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

2021-01-22 19:07:14 UTC

Update Date

2022-03-07 03:18:21 UTC

HMDB ID

HMDB0240744

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Dimethyl maleate

Description

Dimethyl maleate belongs to the class of organic compounds known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid. Dimethyl maleate is the methyl ester of maleic acid and the cis-isomer of dimethyl fumarate. Dimethyl maleate is a commonly used thiol-alkylating agent and enjoys widespread use in many organic synthesis (e.g. as a dienophile for diene syntheses). In the production of plastics, pigments, pharmaceuticals, and agricultural products, dimethyl maleate is used as an additive and an intermediate. In the production of paints, adhesives, and copolymers, dimethyl maleate is used as an intermediate.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
2-Butenedioic acid (2Z)-, dimethyl ester	ChEBI
2-Butenedioic acid (Z)-, dimethyl ester	ChEBI
Dimethyl cis-ethylenedicarboxylate	ChEBI
Maleic acid, dimethyl ester	ChEBI
Methyl maleate	ChEBI
2-Butenedioate (2Z)-, dimethyl ester	Generator
2-Butenedioate (Z)-, dimethyl ester	Generator
Dimethyl cis-ethylenedicarboxylic acid	Generator
Maleate, dimethyl ester	Generator
Methyl maleic acid	Generator
Dimethyl maleic acid	Generator
2-Butenedioic acid, dimethyl ester	HMDB
But-2-enedioic acid, dimethyl ester	HMDB
Dimethyl but-2-enedioate	HMDB

Chemical Formula

C₆H₈O₄

Average Molecular Weight

144.1253

Monoisotopic Molecular Weight

144.042258744

IUPAC Name

1,4-dimethyl (2Z)-but-2-enedioate

Traditional Name

dimethyl maleate

CAS Registry Number

624-48-6

SMILES

COC(=O)\C=C/C(=O)OC

InChI Identifier

InChI=1S/C6H8O4/c1-9-5(7)3-4-6(8)10-2/h3-4H,1-2H3/b4-3-

InChI Key

LDCRTTXIJACKKU-ARJAWSKDSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acid esters

Direct Parent

Fatty acid esters

Alternative Parents

Substituents

Fatty acid ester
Dicarboxylic acid or derivatives
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Methyl ester
Carboxylic acid ester
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

diester (CHEBI:35460 )
methyl ester (CHEBI:35460 )
maleate ester (CHEBI:35460 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0031257)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0031257)

Source

Exogenous

Exogenous (HMDB: HMDB0031257)

Food

Food (HMDB: HMDB0031257)

Endogenous

Endogenous (HMDB: HMDB0031257)

Animal

Animal (HMDB: HMDB0031257)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0031257)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0031257)

Lipid metabolism pathway (HMDB: HMDB0031257)

Cellular process

Cell signaling (HMDB: HMDB0031257)

Biochemical process

Lipid transport (HMDB: HMDB0031257)

Role

Biological role

Energy source (HMDB: HMDB0031257)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0031257)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	0.45	ALOGPS
logP	0.72	ChemAxon
logS	-1	ALOGPS
pKa (Strongest Basic)	-6.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	52.6 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	34.15 m³·mol⁻¹	ChemAxon
Polarizability	13.17 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]+	133.309	31661259
DarkChem	[M-H]-	127.841	31661259
DeepCCS	[M+H]+	118.559	30932474
DeepCCS	[M-H]-	114.725	30932474
DeepCCS	[M-2H]-	151.499	30932474
DeepCCS	[M+Na]+	127.115	30932474
AllCCS	[M+H]+	133.5	32859911
AllCCS	[M+H-H2O]+	129.4	32859911
AllCCS	[M+NH4]+	137.3	32859911
AllCCS	[M+Na]+	138.4	32859911
AllCCS	[M-H]-	129.7	32859911
AllCCS	[M+Na-2H]-	132.0	32859911
AllCCS	[M+HCOO]-	134.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Dimethyl maleate	COC(=O)\C=C/C(=O)OC	1760.5	Standard polar	33892256
Dimethyl maleate	COC(=O)\C=C/C(=O)OC	1032.9	Standard non polar	33892256
Dimethyl maleate	COC(=O)\C=C/C(=O)OC	1126.2	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Dimethyl maleate EI-B (Non-derivatized)	splash10-03di-7900000000-6c17ce0137a98251d821	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Dimethyl maleate EI-B (Non-derivatized)	splash10-03di-8900000000-cf4bc8e74198c9d1fbe2	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Dimethyl maleate EI-B (Non-derivatized)	splash10-03di-9800000000-9b43ca980ebe24e7dd08	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Dimethyl maleate EI-B (Non-derivatized)	splash10-03di-5900000000-155805a1d757b9c0e41b	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Dimethyl maleate EI-B (Non-derivatized)	splash10-03di-1900000000-7995ee86e999e5109520	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Dimethyl maleate EI-B (Non-derivatized)	splash10-03di-7900000000-6c17ce0137a98251d821	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Dimethyl maleate EI-B (Non-derivatized)	splash10-03di-8900000000-cf4bc8e74198c9d1fbe2	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Dimethyl maleate EI-B (Non-derivatized)	splash10-03di-9800000000-9b43ca980ebe24e7dd08	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Dimethyl maleate EI-B (Non-derivatized)	splash10-03di-5900000000-155805a1d757b9c0e41b	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Dimethyl maleate EI-B (Non-derivatized)	splash10-03di-1900000000-7995ee86e999e5109520	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dimethyl maleate GC-MS (Non-derivatized) - 70eV, Positive	splash10-01ql-9600000000-9b7e4e9fb1429b084be5	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dimethyl maleate 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 - Dimethyl maleate 10V, Positive-QTOF	splash10-01ot-0900000000-52a1c7b06f3e21edf137	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dimethyl maleate 20V, Positive-QTOF	splash10-01ot-3900000000-2c7c53ab39a3c1688bac	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dimethyl maleate 40V, Positive-QTOF	splash10-06sr-9200000000-509f89775c164df76c24	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dimethyl maleate 10V, Negative-QTOF	splash10-0006-0900000000-40c63012b9511f8490e3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dimethyl maleate 20V, Negative-QTOF	splash10-01ox-2900000000-c0fd047df97ddf890ee1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dimethyl maleate 40V, Negative-QTOF	splash10-001i-9200000000-89cb0515dab9e09d5146	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dimethyl maleate 10V, Positive-QTOF	splash10-01p9-9500000000-33bc0abdab46b5a42b1f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dimethyl maleate 20V, Positive-QTOF	splash10-0k9l-9000000000-12b87d2f6c05d6047916	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dimethyl maleate 40V, Positive-QTOF	splash10-0zfr-9000000000-cc19a5706e05ef5eb348	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dimethyl maleate 10V, Negative-QTOF	splash10-03di-1900000000-1d56ae91abb29a4fba91	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dimethyl maleate 20V, Negative-QTOF	splash10-0gx0-9300000000-13e505571c984fd1ebfb	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dimethyl maleate 40V, Negative-QTOF	splash10-066r-9000000000-494ce88adb3552f6a330	2021-09-22	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

Biological Properties

Cellular Locations

Not Available

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

FDB003290

KNApSAcK ID

Not Available

Chemspider ID

4436352

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Dimethyl_maleate

METLIN ID

Not Available

PubChem Compound

5271565

PDB ID

Not Available

ChEBI ID

35460

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1239471

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for Dimethyl maleate (HMDB0240744)

MOL for HMDB0240744 (Dimethyl maleate)

3D MOL for HMDB0240744 (Dimethyl maleate)

3D SDF for HMDB0240744 (Dimethyl maleate)

3D-SDF for HMDB0240744 (Dimethyl maleate)

PDB for HMDB0240744 (Dimethyl maleate)

3D PDB for HMDB0240744 (Dimethyl maleate)

SMILES for HMDB0240744 (Dimethyl maleate)

INCHI for HMDB0240744 (Dimethyl maleate)

Structure for HMDB0240744 (Dimethyl maleate)

3D Structure for HMDB0240744 (Dimethyl maleate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra