Dimethyl dicarbonate

Dimethyl dicarbonate (DMDC) is a colorless liquid and a pungent odor at high concentration at room temperature. It is primarily used as a beverage preservative, processing aid, or sterilant (INS No. 242) being highly active against typical beverage spoiling microorganisms like yeast, bacteria, or mould.[1]

Dimethyl dicarbonate
Skeletal formula of dimethyl dicarbonate
Names
Preferred IUPAC name
Dimethyl dicarbonate
Other names
DMDC; Dicarbonic acid dimethyl ester; Dimethyl pyrocarbonate; Velcorin
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.022.601
EC Number
  • 224-859-8
E number E242 (preservatives)
UNII
  • InChI=1S/C4H6O5/c1-7-3(5)9-4(6)8-2/h1-2H3 checkY
    Key: GZDFHIJNHHMENY-UHFFFAOYSA-N checkY
  • InChI=1/C4H6O5/c1-7-3(5)9-4(6)8-2/h1-2H3
    Key: GZDFHIJNHHMENY-UHFFFAOYAQ
  • O=C(OC(=O)OC)OC
  • O=C(OC)OC(=O)OC
Properties
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)
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 Toxic
GHS labelling:
GHS02: FlammableGHS05: CorrosiveGHS06: ToxicGHS07: Exclamation mark
Danger
H226, H302, H312, H314, H330
P210, P233, P240, P241, P242, P243, P260, P264, P270, P271, P280, P284, P301+P312, P301+P330+P331, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P310, P312, P320, P321, P322, P330, P363, P370+P378, P403+P233, P403+P235, P405, P501
Related compounds
Related compounds
 Di-tert-butyl dicarbonate
diethylpyrocarbonate
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

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 involved in the microbial metabolism, e.g. acetate kinase and L-glutamic acid decarboxylase.[2] 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.[3]

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 + water → methanol + carbon dioxide
DMDC + ethanol → ethyl methyl carbonate
DMDC + ammonia → 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 produced by Lanxess under the trade name Velcorin®

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.[4] It is also approved in the EU, where it is listed under E number E242,[5] as well as Australia and New Zealand.[6]

See also

References
  1. Uhr, Hermann; Mielke, Burkhard; Exner, Otto; Payne, Ken R.; Hill, Edward (2013). "Biocides". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. pp. 1–26. doi:10.1002/14356007.a16_563.pub2.
  3. DMDC's role in bottle stability - dimethyl dicarbonate Archived 2015-09-24 at the Wayback Machine, Wines & Vines, Oct 1990
  4. US Food and Drug Administration: "Listing of Food Additives Status Part I". Food and Drug Administration. Archived from the original on 2013-03-14. Retrieved 2011-10-27.
  5. UK Food Standards Agency: "Current EU approved additives and their E Numbers". Retrieved 2011-10-27.
  6. 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.
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