Chemical Properties
liquid
Uses
Gentle esterifying agent. Preservative for wines, soft drinks, fruit juices.
Uses
Modification reagent for His and Tyr residues in proteins. Robust probe for structural disruptions in dsDNA, reacting with fully or partially unstacked bases.1
Definition
ChEBI: The diethyl ester of dicarbonic acid.
Production Methods
Diethyl dicarbonate is manufactured commercially through a carefully controlled ester forming process that brings together ethanol derived intermediates with carbonylating agents under anhydrous, catalytic conditions. In a typical industrial route, ethanol is first converted to ethyl chloroformate or another activated carbonate species, which then undergoes a carbonylation or transesterification reaction, often using phosgene substitutes or carbon monoxide-based chemistry, to form the diethyl dicarbonate molecule. These reactions take place in closed reactors where temperature, pressure, and moisture levels are tightly regulated to prevent decomposition and ensure high purity.
General Description
Diethyl pyrocarbonate (DEP) is a bactericidal agent and decomposes in water to CO2 and ethanol. DEP inhibits enzymes such as DNase and RNase without affecting nucleic acids. It is useful for the preparation of mRNA from tissues.
Biochem/physiol Actions
Inactivates RNase in solution at about 0.1% (v/v), thus protecting RNA against degradation.
Mechanism of action
Disrupts the function of enzymes and proteins - chemically modifies amino acid residues in proteins (histidine, lysine, cysteine & tyrosine)
Purification Methods
Dissolve the ester in Et2O, wash it with dilute HCl, H2O, dry over Na2SO4, filter, evaporate and distil the residue first in vacuo then at atmospheric pressure. It is soluble in alcohols, esters, ketones and hydrocarbon solvents. A 50% w/w solution is usually prepared for general use. Treat with great CAUTION as DEP irritates the eyes, mucous membranes and skin. [Boehm & Mehta Chem Ber 71 1797 1938, Thoma & Rinke Justus Liebigs Ann Chem 624 30 1959, Beilstein 3 IV 18.]
