Jump To Section:

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 17:22:43 UTC

HMDB ID

HMDB0032873

Secondary Accession Numbers

HMDB32873

Metabolite Identification

Common Name

Diethyl dicarbonate

Description

Diethyl dicarbonate, also known as diethyl oxydiformate or pyrocarbonate d'ethyle, 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. Based on a literature review very few articles have been published on Diethyl dicarbonate.

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 diethyl ester	ChEBI
Diethyl oxydiformate	ChEBI
Diethyl pyrocarbonic acid	ChEBI
Ethyl pyrocarbonate	ChEBI
Oxydiformic acid diethyl ester	ChEBI
Pyrocarbonate d'ethyle	ChEBI
Pyrocarbonic acid diethyl ester	ChEBI
Pyrokohlensaeure diaethyl ester	ChEBI
Dicarbonate diethyl ester	Generator
Diethyl oxydiformic acid	Generator
Diethyl pyrocarbonate	Generator
Ethyl pyrocarbonic acid	Generator
Oxydiformate diethyl ester	Generator
Pyrocarbonic acid d'ethyle	Generator
Pyrocarbonate diethyl ester	Generator
Diethyl dicarbonic acid	Generator
Anhydride, ethoxyformic	MeSH
Dicarbonate, diethyl	MeSH
Diethylpyrocarbonate	MeSH
Ethoxyformic anhydride	MeSH
Oxydiformate, diethyl	MeSH
Pyrocarbonate, diethyl	MeSH
Baycovin	HMDB
DEPC	HMDB
Dicarbonic acid, c,c'-diethyl ester	HMDB
Dicarbonic acid, diethyl ester	HMDB
Diethyl ester OF pyrocarbonic acid	HMDB
Diethylester kyseliny diuhlicite	HMDB
Diethylpyrokarbonat	HMDB
DKD	HMDB
Ethoxyformic acid anhydride	HMDB
Formic acid, oxydi-, diethyl ester	HMDB
Piref	HMDB
Pyrocarbonic acid, diethyl ester	HMDB
Diethyl dicarbonate	MeSH

Chemical Formula

C₆H₁₀O₅

Average Molecular Weight

162.1406

Monoisotopic Molecular Weight

162.05282343

IUPAC Name

diethyl dicarbonate

Traditional Name

diethyl pyrocarbonate

CAS Registry Number

1609-47-8

SMILES

CCOC(=O)OC(=O)OCC

InChI Identifier

InChI=1S/C6H10O5/c1-3-9-5(7)11-6(8)10-4-2/h3-4H2,1-2H3

InChI Key

FFYPMLJYZAEMQB-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

acyclic carboxylic anhydride (CHEBI:59051 )
a small molecule (DIETHYLPYROCARBONATE )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0032873)
Cytoplasm (HMDB: HMDB0032873)

Source

Exogenous

Exogenous (HMDB: HMDB0032873)

Food

Food (HMDB: HMDB0032873)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0032873)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	< 25 °C	Not Available
Boiling Point	172.00 to 173.00 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	52250 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	1.101 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	12.4 g/L	ALOGPS
logP	0.98	ALOGPS
logP	1.64	ChemAxon
logS	-1.1	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	6	ChemAxon
Refractivity	34.83 m³·mol⁻¹	ChemAxon
Polarizability	15.59 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]+	135.956	31661259
DarkChem	[M-H]-	131.961	31661259
DeepCCS	[M+H]+	131.636	30932474
DeepCCS	[M-H]-	129.364	30932474
DeepCCS	[M-2H]-	165.825	30932474
DeepCCS	[M+Na]+	140.664	30932474
AllCCS	[M+H]+	136.7	32859911
AllCCS	[M+H-H2O]+	132.8	32859911
AllCCS	[M+NH4]+	140.3	32859911
AllCCS	[M+Na]+	141.3	32859911
AllCCS	[M-H]-	133.9	32859911
AllCCS	[M+Na-2H]-	135.9	32859911
AllCCS	[M+HCOO]-	138.1	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	6.6 minutes	32390414
Predicted by Siyang on May 30, 2022	14.7381 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.85 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2332.9 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	487.9 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	181.8 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	337.2 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	166.5 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	555.5 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	831.2 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	112.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1164.5 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	396.5 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1453.0 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	352.6 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	451.4 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	649.3 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	563.7 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	149.9 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Diethyl dicarbonate	CCOC(=O)OC(=O)OCC	1614.6	Standard polar	33892256
Diethyl dicarbonate	CCOC(=O)OC(=O)OCC	925.9	Standard non polar	33892256
Diethyl dicarbonate	CCOC(=O)OC(=O)OCC	993.0	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 - Diethyl dicarbonate GC-MS (Non-derivatized) - 70eV, Positive	splash10-004i-9100000000-fd82676bac939730c59d	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Diethyl dicarbonate 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 - Diethyl dicarbonate 10V, Positive-QTOF	splash10-03di-3900000000-8a13fdcc2f2883160d6f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diethyl dicarbonate 20V, Positive-QTOF	splash10-03dr-9800000000-ec09388ee3783fba54a8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diethyl dicarbonate 40V, Positive-QTOF	splash10-0002-9000000000-d694a2695857589eadbe	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diethyl dicarbonate 10V, Negative-QTOF	splash10-03di-4900000000-b9e388612a87a1877adf	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diethyl dicarbonate 20V, Negative-QTOF	splash10-01b9-9700000000-25a44a42ef27d577b0ef	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diethyl dicarbonate 40V, Negative-QTOF	splash10-000b-9100000000-932a15a6856f1679c011	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diethyl dicarbonate 10V, Positive-QTOF	splash10-02mu-8900000000-5f915080ed469701afce	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diethyl dicarbonate 20V, Positive-QTOF	splash10-059l-9300000000-ad7a1f5ef47de6404cfc	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diethyl dicarbonate 40V, Positive-QTOF	splash10-00dm-9000000000-7ba5bbb916c7704efbea	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diethyl dicarbonate 10V, Negative-QTOF	splash10-03dr-5900000000-ac11ce22d17697b3b7fb	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diethyl dicarbonate 20V, Negative-QTOF	splash10-007c-9000000000-bc9fd181a91cd4c3bf99	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diethyl dicarbonate 40V, Negative-QTOF	splash10-0005-9000000000-0290f494e8cc18ef577f	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
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, 100 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, 1000 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, 200 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, 300 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, 400 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, 500 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, 600 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, 700 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, 800 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
Predicted 1D NMR	¹H 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

FDB010853

KNApSAcK ID

Not Available

Chemspider ID

2943

KEGG Compound ID

C11592

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

3051

PDB ID

Not Available

ChEBI ID

59051

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1237761

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 Diethyl dicarbonate (HMDB0032873)

MOL for HMDB0032873 (Diethyl dicarbonate)

3D MOL for HMDB0032873 (Diethyl dicarbonate)

3D SDF for HMDB0032873 (Diethyl dicarbonate)

3D-SDF for HMDB0032873 (Diethyl dicarbonate)

PDB for HMDB0032873 (Diethyl dicarbonate)

3D PDB for HMDB0032873 (Diethyl dicarbonate)

SMILES for HMDB0032873 (Diethyl dicarbonate)

INCHI for HMDB0032873 (Diethyl dicarbonate)

Structure for HMDB0032873 (Diethyl dicarbonate)

3D Structure for HMDB0032873 (Diethyl dicarbonate)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra