Dimethyl dicarbonate (DMDC) is a colorless liquid with a pungent odor at high concentration at

room temperature Room temperature, colloquially, denotes the range of air temperatures most people find comfortable indoors while dressed in typical clothing. Comfortable temperatures can be extended beyond this range depending on humidity, air circulation, and ...

. It is primarily used as a

beverage A drink or beverage is a liquid intended for human consumption. In addition to their basic function of satisfying thirst, drinks play important roles in human culture. Common types of drinks include plain drinking water, milk, juice, smoothie ...

preservative A preservative is a substance or a chemical that is added to products such as food products, beverages, pharmaceutical drugs, paints, biological samples, cosmetics, wood, and many other products to prevent decomposition by microbial growth or ...

, processing aid, or sterilant ( INS No. 242) being highly active against typical beverage spoiling microorganisms like yeast, bacteria, or mould.

Usage

Dimethyl dicarbonate is used to stabilize beverages by preventing microbial spoilage. It can be used in various non-alcoholic as well as alcoholic drinks like wine, cider, beer-mix beverages or hard seltzers. Beverage spoiling microbes are killed by methoxycarbonylation of proteins. It acts by inhibiting

enzymes An enzyme () is a protein that acts as a biological catalyst by accelerating chemical reactions. The molecules upon which enzymes may act are called substrates, and the enzyme converts the substrates into different molecules known as pro ...

involved in the microbial metabolism, e.g. acetate kinase and

L-glutamic acid decarboxylase Glutamate decarboxylase or glutamic acid decarboxylase (GAD) is an enzyme that catalyzes the decarboxylation of glutamate to gamma-aminobutyric acid (GABA) and carbon dioxide (). GAD uses pyridoxal-phosphate (PLP) as a cofactor. The reaction pr ...

.
/ref> It has also been proposed that DMDC inhibits the enzymes

alcohol dehydrogenase Alcohol dehydrogenases (ADH) () are a group of dehydrogenase enzymes that occur in many organisms and facilitate the interconversion between alcohols and aldehydes or ketones with the reduction of nicotinamide adenine dinucleotide (NAD+) to N ...

and

glyceraldehyde 3-phosphate dehydrogenase Glyceraldehyde 3-phosphate dehydrogenase (abbreviated GAPDH) () is an enzyme of about 37kDa that catalyzes the sixth step of glycolysis and thus serves to break down glucose for energy and carbon molecules. In addition to this long establis ...

by causing the methoxycarbonylation of their

histidine Histidine (symbol His or H) is an essential amino acid that is used in the biosynthesis of proteins. It contains an Amine, α-amino group (which is in the protonated –NH3+ form under Physiological condition, biological conditions), a carboxylic ...

components.DMDC's role in bottle stability - dimethyl dicarbonate
, Wines & Vines, Oct 1990 In

wine Wine is an alcoholic drink made from Fermentation in winemaking, fermented fruit. Yeast in winemaking, Yeast consumes the sugar in the fruit and converts it to ethanol and carbon dioxide, releasing heat in the process. Wine is most often made f ...

, it is often used to replace

potassium sorbate Potassium sorbate is the potassium salt of sorbic acid, structural formula CH3CH=CH−CH=CH−CO2K. It is a white salt that is very soluble in water (58.2% at 20 °C). It is primarily used as a food preservative (E number 202). Potassium ...

, as it inactivates wine spoilage yeasts such as ''

Brettanomyces ''Brettanomyces'' is a non-spore forming genus of yeast in the family Saccharomycetaceae, and is often colloquially referred to as "Brett". The genus name ''Dekkera'' is used interchangeably with ''Brettanomyces'', as it describes the teleomor ...

''. Once it has been added to beverages, the efficacy of the chemical is provided by the following reactions: :DMDC + water → methanol + carbon dioxide :DMDC + ethanol → ethyl methyl carbonate :DMDC + ammonia → methyl carbamate :DMDC +

amino acid Amino acids are organic compounds that contain both amino and carboxylic acid functional groups. Although over 500 amino acids exist in nature, by far the most important are the 22 α-amino acids incorporated into proteins. Only these 22 a ...

→ derived carboxymethyl The application of DMDC is particularly useful when wine needs to be sterilized but cannot be sterile filtered,

pasteurized In food processing, pasteurization ( also pasteurisation) is a process of food preservation in which packaged foods (e.g., milk and fruit juices) are treated with mild heat, usually to less than , to eliminate pathogens and extend shelf life ...

, or sulfured. DMDC is also used to stabilize non-alcoholic beverages such as carbonated or non-carbonated juice beverages, isotonic sports beverages, iced teas and flavored waters. DMDC is added before the filling of the beverage. It then breaks down into small amounts of

methanol Methanol (also called methyl alcohol and wood spirit, amongst other names) is an organic chemical compound and the simplest aliphatic Alcohol (chemistry), alcohol, with the chemical formula (a methyl group linked to a hydroxyl group, often ab ...

and

carbon dioxide Carbon dioxide is a chemical compound with the chemical formula . It is made up of molecules that each have one carbon atom covalent bond, covalently double bonded to two oxygen atoms. It is found in a gas state at room temperature and at norma ...

, which are both natural constituents of fruit and vegetable juices. The EU

Scientific Committee on Food The Scientific Committee on Food (SCF), established in 1974, was the main committee providing the European Commission with scientific advice on food safety. "Scientific Committee on Food - FOOD STANDARDS AGENCY" (overview), Gov.uk, F ...

, the

FDA The United States Food and Drug Administration (FDA or US FDA) is a federal agency of the Department of Health and Human Services. The FDA is responsible for protecting and promoting public health through the control and supervision of food ...

in the United States and the JECFA of the WHO have confirmed the safe use in beverages. The

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. It is also approved in the EU, where it is listed under

E number E numbers, short for Europe numbers, are codes for substances used as food additives, including those found naturally in many foods, such as vitamin C, for use within the European Union (EU) and European Free Trade Association (EFTA). Commonly ...

E242, as well as Australia and New Zealand.Food Standards Australia and New Zealand, Application A1015 - Classification of Dimethyl Dicarbonate - Approval Report -15 December 2010

References

External links

Dimethyl dicarbonate at EPA SRSDimethyl dicarbonate and microbiological stability
{{DEFAULTSORT:Dimethyl Dicarbonate Winemaking Preservatives Methyl esters Methylating agents Dicarbonates E-number additives

Usage

See also

References

External links