4525-33-1 Usage
Description
Dimethyl dicarbonate (DMDC), also known as Viguolin, is a fruit juice beverage preservative (INS No. 242) that is permitted for use in food additive standards. It possesses a strong ability to eliminate various contaminating bacteria in fruit juice drinks under normal or even low temperature conditions. The antiseptic effect of DMDC is attributed to its modification and inactivation of key enzyme proteins in bacteria. Compared to other physical sterilization technologies, DMDC is cost-effective, easy to use, and safe, without affecting the taste, smell, or color of the product. It has become a prominent research focus in emerging non-thermal sterilization technologies.
Uses
Used in Beverage Industry:
DIMETHYL DICARBONATE is used as a microbial control agent for preserving the quality and safety of fruit juice drinks, nonalcoholic flavored drinks, alcohol-free wine, and liquid-tea concentrate. It is effective against a broad spectrum of microorganisms, including various yeasts and bacteria species.
DIMETHYL DICARBONATE is used as an antimicrobial agent for combating brettanomyces in wine, ensuring the product's stability and preventing spoilage. It is classified as an additive and is allowed for use in ingoing amounts up to 250 mg/L.
DIMETHYL DICARBONATE is used for inactivating microorganisms by deactivating their enzymes, primarily through reaction with protein imidazole and amine groups. This leads to the destruction of the microorganisms, maintaining the quality and safety of the beverages.
DIMETHYL DICARBONATE is used in nonjuice-containing beverages and carbonated, dilute beverages containing juice, fruit flavor, or both, with the juice content not exceeding 50%. Its effectiveness is based on the hydrolysis rate, which occurs when DMDC reacts with water. The rate of hydrolysis is dependent on the temperature of the beverage or wine, taking about four hours at 10°C (50°F) or two hours at 20°C (68°F) for complete breakdown.
DIMETHYL DICARBONATE is used in wine and other beverages to ensure that the remaining unreacted DMDC breaks down rapidly into methanol and carbon dioxide, complying with the EC Directive that states dimethyl dicarbonate residues are not detectable in drinks. This ensures the safety and quality of the final product.
Mechanism of action
Dimethyl dicarbonate has been approved by FDA for use as a yeast inhibitor in bottled wines ( FR Oct. 21 , 1988 ) .It is highly reactive and can react chemically with a variety of reactive groups (such as sulfhydryl, hydroxyl, amino and carboxyl). Among them, the researchers focused on the characteristics of the reaction between pyrocarbonate compounds and enzyme proteins. The results show that in the reaction between enzyme protein and pyrocarbonate compounds, the imidazole group in histidine residues in the enzyme protein is mainly involved in the reaction to form methyl (or ethyl) oxyformyl imidazole group. In addition, studies have also found that many enzymes (such as bovine brain tissue succinate semialdehyde reductase, nucleic acid hydrolase, alcohol dehydrogenase, etc.) have been modified by pyrocarbonate compounds, their enzyme activity has been significantly reduced, and the enzyme activity has decreased and the enzyme activity has decreased. The degree of histidine modification in the protein has a significant correlation.
Preparation
In a 2000ml reaction flask, add 400g methyl chloroformate (industrial grade), 400ml dichloromethane, add 143.82g dodecyldimethylbenzylammonium chloride, stir and cool to 5-15°C, Add 1166gl 4% sodium hydroxide aqueous solution dropwise. After the addition is complete, let stand for layering. Discard the water layer. Add 32g 85% sulfuric acid to the organic layer. Stir for 1.5 hours at room temperature. Separate the layers. Add anhydrous magnesium sulfate to dry the organic layer and filter. , Then vacuum distillation, first remove the solvent, and then collect the 200Pa, 30°C -35°C distillate to obtain 232g of colorless liquid product dimethyl dicarbonate, yield 81.9%, freezing point 17°C, GC purity 99.9%.
Safety Profile
Dimethyl dicarbonate (Velcorinor DMDC) is now used as a preservative in many countries but its toxicity requires the use of special dispensing equipment. Dimethyl dicarbonate decom-poses to CHgOH and CO2 in a product and its maximum rate of addition is typi-cally 0.025 wt%.DMDC is used in the beverage industry for supplemental microbial control in beverages during the final stages of filling. It is added to beverages, whose viable microorganism load was previously reduced by other technologies, immediately prior to bottling, canning, or other forms of final packaging. To ensure its safe use, the agency set the maximum amount of DMDC that may be added to food at 250 parts per million (ppm). DMDC is currently approved under §?172.133(b)(1) and (b)(2) as an inhibitor of yeast in various beverages under normal circumstances of bottling or canning where the viable yeast count has been reduced to 500 per milliliter (mL) or less by current good manufacturing practices. DMDC is also approved under §?172.133(b)(3) and (b)(4) as an inhibitor of yeast in additional beverages. During its review of the subject petition, FDA found that restrictions given in paragraphs (b)(1) and (b)(2) were inadvertently omitted from paragraphs (b)(3) and (b)(4).https://www.federalregister.gov/documents/2001/03/07/01-5511/food-additives-permitted-for-direct-addition-to-food-for-human-consumption-dimethyl-dicarbonate
Purification Methods
Dissolve it in Et2O, shake this with a small volume of 0.1N HCl, dry Et2O with Na2SO4 and distil in in vacuo below 100o to give a clear liquid. It decomposes to CO2 and dimethyl carbonate on heating at 123-149o. It is readily hydrolysed by H2O and is a yeast inhibitor and an IRRITANT. [Brysov et al. J Org Chem USSR 10 2551 1974, Boehm & Mehta Chem Ber 71 1797 1938, Beilstein 3 IV 17.]
Check Digit Verification of cas no
The CAS Registry Mumber 4525-33-1 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 4,5,2 and 5 respectively; the second part has 2 digits, 3 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 4525-33:
(6*4)+(5*5)+(4*2)+(3*5)+(2*3)+(1*3)=81
81 % 10 = 1
So 4525-33-1 is a valid CAS Registry Number.
InChI:InChI=1/C4H6O5/c1-7-3(5)9-4(6)8-2/h1-2H3
4525-33-1Relevant articles and documents
Howe,Morris
, p. 1901 (1962)
Process For Preparing Dialkyl Dicarbonates
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Page/Page column 2, (2008/06/13)
The novel process for preparing dialkyl dicarbonates by reacting the corresponding alkyl haloformates with alkali metal hydroxides, alkaline earth metal hydroxides and/or carbonates in the presence of water-immiscible organic solvents and in the presence of a catalyst is characterized in that the catalyst used is at least one tertiary alkylamine of the formula (I) [in-line-formulae]NR1R2R3 ??(I), [/in-line-formulae] where the substituents are each as defined in the description.