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dicarbonic acid, dimethyl ester
Notes:
Yeast inhibitor and preservative for alcoholic beverages esp. low alcohol wines
Dimethyl dicarbonate or DMDC is a colourless liquid with a sharp odour. Its primary use is as a beverage preservative and or processing aid or sterilant (INS No. 242), and acts by inhibiting the enzymes acetate kinase and L-glutamic acid decarboxylase. 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. Once it has been added to beverages, the efficacy of the chemical is provided by the following reactions:
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| CAS Number: | 4525-33-1 |  3D/inchi
|
| ECHA EINECS - REACH Pre-Reg: | 224-859-8 | |
| FDA UNII: | 1AY9229ZMG | |
| Nikkaji Web: | J205.896K | |
| Beilstein Number: | 0956715 | |
| MDL: | MFCD00008419 | |
| XlogP3-AA: | 0.70 (est) | |
| Molecular Weight: | 134.08782000 | |
| Formula: | C4 H6 O5 | |
| NMR Predictor: | Predict (works with chrome or firefox) | |
Category: antimicrobial agents
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
| Google Scholar: | Search |
| Google Books: | Search |
| Google Scholar: with word "volatile" | Search |
| Google Scholar: with word "flavor" | Search |
| Google Scholar: with word "odor" | Search |
| Perfumer and Flavorist: | Search |
| Google Patents: | Search |
| US Patents: | Search |
| EU Patents: | Search |
| Pubchem Patents: | Search |
| PubMed: | Search |
| NCBI: | Search |
| FDA/DG SANTE Petitions, Reviews, Notices: | |
| EU SANCO | Dimethyl dicarbonate View - review |
| FCN 35 | Dimethyl dicarbonate View - notice |
| FCN 483 | Dimethyl dicarbonate View - notice |
| JECFA Food Additive: | Dimethyl Dicarbonate |
| GSFA Codex: | Dimethyl dicarbonate (242) |
| DG SANTE Food Additives: | dimethyl dicarbonate |
| FDA Mainterm (SATF): | 4525-33-1 ; DIMETHYL DICARBONATE |
| FDA Regulation: | |
| FDA PART 172 -- FOOD ADDITIVES PERMITTED FOR DIRECT ADDITION TO FOOD FOR HUMAN CONSUMPTION Subpart B--Food Preservatives Sec. 172.133 Dimethyl dicarbonate. | |
Physical Properties:
| Appearance: | colorless clear liquid (est) |
| Assay: | 99.80 to 100.00 % |
| Food Chemicals Codex Listed: | No |
| Specific Gravity: | 1.25000 @ 25.00 °C. |
| Boiling Point: | 45.00 to 46.00 °C. @ 5.00 mm Hg |
| Vapor Pressure: | 1.399000 mmHg @ 25.00 °C. (est) |
| Flash Point: | 176.00 °F. TCC ( 80.00 °C. ) |
| logP (o/w): | 0.082 (est) |
| Soluble in: | |
| water, dec. | |
| toluene | |
| water, 4.771e+005 mg/L @ 25 °C (est) | |
Organoleptic Properties:
| Odor and/or flavor descriptions from others (if found). | |
Cosmetic Information:
| None found |
Suppliers:
| BOC Sciences |
| For experimental / research use only. |
| dimethyl dicarbonate 95% |
| EMD Millipore |
| For experimental / research use only. |
| Dimethyl Pyrocarbonate |
| Santa Cruz Biotechnology |
| For experimental / research use only. |
| Dimethyl dicarbonate |
| Sigma-Aldrich: Sigma |
| For experimental / research use only. |
| Dimethyl Pyrocarbonate for histidine methylation |
Safety Information:
| Preferred SDS: View | |
| Hazards identification | |
| Classification of the substance or mixture | |
| GHS Classification in accordance with 29 CFR 1910 (OSHA HCS) | |
| None found. | |
| GHS Label elements, including precautionary statements | |
| Pictogram | |
| Hazard statement(s) | |
| None found. | |
| Precautionary statement(s) | |
| None found. | |
| Oral/Parenteral Toxicity: | |
|
oral-rat LD50 260 mg/kg Weisheng Dulixue Zazhi. Journal of Health Toxicology. Vol. 6, Pg. 104, 1992. oral-mouse LD50 589 mg/kg Weisheng Dulixue Zazhi. Journal of Health Toxicology. Vol. 6, Pg. 104, 1992. | |
| Dermal Toxicity: | |
| Not determined | |
| Inhalation Toxicity: | |
|
inhalation-rat LC50 711 mg/m3/4H BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: TREMOR LUNGS, THORAX, OR RESPIRATION: DYSPNEA National Technical Information Service. Vol. OTS0545284 | |
Safety in Use Information:
| Category: | antimicrobial agents | ||
| Recommendation for dimethyl pyrocarbonate usage levels up to: | |||
| not for fragrance use. | |||
| Recommendation for dimethyl pyrocarbonate flavor usage levels up to: | |||
| not for flavor use. | |||
Safety References:
| European Food Safety Authority (EFSA) reference(s): | |
| Scientific opinion on the re-evaluation of dimethyl dicarbonate (DMDC, E 242) as a food additive View page or View pdf | |
| EPI System: | View |
| Cancer Citations: | Search |
| Toxicology Citations: | Search |
| EPA Substance Registry Services (TSCA): | 4525-33-1 |
| EPA ACToR: | Toxicology Data |
| EPA Substance Registry Services (SRS): | Registry |
| Laboratory Chemical Safety Summary : | 3086 |
| National Institute of Allergy and Infectious Diseases: | Data |
| WISER: | UN 2927 |
| WGK Germany: | 3 |
| methoxycarbonyl methyl carbonate | |
| Chemidplus: | 0004525331 |
| RTECS: | HT0362500 for cas# 4525-33-1 |
References:
| methoxycarbonyl methyl carbonate | |
| NIST Chemistry WebBook: | Search Inchi |
| Canada Domestic Sub. List: | 4525-33-1 |
| Pubchem (cid): | 3086 |
| Pubchem (sid): | 135020470 |
Other Information:
| (IUPAC): | Atomic Weights of the Elements 2011 (pdf) |
| Videos: | The Periodic Table of Videos |
| tgsc: | Atomic Weights use for this web site |
| (IUPAC): | Periodic Table of the Elements |
| FDA Substances Added to Food (formerly EAFUS): | View |
| HMDB (The Human Metabolome Database): | HMDB32872 |
| FooDB: | FDB010852 |
| Export Tariff Code: | 2920.90.5000 |
| FDA Listing of Food Additive Status: | View |
| ChemSpider: | View |
| Wikipedia: | View |
Potential Blenders and core components note
| None Found | ||
Potential Uses:
| None Found |
Occurrence (nature, food, other): note
| not found in nature |
Synonyms:
| carbonic acid, methoxycarbonyl methyl ester | |
| dicarbonic acid dimethyl ester | |
| dicarbonic acid, dimethyl ester | |
| dimethyl dicarbonate | |
| dimethyl oxydiformate | |
| dimethyldicarbonate | |
| DMPC | |
| formic acid, oxydi-, dimethyl ester | |
| methoxycarbonyl methyl carbonate | |
| pyrocarbonic acid dimethyl ester | |
| velcorin |