122-48-5 Usage
Description
Vanillylacetone, also known as 4-hydroxy-3-methoxyphenylbutan-2-one, is a phenolic compound that is naturally found in various plants, including cranberry, ginger, raspberry, and mango. It is characterized by its strong, pungent odor reminiscent of ginger and has a sharp taste, similar to ginger. Vanillylacetone is a white solid that is soluble in ether, sparingly soluble in water, and petroleum ether.
Uses
Used in Pharmaceutical Applications:
Vanillylacetone is used as a cytotoxic, cytoprotective, and antioxidant agent for its variable activity against liver and human tumor cells. It is also utilized in herbal medicine for various purposes due to its beneficial properties.
Used in Flavor and Fragrance Industry:
Vanillylacetone is used as a flavoring agent in artificial spice oils, contributing to its spicy, sweet, and creamy taste characteristics. It is also employed in the fragrance industry for its low-impact, creamy, spicy eugenol clove-like aroma with a slight balsamic and vanilla-like note.
Used in Cosmetics Industry:
Vanillylacetone is used in the cosmetics industry for its unique scent and flavor properties, enhancing the sensory experience of various cosmetic products.
Taste and Aroma Threshold Values:
At 80 ppm, Vanillylacetone has a spicy taste with a biting, lingering heat. In a 5% sugar solution at 20 ppm, it exhibits a smooth, sweet, creamy, and warm taste, with spicy clove and a slight lingering burning bite. At 10.0%, its aroma is characterized as low impacting, creamy, spicy eugenol clove-like with a slight balsamic and vanilla-like note.
Occurrence:
Vanillylacetone is reported to be found in the essential oil of Zingiber officinale (ginger) and is also found in cranberry, raspberry, ginger, and mango.
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.
Preparation
By condensation of vanillin with acetone followed by hydrogenation.
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-
GINGEROL DERIVATIVE HAVING INHIBITORY ACTIVITY AGAINST BIOFILM FORMATION AND PHARMACEUTICAL COMPOSITION COMPRISING SAME AS EFFECTIVE INGREDIENT FOR PREVENTING OR TREATING BIOFILM-CAUSED INFECTION SYMPTOM
-
, (2020/09/22)
The present invention relates to a gingerol derivative having inhibitory activity against biofilm formation and a pharmaceutical composition for preventing or treating infections caused by biofilms including the gingerol derivative as an active ingredient. The gingerol derivative of the present invention exhibits significantly improved binding affinity for LasR and inhibitory activity against biofilm formation. Therefore, the gingerol derivative of the present invention can act on various membrane surfaces where biofilms tend to form and can effectively inhibit the formation of the corresponding biofilms. In addition, the use of the pharmaceutical composition according to the present invention can fundamentally prevent or treat a variety of infections caused by biofilms due to the presence of the gingerol derivative in the pharmaceutical composition.
Discovery and Characterization of Pure RhlR Antagonists against Pseudomonas aeruginosa Infections
Nam, SangJin,Ham, So-Young,Kwon, Hongmok,Kim, Han-Shin,Moon, Suhyun,Lee, Jeong-Hoon,Lim, Taehyeong,Son, Sang-Hyun,Park, Hee-Deung,Byun, Youngjoo
, p. 8388 - 8407 (2020/09/21)
Pseudomonas aeruginosa (P. aeruginosa) is an opportunistic human pathogen that forms biofilms and produces virulence factors via quorum sensing (QS). Blocking the QS system in P. aeruginosa is an excellent strategy to reduce biofilm formation and the production of virulence factors. RhlR plays an essential role in the QS system of P. aeruginosa. We synthesized 55 analogues based on the chemical structure of 4-gingerol and evaluated their RhlR inhibitory activities using the cell-based reporter strain assay. Comprehensive structure-activity relationship studies identified the alkynyl ketone 30 as the most potent RhlR antagonist. This compound displayed selective RhlR antagonism over LasR and PqsR, strong inhibition of biofilm formation, and reduced production of virulence factors in P. aeruginosa. Furthermore, the survival rate of Tenebrio molitor larvae treated with 30 in vivo greatly improved. Therefore, compound 30, a pure RhlR antagonist, can be utilized for developing QS-modulating molecules in the control of P. aeruginosa infections.