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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:52:23 UTC
Update Date2019-07-23 06:12:00 UTC
HMDB IDHMDB0032872
Secondary Accession Numbers
  • HMDB32872
Metabolite Identification
Common NameVelcorin
DescriptionYeast inhibitor and preservative for alcoholic beverages especially 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:.
Structure
Data?1563862320
Synonyms
ValueSource
Dicarbonic acid, c,c'-dimethyl esterHMDB
Dicarbonic acid, dimethyl esterHMDB
Dimethyl dicarbonateHMDB
Dimethyl oxydiformateHMDB
Dimethyl pyrocarbonateHMDB
DMPCHMDB
Formic acid, oxydi-, dimethyl esterHMDB
Formic acid, oxydi-, dimethyl ester (7ci,8ci)HMDB
Methyl pyrocarbonateHMDB
Pyrocarbonic acid dimethyl esterHMDB
Dimethyl dicarbonic acidGenerator
VelcorinMeSH
Chemical FormulaC4H6O5
Average Molecular Weight134.0874
Monoisotopic Molecular Weight134.021523302
IUPAC Namedimethyl dicarbonate
Traditional Namedimethyl dicarbonate
CAS Registry Number4525-33-1
SMILES
COC(=O)OC(=O)OC
InChI Identifier
InChI=1S/C4H6O5/c1-7-3(5)9-4(6)8-2/h1-2H3
InChI KeyGZDFHIJNHHMENY-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as organic carbonic acids and derivatives. Organic carbonic acids and derivatives are compounds comprising the organic carbonic acid or a derivative thereof.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassOrganic carbonic acids and derivatives
Sub ClassNot Available
Direct ParentOrganic carbonic acids and derivatives
Alternative Parents
Substituents
  • Carbonic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Source:

Biological location:

Role

Biological role:

Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point15 - 17 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility56.9 g/LALOGPS
logP0.05ALOGPS
logP0.93ChemAxon
logS-0.37ALOGPS
pKa (Strongest Basic)-5.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area61.83 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity25.33 m³·mol⁻¹ChemAxon
Polarizability11.41 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a59-9400000000-975623cc39a10d342c84Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0900000000-08abbf1269b9776cd507Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0900000000-cfb45e5c8d5ff7f9ba5eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-9300000000-93e530f54a98fd63c7ebSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0900000000-13d31e67944017e01f3eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0900000000-ebddd38c03b6410f52afSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ff0-4900000000-a4080f0ea0a4179e478aSpectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB010852
KNApSAcK IDNot Available
Chemspider ID2976
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkDimethyl dicarbonate
METLIN IDNot Available
PubChem Compound3086
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .