E242 (Dimethyl dicarbonate) is a chemical compound, the dimethyl ester of dicarbonic acid.

It appears as a white powder that is highly reactive and easily hydrolysed in water or as a colourless liquid.

What it is used for and where

Food

Ingredient listed in the European food additives list as E242, preservative. It is used in the preservation of non-alcoholic and alcoholic beverages, especially in wines to prevent yeast spoilage, and is added before the bottling procedure. However, its efficacy in inactivating cellular enzymes is different for different yeast strains and species and is only active on microorganisms that are in a vegetative state (1).

When used in refrigerated environments, Dimethyl dicarbonate tends to solidify below 17° (2).

The critical toxic endpoint (liver) identified in the safety evaluation is carcinogenesis (3).

Dimethyl dicarbonate studies

• Molecular Formula     C₄H₆O₅      (CH₃OCO)₂O
• Molecular Weight      134.09
• CAS  4525-33-1
• UNII    1AY9229ZMG
• EC Number   224-859-8
• DSSTox ID  DTXSID2052108
• Nikkaji   J205.896K
• IUPAC  methoxycarbonyl methyl carbonate
• InChl=1S/C4H6O5/c1-7-3(5)9-4(6)8-2/h1-2H3
• InChl Key      GZDFHIJNHHMENY-UHFFFAOYSA-N
• SMILES  COC(=O)OC(=O)OC
• MDL number  MFCD00008419
• PubChem Substance ID    
• ChEBI  173546
• RTECS  HT0362500
• Metabolomics Workbench   45763  

Synonyms:

• dicarbonic acid dimethyl ester
• methoxycarbonyl methyl carbonate
• Dimethyl pyrocarbonate

References_____________________________________________________________________

(1) Shamsudin, R., Adzahan, N. M., Yee, Y. P., & Mansor, A. (2014). Effect of repetitive ultraviolet irradiation on the physico-chemical properties and microbial stability of pineapple juice. Innovative Food Science & Emerging Technologies, 23, 114-120.

(2) Lück, E., Jager, M., Lück, E., & Jager, M. (1997). Dicarbonic Acid Esters. Antimicrobial Food Additives: Characteristics· Uses· Effects, 168-173.

(3) Kramer NI, Hoffmans Y, Wu S, Thiel A, Thatcher N, Allen TEH, Levorato S, Traussnig H, Schulte S, Boobis A, Rietjens IMCM, Vinken M. Characterizing the coverage of critical effects relevant in the safety evaluation of food additives by AOPs. Arch Toxicol. 2019 Aug;93(8):2115-2125. doi: 10.1007/s00204-019-02501-x. 

Abstract. There is considerable interest in adverse outcome pathways (AOPs) as a means of organizing biological and toxicological information to assist in data interpretation and method development. While several chemical sectors have shown considerable progress in applying this approach, this has not been the case in the food sector. In the present study, safety evaluation reports of food additives listed in Annex II of Regulation (EC) No 1333/2008 of the European Union were screened to qualitatively and quantitatively characterize toxicity induced in laboratory animals. The resulting database was used to identify the critical adverse effects used for risk assessment and to investigate whether food additives share common AOPs. Analysis of the database revealed that often such scrutiny of AOPs was not possible or necessary. For 69% of the food additives, the report did not document any adverse effects in studies based on which the safety evaluation was performed. For the remaining 31% of the 326 investigated food additives, critical adverse effects and related points of departure for establishing health-based guidance values could be identified. These mainly involved effects on the liver, kidney, cardiovascular system, lymphatic system, central nervous system and reproductive system. AOPs are available for many of these apical endpoints, albeit to different degrees of maturity. For other adverse outcomes pertinent to food additives, including gastrointestinal irritation and corrosion, AOPs are lacking. Efforts should focus on developing AOPs for these particular endpoints.