Dimethyl dicarbonate

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Dimethyl dicarbonate
Skeletal formula of dimethyl dicarbonate
Dimethyl-dicarbonate-3D-balls.png
Identifiers
CAS number 4525-33-1 YesY
PubChem 3086
ChemSpider 2976 YesY
Jmol-3D images Image 1
Image 2
Properties
Molecular formula C4H6O5
Molar mass 134.09 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)
Hazards
R-phrases R22 R23 R34
S-phrases S7/9 S26 S36/37/39 S45
Main hazards Toxic
Related compounds
Related compounds Di-tert-butyl dicarbonate
diethylpyrocarbonate
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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Infobox references

Dimethyl dicarbonate (DMDC) is a colorless liquid with a sharp odor. Its primary use is as a beverage preservative and or 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 methoxycarbonylation of the histidine part of the enzymes alcohol dehydrogenase and glyceraldehyde 3-phosphate dehydrogenase by DMDC inhibits these essential enzymes also.[2] 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

DMDC 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 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]

The application of DMDC is particularly useful when wine needs to be sterilized but cannot be sterile filtered, pasteurized, or sulfured. DMDC is 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.

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]