Vanillylacetone

Vanillylacetone Basic information
Food flavorings Content Analysis Toxicity Limited use
Product Name:Vanillylacetone
Synonyms:(0)-paradol;[0]-Paradol;3-Methoxy-4-hydroxybenzylacetone;3-methoxy-4-hydroxy-benzylacetone;4-(3-methoxy-4-hydroxyphenyl)-2-butanone;4-(4-hydroxy-3;4-(4-hydroxy-3-methoxyphenyl)-2-butanon;Gingerone
CAS:122-48-5
MF:C11H14O3
MW:194.23
EINECS:204-548-3
Product Categories:chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract;Inhibitors;Miscellaneous Natural Products
Mol File:122-48-5.mol
Vanillylacetone Structure
Vanillylacetone Chemical Properties
Melting point 40-41 °C(lit.)
Boiling point 141 °C0.5 mm Hg(lit.)
density 1.14 g/mL at 25 °C(lit.)
FEMA 3124 | ZINGERONE
refractive index n20/D 1.541(lit.)
Fp >230 °F
storage temp. Sealed in dry,2-8°C
solubility Acetonitrile (Slightly), DMSO (Slightly), Methanol (Slightly)
form Solid
pka10.03±0.20(Predicted)
color White to Pale Yellow
Odorat 100.00 %. sweet spicy phenolic ginger vanilla woody
Odor Typespicy
Merck 14,10166
JECFA Number730
InChIKeyOJYLAHXKWMRDGS-UHFFFAOYSA-N
LogP0.64
CAS DataBase Reference122-48-5(CAS DataBase Reference)
NIST Chemistry Reference2-Butanone, 4-(4-hydroxy-3-methoxyphenyl)-(122-48-5)
EPA Substance Registry System2-Butanone, 4-(4-hydroxy-3-methoxyphenyl)- (122-48-5)
Safety Information
Risk Statements 36/37/38
Safety Statements 26-36
WGK Germany 2
RTECS EL8900000
TSCA Yes
HS Code 29333999
Hazardous Substances Data122-48-5(Hazardous Substances Data)
MSDS Information
ProviderLanguage
4-(4-Hydroxy-3-methoxyphenyl)butan-2-one English
SigmaAldrich English
ALFA English
Vanillylacetone Usage And Synthesis
Food flavoringsVanillylacetone also called zingerone , is a food spice which is allowed to be prepared   appropriately according to production needs by Chinese "Sanitary Standards of Using Food Additives" (GB 2760-1996),its chemical name is 4-(4-hydroxy 3-methoxyphenyl)-2-butanone. Yellow or light amber crystal (acetone, petroleum ether or ethyl ether-petroleum ether), at room temperature, after long time ,it becomes to a viscous liquid.It  has a strong irritating odor like spicy ginger and ginger-like pungent taste,it has a sweet, spicy, full-bodied and deep floral aroma, fragrance lasts for a long time. The relative density is 1.138~1.139 (25 ℃), melting point 40~41 ℃, boiling point 290 ℃ (102 ℃), refractive index 1.544~1.545. It  can be dissolved in 50% ethanol in 1:1 ratio , slightly soluble in water and petroleum ether, soluble in dilute alkali. In the steam it slowly evaporates. When heated ,it can deoxidate silver nitrate ammonia solution; and it can react with an alcohol solution of ferric chloride to turn to green. It is derived from the Zingiber officinale essential oils , Vanillylacetone is the main constituent of ginger oil . After the condensation reaction of vanillin and acetone,it is obtained through hydrogenation .it is used as a full-bodied flavor sweeteners and edible flavorings. In the perfumed products ,it can have a "leather", "tobacco" flavor. It is not easy to change color.
Vanillylacetone can be used in the formulation of flavors, it is mainly used as sweeteners for rich aromas and flavors , in very small quantities, the application range is very small. IFRA has no restrictions.
Vanillylacetone is recognized as GRAS by FEMA , FEMA number is 3124, and it is  approved by the FDA for human consumption,it is included in the artificial flavor table by the Council of Europe in the level of 15mg/kg dosage which can be used in foods and is not harmful to human health . Vanillylacetone can be used for food flavor and seasoning product formulations.
FEMA provides: Vanillylacetone highest reference amount is  soft drinks, 6.9mg/kg; ice cream, ices, 7.8mg/kg; candy, 11mg/kg; baked goods, 11mg/kg; chewing gum, 15mg/kg.


Content AnalysisUse gas chromatography (GT-10-4) nonpolar column method for the determination.
ToxicityGRAS (FEMA).
LD502.58g/kg (rat, dictation).
Limited useFEMA (mg/kg): Soft drinks 6.9; cold:7.8 ; confectionery, bakery products, 11.0; Chewing Gum:15.0
FDA, §172.515: the right amount limit.
Chemical PropertiesWhite solid. Soluble in ether; sparingly soluble in water and petroleum ether.
Chemical PropertiesZingerone has a strong, pungent odor reminiscent of ginger. It has a sharp taste, similar to ginger.
OccurrenceReported found in the essential oil of Zingiber officinale. Also reported found in cranberry, raspberry, ginger and mango.
UsesVanillylacetone is a phenolic compound that naturally occurs in cranberry and ginger. Studies shows that Vanillylacetone exhibits variable cytotoxic, cytoprotective and antioxidant activity against liver and human tumor cells. Vanillylacetone is also used in herbal medicine for various purposes.
UsesVanillylacetone is a phenolic compound that naturally occurs in cranberry and ginger. Studies shows that Vanillylacetone exhibits variable cytotoxic, cytoprotective and antioxidant activity against li ver and human tumor cells. Vanillylacetone is also used in herbal medicine for various purposes.
UsesIn fragrances, flavors and cosmetics; in artificial spice oils.
DefinitionChEBI: A ketone that is 4-phenylbutan-2-one in which the phenyl ring is substituted at positions 3 and 4 by methoxy and hydroxy groups respectively. The major pungent component in ginger.
PreparationBy condensation of vanillin with acetone followed by hydrogenation.
Aroma threshold valuesAroma characteristics at 10.0%: low impacting, creamy, spicy eugenol clove-like with a slight balsamic vanilla-like note.
Taste threshold valuesTaste characteristics at 80 ppm: spicy with a biting, lingering heat. Taste characteristics at 20 ppm in 5% sugar solution: smooth, sweet, creamy and warm, spicy clove with a slight lingering burning bite.
Safety ProfileModerately toxic by ingestion. A skin irritant. A flammable liquid. When heated to decomposition it emits acrid smoke and irritating fumes.
Piperonyl acetone HOMOERIODICTYOL 2,9-DIAZA-10-BENZO[D]1,3-DIOXOLEN-5-YL-14,14-DIMETHYL-12-OXOTRICYCLO[9.4.0.0(3,8)]PENTADECA-1(11),3(8),4,6-TETRAENE-5-CARBOXYLIC ACID 2,10-DIAZA-9-(4-HYDROXY-3,5-DIMETHOXYPHENYL)-5,5,13-TRIMETHYLTRICYCLO[9.4.0.0(3,8)]PENTADECA-1(15),3(8),11(12),13-TETRAEN-7-ONE 6,7-Dimethoxy-2-tetralone 5-[3,4(METHYLENEDIOXY)PHENYL]-1,3-CYCLOHEXANEDIONE 2,10-DIAZA-9-(4-HYDROXY-3,5-DIMETHOXYPHENYL)-5,5-DIMETHYLTRICYCLO[9.4.0.0(3,8)]PENTADECA-1(11),3(8),12,14-TETRAEN-7-ONE 5,7-DIHYDROXY-3',4',5'-TRIMETHOXYFLAVANONE 2',4',6'-TRIHYDROXY-3,4-METHYLENEDIOXYDIHYDROCHALCONE (Trifluoromethoxy)benzene TETRABENAZINE [3-(3,4-DIMETHOXYPHENYL)OXIRAN-2-YL](PHENYL)METHANONE [3-(1,3-BENZODIOXOL-5-YL)OXIRAN-2-YL](3,4-DIMETHOXYPHENYL)METHANONE 2',4',6'-TRIHYDROXY-3,4,5-TRIMETHOXYDIHYDROCHALCONE [2-(BENZYLOXY)PHENYL][3-(3,4,5-TRIMETHOXYPHENYL)OXIRAN-2-YL]METHANONE 2',4',6'-TRIHYDROXY-3,4-DIMETHOXYDIHYDROCHALCONE Vanillylacetone 1-(4-METHOXY-6-METHYL-5,6,7,8-TETRAHYDRO-[1,3]DIOXOLO[4,5-G]ISOQUINOLIN-5-YL)-PROPAN-2-ONE

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