Dimethyl dicarbonate
General
Systematic name	methoxycarbonyl methyl carbonate
Other names	DMDC dicarbonic acid dimethyl ester dimethyl pyrocarbonate Velcorin®
Molecular formula	C4H6O5
SMILES	O=C(OC(=O)OC)OC
Molar mass	134.09 g/mol
Appearance	Colourless liquid
CAS number	[4525-33-1]
Properties
Density and phase	1.25 g/ml, liquid
Solubility in water	3.4 g/100 ml (20 °C)
Melting point	16-18°C
Boiling point	172°C
Viscosity	2.1 Pa.s at 20 °C
Hazards
MSDS	External MSDS
Main hazards	Toxic
R-phrases	22-23-34
S-phrases	S7/9, S26, S36/37/39, S45
Flash point	85°C
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references

Dimethyl dicarbonate or DMDC is a colourless liquid with a sharp odour. Its primary use is as a beverage preservative 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: IUPAC nomenclature is a system of naming chemical compounds and of describing the science of chemistry in general. ... A chemical formula (also called molecular formula) is a concise way of expressing information about the atoms that constitute a particular chemical compound. ... The simplified molecular input line entry specification or SMILES is a specification for unambiguously describing the structure of chemical molecules using short ASCII strings. ... Molar mass is the mass of one mole of a chemical element or chemical compound. ... CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences, mixtures and alloys. ... Density (symbol: ρ - Greek: rho) is a measure of mass per unit of volume. ... In the physical sciences, a phase is a set of states of a macroscopic physical system that have relatively uniform chemical composition and physical properties (i. ... A substance is soluble in a fluid if it dissolves in that fluid. ... Water has the chemical formula H2O, meaning that one molecule of water is composed of two hydrogen atoms and one oxygen atom. ... The melting point of a solid is the temperature at which it changes state from solid to liquid. ... The boiling point of a substance is the temperature at which it can change its state from a liquid to a gas throughout the bulk of the liquid. ... The pitch drop experiment at the University of Queensland. ... The pascal second (symbol Pa·s) is the SI unit of dynamic viscosity. ... A material safety data sheet or MSDS is a form containing data regarding the properties of a particular substance. ... Worker safety and health is the prevention and reduction of the number of occupational safety and health hazards at the places of employment, providing safe and healthful working conditions. ... R-phrases are defined in Annex III of European Union Directive 67/548/EEC: Nature of special risks attributed to dangerous substances and preparations. ... S-phrases are defined in Annex IV of European Union Directive 67/548/EEC: Safety advice concerning dangerous substances and preparations. ... The flash point of a fuel is the lowest temperature at which it can form an ignitable mix with air. ... In chemistry, the standard state of a material is its state at 1 bar (100 kilopascals) and 25 degrees Celsius (298. ... The word drink is primarily a verb, meaning to ingest liquids. ... A preservative is a natural or synthetic chemical that is added to products such as foods, pharmaceuticals, paints, biological samples, etc. ... Sterilization (or sterilisation) is the elimination of all transmissible agents (such as bacteria, prions and viruses) from a surface, a piece of equipment, food or biological culture medium. ... An inhibitor is a type of effector (biology) that decreases or prevents a chemical reaction. ... Ribbon diagram of the catalytically perfect enzyme TIM. An enzyme is a protein that catalyzes, or speeds up, a chemical reaction. ... Acetate, or ethanoate, is the anion of a salt or ester of acetic acid. ... In biochemistry, a kinase is a type of enzyme that transfers phosphate groups from high-energy donor molecules, such as ATP, to specific target molecules (substrates); the process is termed phosphorylation. An enzyme that removes phosphate groups from targets is known as a phosphatase. ... L-Glutamic acid decarboxylase (GAD) is an enzyme necessary for the synthesis of the inhibitory neurotransmitter GABA in GABAergic nerve endings. ... Histidine is one of the 20 most common natural amino acids, coded for in DNA. Nutritionally, in humans, histidine is considered an essential amino acid, but mostly only in children. ... Alcohol Dehydrogenase Alcohol dehydrogenases are a group of dehydrogenase enzymes that occur in many organisms and facilitate the conversion between alcohols and aldehydes or ketones. ...

• DMDC + H₂O → 2CH₃OH + 2CO₂
• DMDC + ROH → 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 1998, with the maximum permitted level being set at 200mg/L, and only if there was less than 500 yeast cells/mL at time of dosage. Usage has also been approved in Germany (since 1978) and New Zealand. The application of DMDC is particularly useful when wine needs to be sterilised but cannot be sterile filtered, pasteurized, or sulfured. In chemistry, an amino acid is any molecule that contains both amino and carboxylic acid functional groups. ... Wine is an alcoholic beverage produced by the fermentation of grapes and grape juice. ... Sulfur dioxide (or Sulphur dioxide) has the chemical formula SO2. ... [[|Diversity]] Binomial name Trinomial name Type Species Species [[Image: ]] Synonyms Brettanomyces is a single-celled fungus that is important in brewing and winemaking as it is resistant to alcohol so can grow even after fermentation starts. ... The Food and Drug Administration (FDA) of the United States is the government agency responsible for regulating food (human and animal), dietary supplements, drugs (human and animal), cosmetics, medical devices (human and animal), biologics, and blood products in the United States. ... Pasteurization (or pasteurisation) is the process of heating food for the purpose of killing harmful organisms such as bacteria, viruses, protozoa, molds, and yeasts. ...

DMDC has also been used to sterilise coffee, tea, cider, fruit wine, and mead. Coffee in beverage form. ... Tea leaves in a teacup. ... A pint of Strongbow cider. ... Fruit wines are wine-like beverages made from fruits other than grapes. ... Mead Wikibooks Cookbook has more about this subject: Mead Mead is a fermented alcoholic beverage made of honey, water, and yeast. ...

External links

• Dimethyl dicarbonate at EPA SRS
• Dimethyl dicarbonate technical data at Panreac
• Dimethyl dicarbonate technical data at FAO
• Dimethyl dicarbonate and microbiological stability