Dimethyl dicarbonate

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Dimethyl dicarbonate
Skeletal formula of dimethyl dicarbonate
Dimethyl-dicarbonate-3D-balls.png
Names
IUPAC name
methoxycarbonyl methyl carbonate
Other names
DMDC; Dicarbonic acid dimethyl ester; Dimethyl pyrocarbonate; Velcorin
Identifiers
4525-33-1 YesY
ChemSpider 2976 YesY
Jmol-3D images Image
Image
PubChem 3086
Properties
C4H6O5
Molar mass 134.09 g·mol−1
Appearance Colorless liquid
Density 1.25 g/mL
Melting point 16 °C (61 °F; 289 K)
Boiling point 172 °C (342 °F; 445 K)
Viscosity 2.1 Pa·s (20 °C)
Hazards
Main hazards Toxic
R-phrases R22 R23 R34
S-phrases S7/9 S26 S36/37/39 S45
Related compounds
Related compounds
Di-tert-butyl dicarbonate
diethylpyrocarbonate
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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Infobox references

Dimethyl dicarbonate (DMDC) is an organic compound which is a colorless liquid with a sharp odor at room temperature. It 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.[1] It has also been proposed that DMDC inhibits the enzymes alcohol dehydrogenase and glyceraldehyde 3-phosphate dehydrogenase by causing the methoxycarbonylation of their histidine components.[2]

Use in wine[edit]

In wine, it is often used to replace potassium sorbate, as it inactivates wine spoilage yeasts such as Brettanomyces. Once it has been added to beverages, the efficacy of the chemical is provided by the following reactions:

DMDC + H2O → 2 CH3OH + 2 CO2
DMDC + Ethanol → Ethyl methyl carbonate
DMDC + NH3 → Methyl carbamate
DMDC + Amino acid → Derived carboxymethyl

The application of DMDC is particularly useful when wine needs to be sterilized but cannot be sterile filtered, pasteurized, 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 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.[3] It is also approved in the EU, where it is listed under E number E242,[4] as well as Australia and New Zealand.[5]

References[edit]

  1. ^ [1][dead link]
  2. ^ DMDC's role in bottle stability - dimethyl dicarbonate, Wines & Vines, Oct 1990
  3. ^ US Food and Drug Administration: "Listing of Food Additives Status Part I". Retrieved 2011-10-27. 
  4. ^ UK Food Standards Agency: "Current EU approved additives and their E Numbers". Retrieved 2011-10-27. 
  5. ^ Food Standards Australia and New Zealand, Application A1015 - Classification of Dimethyl Dicarbonate - Approval Report -15 December 2010"Application A1025 - Classification of Dimethyl Dicarbonate". Retrieved 2010-12-15. 

External links[edit]