| Revision as of 17:31, 23 August 2011 editCheMoBot (talk | contribs)Bots141,565 edits Updating {{chembox}} (no changed fields - added verified revid - updated 'DrugBank_Ref', 'UNII_Ref', 'ChEMBL_Ref', 'ChEBI_Ref', 'KEGG_Ref', 'ChEBI_Ref') per Chem/Drugbox validation (report [[Wiki← Previous edit |
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{{chembox |
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{{chembox |
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| verifiedrevid = 446301690 |
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| verifiedrevid = 446348798 |
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| Name = Dimethyl dicarbonate |
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| ImageFile = Dimethyl-dicarbonate-2D-skeletal.png |
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| Name = Dimethyl dicarbonate |
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| ImageFile = Dimethyl-dicarbonate-2D-skeletal.png |
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| ImageName = Skeletal formula of dimethyl dicarbonate |
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| ImageName = Skeletal formula of dimethyl dicarbonate |
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| ImageFile1 = Dimethyl-dicarbonate-3D-balls.png |
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| ImageFile1 = Dimethyl-dicarbonate-3D-balls.png |
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| PIN = Dimethyl dicarbonate |
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| IUPACName = methoxycarbonyl methyl carbonate |
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| OtherNames = DMDC<br />dicarbonic acid<br />dimethyl ester<br />dimethyl pyrocarbonate<br />Velcorin |
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| OtherNames = DMDC; Dicarbonic acid dimethyl ester; Dimethyl pyrocarbonate; Velcorin |
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| Section1 = {{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| CASNo_Ref = {{cascite|correct|??}} |
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| SMILES = O=C(OC(=O)OC)OC |
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| CASNo = 4525-33-1 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChEBI = 173546 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 2976 |
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| ChemSpiderID = 2976 |
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| EC_number = 224-859-8 |
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| PubChem = 3086 |
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| PubChem = 3086 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = 1AY9229ZMG |
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| RTECS = |
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| InChI = 1/C4H6O5/c1-7-3(5)9-4(6)8-2/h1-2H3 |
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| InChI = 1/C4H6O5/c1-7-3(5)9-4(6)8-2/h1-2H3 |
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| InChIKey = GZDFHIJNHHMENY-UHFFFAOYAQ |
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| InChIKey = GZDFHIJNHHMENY-UHFFFAOYAQ |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = GZDFHIJNHHMENY-UHFFFAOYSA-N |
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| StdInChIKey = GZDFHIJNHHMENY-UHFFFAOYSA-N |
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| SMILES = O=C(OC(=O)OC)OC |
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| CASNo = 4525-33-1 |
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| RTECS = |
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| Section2 = {{Chembox Properties |
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|Section2={{Chembox Properties |
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| C = 4 |
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| Formula = C<sub>4</sub>H<sub>6</sub>O<sub>5</sub> |
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| MolarMass = 134.09 g/mol |
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| H = 6 |
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| O = 5 |
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| Appearance = Colourless liquid |
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| Density = 1.25 g/ml (liquid) |
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| Appearance = Colorless liquid |
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| Density = 1.25 g/mL |
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| SolubilityOther = |
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| Solvent = |
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| Solvent = |
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| MeltingPtC = 16 to 18 |
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| MeltingPt = 16–18 °C |
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| BoilingPt = 172 °C |
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| BoilingPtC = 172 |
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| Viscosity = 2.1 ] (20 °C) |
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| Viscosity = 2.1 ] (20 °C) |
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| SolubleOther = |
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| Section7 = {{Chembox Hazards |
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|Section7={{Chembox Hazards |
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| MainHazards = Toxic |
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| EUClass = |
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| MainHazards = Toxic |
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| GHSPictograms = {{GHS02}}{{GHS05}}{{GHS06}}{{GHS07}} |
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| RPhrases = 22-23-34 |
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| GHSSignalWord = Danger |
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| SPhrases = {{S7/9}}, {{S26}}, {{S36/37/39}}, {{S45}} |
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| HPhrases = {{H-phrases|226|302|312|314|330}} |
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| SPhrases = {{S7/9}}, {{S26}}, {{S36/37/39}}, {{S45}} |
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| PPhrases = {{P-phrases|210|233|240|241|242|243|260|264|270|271|280|284|301+312|301+330+331|302+352|303+361+353|304+340|305+351+338|310|312|320|321|322|330|363|370+378|403+233|403+235|405|501}} |
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}} |
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|Section8={{Chembox Related |
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| OtherCompounds = ]<BR>] |
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'''Dimethyl dicarbonate''' or '''DMDC''' is a colourless liquid with a sharp odour. Its primary use is as a ] ] and or processing aid or ] (] 242), and acts by ] the ]s ] and ].<ref name="Chembank1924"></ref> It has also been proposed that methoxycarbonylation of the ] part of the enzymes ] and ] by DMDC inhibits these essential enzymes also.<ref name="findarticles01"></ref> Once it has been added to beverages, the efficacy of the chemical is provided by the following reactions: |
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'''Dimethyl dicarbonate''' ('''DMDC''') is a colorless liquid with a pungent odor at high concentration at ]. It is primarily used as a ] ], processing aid, or ] (] 242) being highly active against typical beverage spoiling microorganisms like yeast, bacteria, or mould.<ref>{{Ullmann |doi=10.1002/14356007.a16_563.pub2|title=Biocides |year=2013 |last1=Uhr |first1=Hermann |last2=Mielke |first2=Burkhard |last3=Exner |first3=Otto |last4=Payne |first4=Ken R. |last5=Hill |first5=Edward |pages=1–26 |isbn=9783527306732 }}</ref> |
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*DMDC + H<sub>2</sub>O → 2CH<sub>3</sub>OH + 2CO<sub>2</sub> |
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== Usage == |
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*DMDC + EtOH → Ethyl methyl carbonate |
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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. |
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*DMDC + NH<sub>3</sub> → Methyl carbamate |
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*DMDC + ] → Derived carboxymethyl |
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It acts by ] ] involved in the microbial metabolism, e.g. ] and ].<ref name="Chembank1924">{{dead link|date=October 2011}}</ref> It has also been proposed that DMDC inhibits the enzymes ] and ] by causing the methoxycarbonylation of their ] components.<ref name="findarticles01"> {{Webarchive|url=https://web.archive.org/web/20150924053210/http://www.findarticles.com/p/articles/mi_m3488/is_n10_v71/ai_8963440 |date=2015-09-24 }}, Wines & Vines, Oct 1990</ref> |
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DMDC is sometimes used as a preservative in ] as a replacement to ], inactivating wine spoilage yeasts such as ]. In the U.S. the ] approved its use in wines in 1988, with the maximum permitted level being set at 200 mg/L, and only if there were fewer than 500 yeast cells/mL at time of dosage. Usage has also been approved in ] (since 1978) and ]. The application of DMDC is particularly useful when wine needs to be sterilised but cannot be sterile filtered, ], or sulfured. |
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In ], it is often used to replace ], as it inactivates ] such as '']''. Once it has been added to beverages, the efficacy of the chemical is provided by the following reactions: |
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DMDC is used to stabilise non alcoholic beverages such as carbonated or non carbonated juice beverages, isotonic sports beverages, iced teas and flavoured waters. |
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:DMDC + water → methanol + carbon dioxide |
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:DMDC + ethanol → ethyl methyl carbonate |
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:DMDC + ammonia → methyl carbamate |
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:DMDC + ] → derived carboxymethyl |
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The application of DMDC is particularly useful when wine needs to be sterilized but cannot be sterile filtered, ], 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® |
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DMDC is added before the filling of the beverage. It then breaks down into small amounts of ] and ], which are both natural constituents of fruit and vegetable juices. |
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DMDC is added before the filling of the beverage. It then breaks down into small amounts of ] and ], which are both natural constituents of fruit and vegetable juices. |
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The EU ], the ] in the United States and the ] of the WHO have confirmed the safe use in beverages. The ] 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.<ref>US Food and Drug Administration: {{cite web|url=https://www.fda.gov/Food/FoodIngredientsPackaging/FoodAdditives/FoodAdditiveListings/ucm091048.htm |title=Listing of Food Additives Status Part I |website=] |accessdate=2011-10-27 |url-status=dead |archiveurl=https://web.archive.org/web/20130314104055/https://www.fda.gov/Food/FoodIngredientsPackaging/FoodAdditives/FoodAdditiveListings/ucm091048.htm |archivedate=2013-03-14 }}</ref> It is also approved in the EU, where it is listed under ] E242,<ref>UK Food Standards Agency: {{cite web |url=http://www.food.gov.uk/safereating/chemsafe/additivesbranch/enumberlist |title=Current EU approved additives and their E Numbers |accessdate=2011-10-27}}</ref> as well as Australia and New Zealand.<ref>Food Standards Australia and New Zealand, Application A1015 - Classification of Dimethyl Dicarbonate - Approval Report -15 December 2010{{cite web |url=http://www.foodstandards.gov.au/code/applications/pages/applicationa1025clas4387.aspx |title=Application A1025 - Classification of Dimethyl Dicarbonate |accessdate=2010-12-15 |archive-date=2019-04-18 |archive-url=https://web.archive.org/web/20190418024916/http://www.foodstandards.gov.au/code/applications/Pages/applicationa1025clas4387.aspx |url-status=dead }}</ref> |
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The EU Scientific Committee on food, the ] in the United States and the JECFA of the WHO have confirmed the safe use in beverages. |
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==See also== |
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==References== |
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==External links== |
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==External links== |
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* {{Webarchive|url=https://web.archive.org/web/20150924053210/http://www.findarticles.com/p/articles/mi_m3488/is_n10_v71/ai_8963440 |date=2015-09-24 }} |
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{{DEFAULTSORT:Dimethyl Dicarbonate}} |
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{{DEFAULTSORT:Dimethyl Dicarbonate}} |
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