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CAS Number: 4525-33-1
EC Number: 224-859-8
E number: E242 (preservatives)
APPLICATIONS
E242 (Dimethyl dicarbonate) (DMDC) is used as a cold sterilization agent for soft drinks and wines.
It has a broad antimicrobial range of action against yeasts, mould fungi, and bacteria.
E242 (Dimethyl dicarbonate) is unstable in aqueous solution and breaks down almost immediately after addition to beverages.
The principal breakdown products in wine and aqueous liquids are methanol and carbon dioxide.
Dimethylcarbonate (DMC) and methyl ethyl carbonate (MEC), as well as carbomethoxy adducts of amines, sugars, and fruit acids, are also formed in minor amounts.
In the presence of trace quantities of ammonia or ammonium ions (e.g. in wines), E242 (Dimethyl dicarbonate) forms trace quantities of methylcarbamate(MC).
E242 (Dimethyl dicarbonate) is an Antimicrobial agent effective for producing pathogen-free apple cider.
Also E242 (Dimethyl dicarbonate) is useful for killing yeast (but not acetogenic bacteria) in wine before bottling.
E242 (Dimethyl dicarbonate) is a synthetic preservative used mostly as a beverage preservative.
The packaged food industry is witnessing steady growth owing to which substantial growth is being witnessed in the food preservation industry.
E242 (Dimethyl dicarbonate) is used in wines as it inhibits the growth of wine spoilage yeasts.
Due to its versatile nature, E242 (Dimethyl dicarbonate) also finds applications in non-alcoholic beverages where it is used to stabilize carbonated or non-carbonated beverages, such as iced tea and flavored water.
E242 (Dimethyl dicarbonate) is easily available and is thus, relatively inexpensive.
E242 (Dimethyl dicarbonate) penetrates cells and deactivates enzymes, leading to the destruction of microorganisms.
When added to a beverage, E242 (Dimethyl dicarbonate) rapidly breaks down into negligible amounts of methanol and carbon dioxide -- two naturally occurring compounds in many beverages, such as fruit and vegetable juices and wines.
E242 (Dimethyl dicarbonate) has no effect on the taste, smell or colour of the beverage.
E242 (Dimethyl dicarbonate) is suitable for carbonated or non-carbonated juice beverages, isotonic sports beverages, iced teas and flavored water and wines.
E242 (Dimethyl dicarbonate) can permeate through the cell membrane, and block the metabolism through reacting with the enzymes of microorganism, then achieve the purpose of sterilization.
Even in very low additive amount, E242 (Dimethyl dicarbonate) can effectively kill typical spoilage bacteria in beverage, and not affect the taste, flavor and color of the beverage.
Furthermore, E242 (Dimethyl dicarbonate) could be rapidly and completely hydrolyzed to carbon dioxide and methanol, which are the natural ingredients of juice.
E242 (Dimethyl dicarbonate) is an intermediate used in the synthesis of SR13668 which is designed to mimic the unique anticancer mechanisms of dietary indole-3-carbinol to block Akt signaling.
E242 (Dimethyl dicarbonate) (DMDC), a chemical used to combat brettanomyces in wine, is classified as an additive.
E242 (Dimethyl dicarbonate) is allowed for the preservation of nonalcoholic flavored drinks, alcohol-free wine, and liquid-tea concentrate in ingoing amounts up to 250 mg/L.
Because of its reactivity to nucleophilic groups present in proteins, it easily binds to these, which, in the case of enzymes, leads to inactivation of these and hence to inactivation of microorganisms.
In an aqueous medium, it undergoes complete hydrolysis to methanol and carbon dioxide within a few hours.
The EC Directive provides a remark that E242 (Dimethyl dicarbonate) residues are not detectable in drinks.
E242 (Dimethyl dicarbonate) is primarily used as a beverage preservative, processing aid, or sterilant (E number 242).
The application of E242 (Dimethyl dicarbonate) (DMDC) is particularly useful when wine needs to be sterilized but cannot be sterile filtered, pasteurized, or sulfured.
E242 (Dimethyl dicarbonate) is also used to stabilize non-alcoholic beverages such as carbonated or non-carbonated juice beverages, isotonic sports beverages, iced teas, and flavored waters.
E242 (Dimethyl dicarbonate) is added before the filling of the beverage.
E242 (Dimethyl dicarbonate) then breaks down into small amounts of methanol and carbon dioxide, which are both natural constituents of fruit and vegetable juices.
The market is segmented by Type Food Grade E242 (Dimethyl dicarbonate), Industrial Grade DMDC and By Application Feed Antioxidant, Food Preservative, PVC Stabilizer.
USE IN WINE
In wine, E242 (Dimethyl dicarbonate) is often used to replace potassium sorbate, as it inactivates wine spoilage yeasts such as Brettanomyces.
Once E242 (Dimethyl dicarbonate) has been added to beverages, the efficacy of the chemical is provided by the following reactions:
E242 (Dimethyl dicarbonate) + water → methanol + carbon dioxide
E242 (Dimethyl dicarbonate) + ethanol → ethyl methyl carbonate
E242 (Dimethyl dicarbonate) + ammonia → methyl carbamate
E242 (Dimethyl dicarbonate) + amino acid → derived carboxymethyl
The application of E242 (Dimethyl dicarbonate) is particularly useful when wine needs to be sterilized but cannot be sterile filtered, pasteurized, or sulfured.
E242 (Dimethyl dicarbonate) is also used to stabilize non-alcoholic beverages such as carbonated or non-carbonated juice beverages, isotonic sports beverages, iced teas and flavored waters.
E242 (Dimethyl dicarbonate) is added before the filling of the beverage.
E242 (Dimethyl dicarbonate) then breaks down into small amounts of methanol and carbon dioxide, which are both natural constituents of fruit and vegetable juices.
The EU Scientific Committee on Food, the FDA in the United States and the JECFA of the WHO have confirmed the safe use in beverages.
The FDA approved its use in wines in 1988, with the maximum level being permitted set at 200 mg/L, and only if there were fewer than 500 yeast cells/mL at time of dosage.
E242 (Dimethyl dicarbonate) is also approved in the EU, where it is listed under E number E242, as well as Australia and New Zealand.
E242 (Dimethyl dicarbonate) is sometimes used as a preservative in wine as a replacement to sulfur dioxide, inactivating wine spoilage yeasts such as Brettanomyces.
In the U.S. the FDA approved its use in wines in 1998, with the maximum permitted level being set at 200mg/L, and only if there was less than 500 yeast cells/mL at time of dosage.
Usage has also been approved in Germany (since 1978) and New Zealand.
The application of E242 (Dimethyl dicarbonate) is particularly useful when wine needs to be sterilised but cannot be sterile filtered, pasteurized, or sulfured.
E242 (Dimethyl dicarbonate) has also been used to sterilise coffee, tea, cider, fruit wine and mead.
DESCRIPTION
E242 (Dimethyl dicarbonate) (DMDC) is an organic compound which is a colorless liquid with a pungent odor at high concentration at room temperature.
E242 (Dimethyl dicarbonate) is primarily used as a beverage preservative, processing aid, or sterilant (INS No. 242), and acts by inhibiting the enzymes acetate kinase and L-glutamic acid decarboxylase.
It has also been proposed that E242 (Dimethyl dicarbonate) inhibits the enzymes alcohol dehydrogenase and glyceraldehyde 3-phosphate dehydrogenase by causing the methoxycarbonylation of their histidine components.
E242 (Dimethyl dicarbonate) or DMDC is a colourless liquid with a sharp odour.
E242 (Dimethyl dicarbonate) is an antimicrobial agent which can legally be used in wine in Australia and New Zealand at rates up to 200 mg/L.
E242 (Dimethyl dicarbonate) works by binding with particular amino acid residues located at the catalytic centre of key cellular enzymes, particularly alcohol dehydrogenase and glyceraldehyde-3-phosphate dehydrogenase, deactivating them.
With these enzymes deactivated, glycolysis, which is required for energy production, cannot continue, so the cell dies.
The action of E242 (Dimethyl dicarbonate) against microorganisms in wine is rapid; however, it quickly hydrolyses to mainly methanol and carbon dioxide (within 1 hour at 30°C and within 5 hours at 10°C), so should be added to wine in as pure a form as possible.
Consequently, to be most effective at ensuring wine sterility, E242 (Dimethyl dicarbonate) should be added just before the filler bowl in the bottling sequence.
In addition, DMDC must be thoroughly mixed to ensure homogenisation through the wine.
E242 (Dimethyl dicarbonate) is an irritant, acutely toxic, corrosive and flammable.
Because E242 (Dimethyl dicarbonate) is corrosive to skin and eyes and toxic by inhalation and ingestion, certain safety precautions must be taken when handling concentrated DMDC.
This includes hand protection, eye protection, skin protection and a respirator if ventilation is inadequate.
Detailed precautions for safe handling, conditions for safe storage and first aid measures are given in the product Safety Data Sheet available from suppliers.
Due to its rapid hydrolysis, the need for accurate and homogeneous mixing through the wine, combined with its safety issues, E242 (Dimethyl dicarbonate) needs to be added to wine using a metered dosing system.
Such a dosing system should ensure that the addition of E242 (Dimethyl dicarbonate) is well controlled in a way that is consistent with good manufacturing practice.
E242 (Dimethyl dicarbonate), DMDC, has a molecular formula C4H6O5 and a molar mass of 134.09 g/mol.
E242 (Dimethyl dicarbonate) is soluble in water and miscible in toluene (JECFA).
And, E242 (Dimethyl dicarbonate) is currently used as a preservative in food with antimicrobial action.
In 1988, E242 (Dimethyl dicarbonate) was approved by the FDA for use as an antimicrobial agent in wines.
The FDA approved its use in concentration levels not to exceed 200 ppm and only when yeast cell counts are below 500 cells/ mL.
E242 (Dimethyl dicarbonate) is classified as a “processing aid”, not a chemical preservative, by the FDA so it can be used in food processing without being listed on the ingredients.
In aqueous solution it undergoes rapid hydrolysis to yield naturally present levels of methanol and CO2.
E242 (Dimethyl dicarbonate) (DMDC), also known as Viguolin, is a kind of fruit juice beverage preservative.
Under normal or even low temperature conditions, E242 (Dimethyl dicarbonate) has a strong ability to kill many contaminating bacteria in fruit juice drinks, and its antiseptic effect is closely related to the modification and inactivation of key enzyme proteins in the bacteria by DMDC.
Compared with other physical sterilization technologies, the use of E242 (Dimethyl dicarbonate) is low in cost, simple and safe to operate, and does not affect the taste, smell and color of the product.
E242 (Dimethyl dicarbonate) has become one of the hotspots in the research of emerging non-thermal sterilization technologies.
PROPERTIES
Chemical formula: C4H6O5
Molar mass: 134.087 g·mol−1
Appearance: Colorless liquid
Density: 1.25 g/mL
Melting point: 16 to 18 °C (61 to 64 °F; 289 to 291 K)
Boiling point: 172 °C (342 °F; 445 K)
Viscosity: 2.1 Pa·s (20 °C)
STANDARDS FOR USE
E242 (Dimethyl dicarbonate) is not permitted to use for food products other than fruit wines and nonalcoholic beverages (excluding mineral waters).
The amount of E242 (Dimethyl dicarbonate) shall not be exceeding 0.25 g/kg in fruit wines (excluding grape wine) and nonalcoholic beverages, and not be exceeding 0.20 g/kg in grape wine.
MECHANISM OF ACTION
E242 (Dimethyl dicarbonate) has been approved by FDA for use as a yeast inhibitor in bottled wines ( FR Oct. 21 , 1988 ).
E242 (Dimethyl dicarbonate) 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.
SYNONYMS
DMDC
Dicarbonic acid dimethyl ester
Dimethyl pyrocarbonate
Velcorin
4525-33-1
Carbonic acid, methoxycarbonyl methyl ester
Pyrocarbonic acid dimethyl ester
