Dimethyl dicarbonate

Last updated
Dimethyl dicarbonate
Dimethyl-dicarbonate-2D-skeletal.png
Dimethyl-dicarbonate-3D-balls.png
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 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 224-859-8
E number E242 (preservatives)
PubChem CID
UNII
  • InChI=1S/C4H6O5/c1-7-3(5)9-4(6)8-2/h1-2H3 Yes check.svgY
    Key: GZDFHIJNHHMENY-UHFFFAOYSA-N Yes check.svgY
  • 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
AppearanceColorless 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:
GHS-pictogram-flamme.svg GHS-pictogram-acid.svg GHS-pictogram-skull.svg GHS-pictogram-exclam.svg
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).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

Dimethyl dicarbonate (DMDC) is a colorless liquid with 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]

Contents

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

Related Research Articles

<span class="mw-page-title-main">Drink</span> Liquid intended for human consumption

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, smoothies and soft drinks. Traditionally warm beverages include coffee, tea, and hot chocolate. Caffeinated drinks that contain the stimulant caffeine have a long history.

<span class="mw-page-title-main">Denatured alcohol</span> Ethanol with additives to discourage recreational consumption

Denatured alcohol, also known as methylated spirits, metho, or meths in Australia, Ireland, New Zealand, South Africa, and the United Kingdom; and denatured rectified spirit is ethanol that has additives to make it poisonous, bad-tasting, foul-smelling, or nauseating to discourage its recreational consumption. It is sometimes dyed so that it can be identified visually. Pyridine and methanol, each and together, make denatured alcohol poisonous; and denatonium makes it bitter.

<span class="mw-page-title-main">Ginger ale</span> Soft drink flavoured with ginger

Ginger ale is a carbonated soft drink flavoured with ginger. It is consumed on its own or used as a mixer, often with spirit-based drinks. There are two main types of ginger ale. The golden style is credited to the Irish doctor Thomas Joseph Cantrell. The dry style, a paler drink with a much milder ginger flavour, was created by Canadian John McLaughlin.

<span class="mw-page-title-main">Acesulfame potassium</span> Calorie-free sugar substitute

Acesulfame potassium, also known as acesulfame K or Ace K, is a synthetic calorie-free sugar substitute often marketed under the trade names Sunett and Sweet One. In the European Union, it is known under the E number E950. It was discovered accidentally in 1967 by German chemist Karl Clauss at Hoechst AG. In chemical structure, acesulfame potassium is the potassium salt of 6-methyl-1,2,3-oxathiazine-4(3H)-one 2,2-dioxide. It is a white crystalline powder with molecular formula C
4
H
4
KNO
4
S
and a molecular weight of 201.24 g/mol.

<span class="mw-page-title-main">Ethyl carbamate</span> Chemical compound

Ethyl carbamate (also called urethane) is an organic compound with the formula CH3CH2OC(O)NH2. It is an ester of carbamic acid and a white solid. Despite its name, it is not a component of polyurethanes. Because it is a carcinogen, it is rarely used, but naturally forms in low quantities in many types of fermented foods and drinks.

<span class="mw-page-title-main">Winemaking</span> Production of wine

Winemaking, wine-making, or vinification is the production of wine, starting with the selection of the fruit, its fermentation into alcohol, and the bottling of the finished liquid. The history of wine-making stretches over millennia. There is evidence that suggests that the earliest wine production took place in Georgia and Iran around 6000 to 5000 B.C. The science of wine and winemaking is known as oenology. A winemaker may also be called a vintner. The growing of grapes is viticulture and there are many varieties of grapes.

<i>Brettanomyces</i> Genus of fungi

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 teleomorph or spore forming form of the yeast, but is considered deprecated under the one fungus, one name change. The cellular morphology of the yeast can vary from ovoid to long "sausage" shaped cells. The yeast is acidogenic, and when grown on glucose rich media under aerobic conditions, produces large amounts of acetic acid. Brettanomyces is important to both the brewing and wine industries due to the sensory compounds it produces.

<span class="mw-page-title-main">Malolactic fermentation</span> Process in winemaking

Malolactic conversion is a process in winemaking in which tart-tasting malic acid, naturally present in grape must, is converted to softer-tasting lactic acid. Malolactic fermentation is most often performed as a secondary fermentation shortly after the end of the primary fermentation, but can sometimes run concurrently with it. The process is standard for most red wine production and common for some white grape varieties such as Chardonnay, where it can impart a "buttery" flavor from diacetyl, a byproduct of the reaction.

<span class="mw-page-title-main">Kilju</span> Finnish home made alcoholic beverage

Kilju is the Finnish word for home made alcoholic beverage typically made of sugar, yeast, and water. The ABV is around 15–17%, and since it does not contain a sweet reserve it is completely dry. Crude fermented water may be distilled to moonshine. Kilju for consumption is clarified to avoid wine fault. It is a flax-colored alcoholic beverage with no discernible taste other than that of ethanol. It can be used as an ethanol base for drink mixers.

A wine fault is a sensory-associated (organoleptic) characteristic of a wine that is unpleasant, and may include elements of taste, smell, or appearance, elements that may arise from a "chemical or a microbial origin", where particular sensory experiences might arise from more than one wine fault. Wine faults may result from poor winemaking practices or storage conditions that lead to wine spoilage.

<span class="mw-page-title-main">Carbonate ester</span> Chemical group (R–O–C(=O)–O–R)

In organic chemistry, a carbonate ester is an ester of carbonic acid. This functional group consists of a carbonyl group flanked by two alkoxy groups. The general structure of these carbonates is R−O−C(=O)−O−R' and they are related to esters, ethers and also to the inorganic carbonates.

<i>Zygosaccharomyces bailii</i> Species of fungus

Zygosaccharomyces bailii is a species in the genus Zygosaccharomyces. It was initially described as Saccharomyces bailii by Lindner in 1895, but in 1983 it was reclassified as Zygosaccharomyces bailii in the work by Barnett et al.

<span class="mw-page-title-main">Dimethyl carbonate</span> Chemical compound

Dimethyl carbonate (DMC) is an organic compound with the formula OC(OCH3)2. It is a colourless, flammable liquid. It is classified as a carbonate ester. This compound has found use as a methylating agent and as a co-solvent in lithium-ion batteries. Notably, dimethyl carbonate is a weak methylating agent, and is not considered as a carcinogen. Instead, dimethyl carbonate is often considered to be a green reagent, and it is exempt from the restrictions placed on most volatile organic compounds (VOCs) in the United States.

<span class="mw-page-title-main">Potassium bisulfite</span> Chemical compound

Potassium bisulfite (or potassium hydrogen sulfite) is a chemical mixture with the approximately correctly mentioned formula chemical formula KHSO3. Potassium bisulfite in fact is not a real compound, but a mixture of salts that dissolve in water to give solutions composed of potassium ions and bisulfite ions. It is a white solid with an odor of sulfur dioxide. Attempts to crystallize potassium bisulfite yield potassium metabisulfite, K2S2O5.

<span class="mw-page-title-main">Fermentation in winemaking</span> Wine making process

The process of fermentation in winemaking turns grape juice into an alcoholic beverage. During fermentation, yeasts transform sugars present in the juice into ethanol and carbon dioxide. In winemaking, the temperature and speed of fermentation are important considerations as well as the levels of oxygen present in the must at the start of the fermentation. The risk of stuck fermentation and the development of several wine faults can also occur during this stage, which can last anywhere from 5 to 14 days for primary fermentation and potentially another 5 to 10 days for a secondary fermentation. Fermentation may be done in stainless steel tanks, which is common with many white wines like Riesling, in an open wooden vat, inside a wine barrel and inside the wine bottle itself as in the production of many sparkling wines.

<span class="mw-page-title-main">Cider</span> Fermented alcoholic beverage from apple juice

Cider is an alcoholic beverage made from the fermented juice of apples. Cider is widely available in the United Kingdom and Ireland. The UK has the world's highest per capita consumption, as well as the largest cider-producing companies. Ciders from the South West of England are generally higher in alcoholic content. Cider is also popular in many Commonwealth countries, such as India, South Africa, Canada, Australia, New Zealand, and New England. As well as the UK and its former colonies, cider is popular in Portugal, France, Friuli, and northern Spain. Germany also has its own types of cider with Rhineland-Palatinate and Hesse producing a particularly tart version known as Apfelwein. In the U.S. and Canada, varieties of alcoholic cider are often called hard cider to distinguish it from non-alcoholic apple cider or "sweet cider", also made from apples. In Canada, cider cannot contain less than 2.5% or over 13% absolute alcohol by volume.

This glossary of winemaking terms lists some of terms and definitions involved in making wine, fruit wine, and mead.

<span class="mw-page-title-main">Food spoilage</span> Often due to bacteria and fungi

Food spoilage is the process where a food product becomes unsuitable to ingest by the consumer. The cause of such a process is due to many outside factors as a side-effect of the type of product it is, as well as how the product is packaged and stored. Due to food spoilage, one-third of the world's food produced for the consumption of humans is lost every year. Bacteria and various fungi are the cause of spoilage and can create serious consequences for the consumers, but there are preventive measures that can be taken.

<span class="mw-page-title-main">Wine preservatives</span> Food preservation

Wine preservatives are used to preserve the quality and shelf life of bottled wine without affecting its taste. Specifically, they are used to prevent oxidation and bacterial spoilage by inhibiting microbial activity.

The topic of sulfite food and beverage additives covers the application of sulfites in food chemistry. "Sulfite" is jargon that encompasses a variety of materials that are commonly used as preservatives or food additive in the production of diverse foods and beverages. Although sulfite salts are relatively nontoxic, their use has led to controversy, resulting in extensive regulations. Sulfites are a source of sulfur dioxide (SO2), a bactericide.

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. ISBN   9783527306732.
  2. [ dead link ]
  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". Archived from the original on 2019-04-18. Retrieved 2010-12-15.