ContaminantDB: DIMETHYL DICARBONATE

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-05-19 02:01:49 UTC

Update Date

2016-11-09 01:09:32 UTC

Accession Number

CHEM005407

Identification

Common Name

DIMETHYL DICARBONATE

Class

Small Molecule

Description

Yeast 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:.

Contaminant Sources

EAFUS Chemicals
FooDB Chemicals
STOFF IDENT Compounds

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Dicarbonic acid, c,c'-dimethyl ester	HMDB
Dicarbonic acid, dimethyl ester	HMDB
Dimethyl dicarbonate	HMDB
Dimethyl oxydiformate	HMDB
Dimethyl pyrocarbonate	HMDB, MeSH
DMPC	HMDB
Formic acid, oxydi-, dimethyl ester	HMDB
Formic acid, oxydi-, dimethyl ester (7ci,8ci)	HMDB
Methyl pyrocarbonate	HMDB
Pyrocarbonic acid dimethyl ester	HMDB
Dimethyl dicarbonic acid	Generator
Velcorin	MeSH

Chemical Formula

C₄H₆O₅

Average Molecular Mass

134.087 g/mol

Monoisotopic Mass

134.022 g/mol

CAS Registry Number

4525-33-1

IUPAC Name

dimethyl dicarbonate

Traditional Name

dimethyl dicarbonate

SMILES

COC(=O)OC(=O)OC

InChI Identifier

InChI=1S/C4H6O5/c1-7-3(5)9-4(6)8-2/h1-2H3

InChI Key

GZDFHIJNHHMENY-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.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Organic carbonic acids and derivatives

Sub Class

Not Available

Direct Parent

Organic 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 Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	56.9 g/L	ALOGPS
logP	0.05	ALOGPS
logP	0.93	ChemAxon
logS	-0.37	ALOGPS
pKa (Strongest Basic)	-5.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	61.83 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	25.33 m³·mol⁻¹	ChemAxon
Polarizability	11.41 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a59-9400000000-975623cc39a10d342c84	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0900000000-08abbf1269b9776cd507	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-0900000000-cfb45e5c8d5ff7f9ba5e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001i-9300000000-93e530f54a98fd63c7eb	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0900000000-13d31e67944017e01f3e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-0900000000-ebddd38c03b6410f52af	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0ff0-4900000000-a4080f0ea0a4179e478a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-052r-5900000000-a2b8ca8b01e3226a873f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-9100000000-eca7ef8fad6614a132f5	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9000000000-fbfa86667cc6304351c8	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-9000000000-fec481e8e940c73f582d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9000000000-fec481e8e940c73f582d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-001i-9000000000-bc9b885c0afa3d6b95b1	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

Not Available

Uses/Sources

Not Available

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0032872

FooDB ID

FDB010852

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Dimethyl dicarbonate

Chemspider ID

2976

ChEBI ID

Not Available

PubChem Compound ID

3086

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

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.

DIMETHYL DICARBONATE (CHEM005407)

Structure for CHEM005407: DIMETHYL DICARBONATE