR coconut FL cookie FR florida breeze FR gardenia FR ginger FL ginger ale FR ginger white ginger FR gingerbread FR herbal FR jasmin FR lychee modifier FR moss FR oriental FR pumpkin pie FR raspberry FR saffron FL/FR snake root FR spice FL tropical FR vanilla FR woody

Natural Occurrence

cranberry fruit ginger oil ginger rhizome ginger rhizome oil ginger root ginger root oil ginger root oil CO2 extract @ 2.26% Data oregano shoot origanum onites shoot raspberry red raspberry fruit

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