122-48-5 Usage
Food flavorings
Vanillylacetone 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 Analysis
Use gas chromatography (GT-10-4) nonpolar column method for the determination.
Toxicity
GRAS (FEMA).
LD502.58g/kg (rat, dictation).
Limited use
FEMA (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 Properties
Different sources of media describe the Chemical Properties of 122-48-5 differently. You can refer to the following data:
1. White solid. Soluble in ether; sparingly soluble in water and petroleum ether.
2. Zingerone has a strong, pungent odor reminiscent of ginger. It has a sharp taste, similar to ginger.
Occurrence
Reported found in the essential oil of Zingiber officinale. Also reported found in cranberry, raspberry, ginger
and mango.
Uses
Different sources of media describe the Uses of 122-48-5 differently. You can refer to the following data:
1. Vanillylacetone 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.
2. Vanillylacetone 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.
3. In fragrances, flavors and cosmetics; in artificial spice oils.
Definition
ChEBI: 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.
Preparation
By condensation of vanillin with acetone followed by hydrogenation.
Aroma threshold values
Aroma characteristics at 10.0%: low impacting, creamy, spicy eugenol clove-like with a slight balsamic
vanilla-like note.
Taste threshold values
Taste 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 Profile
Moderately toxic by
ingestion. A skin irritant. A flammable
liquid. When heated to decomposition it
emits acrid smoke and irritating fumes.
Check Digit Verification of cas no
The CAS Registry Mumber 122-48-5 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,2 and 2 respectively; the second part has 2 digits, 4 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 122-48:
(5*1)+(4*2)+(3*2)+(2*4)+(1*8)=35
35 % 10 = 5
So 122-48-5 is a valid CAS Registry Number.
InChI:InChI=1/C11H14O3/c1-8(12)3-4-9-5-6-10(13)11(7-9)14-2/h5-7,13H,3-4H2,1-2H3
122-48-5Relevant articles and documents
A Hantzsch Amido Dihydropyridine as a Transfer Hydrogenation Reagent for α,β-Unsaturated Ketones
Van Arman, Scott A.,Zimmet, Austin J.,Murray, Ian E.
, p. 3528 - 3532 (2016)
An improved synthesis of the bis-methylamido Hantzsch dihydropyridine is described. The Hantzsch amide is demonstrated to be an effective transfer hydrogenation reagent using α,β-unsaturated ketones as the test case. Unreacted Hantzsch amide and the bis-methylamidopyridine byproduct are effectively removed by extraction in contrast to the commonly used Hantzsch diethyl ester. Several examples are given with the reaction being more effective for conjugated aromatic substrates than for aliphatics.
Reduction of solid-supported olefins and alkynes
Dickson, David P.,Toh, Christine,Lunda, Menaka,Yermolina, Maria V.,Wardrop, Duncan J.,Landrie, Chad L.
, p. 9535 - 9538 (2009)
(Chemical Equation Presented) The reduction of carbon-carbonmultiple bonds in alkynes and olefins supported on a polystyrene resin has been investigated. Homogeneous catalysis by titanocene reagents is effective for the stereoselective preparation of cis-
Chemoselective and metal-free reduction of α,β-unsaturated ketones by: In situ produced benzeneselenol from O -(tert -butyl) Se-phenyl selenocarbonate
Ballarotto, Marco,Siciliano, Carlo,Temperini, Andrea
, p. 33706 - 33717 (2020/10/22)
The carbon-carbon double bond of arylidene acetones and chalcones can be selectively reduced with benzeneselenol generated in situ by reacting O-(tert-butyl) Se-phenyl selenocarbonate with hydrochloric acid in ethanol. This mild, metal-free and experimentally simple reduction procedure displays considerable functional-group compatibility, products are obtained in good to excellent yields, and the use of toxic Se/CO mixture and NaSeH, or the smelly and air-sensitive benzeneselenol, is avoided. This journal is
Heterogeneous Catalytic Synthesis of Zingerone and Dehydrozingerone
Chistyakov, A. V.,Chistyakova, P. A.,Tsodikov, M. V.
, p. 1080 - 1086 (2020/10/02)
Abstract: Results of a single-stage heterogeneous catalytic synthesis of zingerone and dehydrozingerone have been described. The prospects of the proposed approach have been shown; the main kinetic laws governing the reaction have been revealed. Optimum conditions for zingerone and dehydrozingerone synthesis providing a yield of the target products of 45.8 and 76.2%, respectively, have been found.