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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:52:23 UTC

Update Date

2023-02-21 17:22:42 UTC

HMDB ID

HMDB0032872

Secondary Accession Numbers

HMDB32872

Metabolite Identification

Common Name

Velcorin

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:.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

View in JSmol View NMR Assignments View Stereo Labels

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 Weight

134.0874

Monoisotopic Molecular Weight

134.021523302

IUPAC Name

dimethyl dicarbonate

Traditional Name

dimethyl dicarbonate

CAS Registry Number

4525-33-1

SMILES

COC(=O)OC(=O)OC

InChI Identifier

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

InChI 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

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0032872)
Cytoplasm (HMDB: HMDB0032872)

Source

Exogenous

Food

Food (HMDB: HMDB0032872)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0032872)

Physical Properties

State

Liquid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	15 - 17 °C	Not Available
Boiling Point	45.00 to 46.00 °C. @ 5.00 mm Hg	The Good Scents Company Information System
Water Solubility	0	The Good Scents Company Information System
LogP	0.082 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular 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	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	129.234	31661259
DarkChem	[M-H]-	124.45	31661259
DeepCCS	[M+H]+	117.316	30932474
DeepCCS	[M-H]-	114.159	30932474
DeepCCS	[M-2H]-	150.679	30932474
DeepCCS	[M+Na]+	125.874	30932474
AllCCS	[M+H]+	132.5	32859911
AllCCS	[M+H-H2O]+	128.6	32859911
AllCCS	[M+NH4]+	136.2	32859911
AllCCS	[M+Na]+	137.3	32859911
AllCCS	[M-H]-	125.8	32859911
AllCCS	[M+Na-2H]-	128.7	32859911
AllCCS	[M+HCOO]-	131.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Velcorin	COC(=O)OC(=O)OC	1478.0	Standard polar	33892256
Velcorin	COC(=O)OC(=O)OC	781.7	Standard non polar	33892256
Velcorin	COC(=O)OC(=O)OC	889.4	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Velcorin GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a59-9400000000-975623cc39a10d342c84	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Velcorin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Velcorin 10V, Positive-QTOF	splash10-000i-0900000000-08abbf1269b9776cd507	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Velcorin 20V, Positive-QTOF	splash10-000i-0900000000-cfb45e5c8d5ff7f9ba5e	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Velcorin 40V, Positive-QTOF	splash10-001i-9300000000-93e530f54a98fd63c7eb	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Velcorin 10V, Negative-QTOF	splash10-001i-0900000000-13d31e67944017e01f3e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Velcorin 20V, Negative-QTOF	splash10-001i-0900000000-ebddd38c03b6410f52af	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Velcorin 40V, Negative-QTOF	splash10-0ff0-4900000000-a4080f0ea0a4179e478a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Velcorin 10V, Positive-QTOF	splash10-052r-5900000000-a2b8ca8b01e3226a873f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Velcorin 20V, Positive-QTOF	splash10-0a4i-9100000000-eca7ef8fad6614a132f5	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Velcorin 40V, Positive-QTOF	splash10-0a4i-9000000000-fbfa86667cc6304351c8	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Velcorin 10V, Negative-QTOF	splash10-004i-9000000000-fec481e8e940c73f582d	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Velcorin 20V, Negative-QTOF	splash10-004i-9000000000-fec481e8e940c73f582d	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Velcorin 40V, Negative-QTOF	splash10-001i-9000000000-bc9b885c0afa3d6b95b1	2021-09-23	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB010852

KNApSAcK ID

Not Available

Chemspider ID

2976

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Dimethyl dicarbonate

METLIN ID

Not Available

PubChem Compound

3086

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1239601

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Velcorin (HMDB0032872)

MOL for HMDB0032872 (Velcorin)

3D MOL for HMDB0032872 (Velcorin)

3D SDF for HMDB0032872 (Velcorin)

3D-SDF for HMDB0032872 (Velcorin)

PDB for HMDB0032872 (Velcorin)

3D PDB for HMDB0032872 (Velcorin)

SMILES for HMDB0032872 (Velcorin)

INCHI for HMDB0032872 (Velcorin)

Structure for HMDB0032872 (Velcorin)

3D Structure for HMDB0032872 (Velcorin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra