2-Butenedioic acid (2Z)-, 1,4-dimethyl ester (CED0159006)

Record Information

Version

1.0

Creation Date

2016-05-19 04:08:47 UTC

Update Date

2026-04-17 18:02:27 UTC

Accession Number

CHEM013160

Identification

Common Name

2-Butenedioic acid (2Z)-, 1,4-dimethyl ester

Class

Small Molecule

Description

2-Butenedioic acid (2Z)-, 1,4-dimethyl ester is an organic compound with the chemical formula C6H8O4 and an average molecular weight of 144.13 g/mol. 2-Butenedioic acid (2Z)-, 1,4-dimethyl ester belongs to the fatty acid esters, a subclass of fatty acyls within the organic compounds. Industrially, this substance is utilized as a plasticizer. The compound is associated with nine recorded sources. Within the category of electrical and electronic equipment, it is found in antennas, magnets, power cables, emergency protective devices, and gas filled discharge tubes with solid cathode. In building and construction applications, it is linked to tents or canopies as well as stairs and ramps. Additionally, it has been identified in food contact materials used in food, food processing and cookware, as well as in drinking water and water supply. Recorded exposure routes for this compound include oral intake, inhalation, and touch.

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

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 Mass

144.125 g/mol

Monoisotopic Mass

144.042 g/mol

CAS Registry Number

624-48-6

IUPAC Name

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

Traditional Name

dimethyl maleate

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 )

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Organoleptic Effects

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	12.9 g/L	ALOGPS
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

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
GC-MS	GC-MS Spectrum	splash10-03di-7900000000-6c17ce0137a98251d821	Not Available	View Spectrum
GC-MS	GC-MS Spectrum	splash10-03di-8900000000-cf4bc8e74198c9d1fbe2	Not Available	View Spectrum
GC-MS	GC-MS Spectrum	splash10-03di-9800000000-9b43ca980ebe24e7dd08	Not Available	View Spectrum
GC-MS	GC-MS Spectrum	splash10-03di-5900000000-155805a1d757b9c0e41b	Not Available	View Spectrum
GC-MS	GC-MS Spectrum	splash10-03di-1900000000-7995ee86e999e5109520	Not Available	View Spectrum
GC-MS	GC-MS Spectrum	splash10-03di-7900000000-6c17ce0137a98251d821	Not Available	View Spectrum
GC-MS	GC-MS Spectrum	splash10-03di-8900000000-cf4bc8e74198c9d1fbe2	Not Available	View Spectrum
GC-MS	GC-MS Spectrum	splash10-03di-9800000000-9b43ca980ebe24e7dd08	Not Available	View Spectrum
GC-MS	GC-MS Spectrum	splash10-03di-5900000000-155805a1d757b9c0e41b	Not Available	View Spectrum
GC-MS	GC-MS Spectrum	splash10-03di-1900000000-7995ee86e999e5109520	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	splash10-01ql-9600000000-9b7e4e9fb1429b084be5	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-01ot-0900000000-52a1c7b06f3e21edf137	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-01ot-3900000000-2c7c53ab39a3c1688bac	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-06sr-9200000000-509f89775c164df76c24	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0006-0900000000-40c63012b9511f8490e3	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-01ox-2900000000-c0fd047df97ddf890ee1	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-001i-9200000000-89cb0515dab9e09d5146	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-01p9-9500000000-33bc0abdab46b5a42b1f	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0k9l-9000000000-12b87d2f6c05d6047916	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0zfr-9000000000-cc19a5706e05ef5eb348	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-03di-1900000000-1d56ae91abb29a4fba91	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0gx0-9300000000-13e505571c984fd1ebfb	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-066r-9000000000-494ce88adb3552f6a330	Not Available	View Spectrum
1D NMR	¹H NMR Spectrum (1D, D₂O, predicted)	Not Available	Not Available	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, D₂O, predicted)	Not Available	Not Available	View Spectrum

Toxicity Profile

Mechanism of Toxicity

Not Available

Carcinogenicity (IARC Classification)

Not Available

Minimum Risk Level

Not Available

Symptoms

Not Available

Treatment

Not Available

Toxicity Values

Toxicity Value	Unit	Value Range	Organism	Dose Descriptor	Route of Exposure	Predicted or Experimental	Reference
2638.0	Log mg/kg	[1500:4700]	Rat	LD50	oral	predicted	Not Available

Health Effects

Health Effect	Relationship	Direction	Reference

Exposure Sources

Source ID	Source	Sector	Reference
115	Drinking water	Drinking water & water supply	Not Available
490		Personal care & cosmetics	Not Available
494	Food contact materials	Food, food processing & cookware	Not Available
500	Stairs And Ramps	Building & Construction	Not Available
503	Tents Or Canopies	Building & Construction	Not Available
506	Antennas	Electrical & Electronic Equipment	Not Available
520	Emergency Protective Devices	Electrical & Electronic Equipment	Not Available
523	Gas Filled Discharge Tubes With Solid Cathode	Electrical & Electronic Equipment	Not Available
527	Magnets	Electrical & Electronic Equipment	Not Available
529	Power Cables	Electrical & Electronic Equipment	Not Available
633	Azo Dyes	Textiles, leather & furnishings	Not Available
640	Embroidering And Tufting	Textiles, leather & furnishings	Not Available
647	Multicolour Dyeing	Textiles, leather & furnishings	Not Available
653	Sewing	Textiles, leather & furnishings	Not Available
658	Touch Fasteners	Textiles, leather & furnishings	Not Available

Pathways

1 pathway

Dimethyl fumarate Drug Metabolism Action Pathway

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	Nuclear factor erythroid 2-related factor 2	Q16236	Humans	Predicted (SEA)	2.80257
Click to view 3D structure	Hydroxycarboxylic acid receptor 2	Q8TDS4	Humans	Predicted (SEA)	2.88042
Click to view 3D structure	Cytochrome P450 2C23	P24470	Rattus norvegicus	Predicted (SEA)	4.35956
Click to view 3D structure	Transcription factor EB	P19484	Humans	Predicted (SEA)	31.6068
Click to view 3D structure	Glutamine--fructose-6-phosphate aminotransferase [isomerizing] 1	Q06210	Humans	Predicted (SEA)	0.700643
Click to view 3D structure	Carbonic anhydrase 2	P00918	Humans	Predicted (SEA)	1128.74
Click to view 3D structure	Carbonic anhydrase 1	P00915	Humans	Predicted (SEA)	1328.73
Click to view 3D structure	Carbonic anhydrase 9	Q16790	Humans	Predicted (SEA)	1313.71
Click to view 3D structure	Carbonic anhydrase 12	O43570	Humans	Predicted (SEA)	1185.57
Click to view 3D structure	Carbonic anhydrase 14	Q9ULX7	Humans	Predicted (SEA)	794.685
Click to view 3D structure	Amine oxidase [flavin-containing] B	P27338	Humans	Predicted (SEA)	1626.19
Click to view 3D structure	Carbonic anhydrase 7	P43166	Humans	Predicted (SEA)	1076.34
Click to view 3D structure	Tissue factor	P13726	Humans	Predicted (SEA)	154.297
Click to view 3D structure	Polyunsaturated fatty acid 5-lipoxygenase	P09917	Humans	Predicted (SEA)	1041.0
Click to view 3D structure	Aldo-keto reductase family 1 member B1	P15121	Humans	Predicted (SEA)	489.672
Click to view 3D structure	Fructose-bisphosphate aldolase class 2	P0AB71	Escherichia coli (strain K12)	Predicted (SEA)	2.33548
Click to view 3D structure	Matrix metalloproteinase-9	P14780	Humans	Predicted (SEA)	2618.46
Click to view 3D structure	Protein deacetylase HDAC6	Q9UBN7	Humans	Predicted (SEA)	4487.31
Click to view 3D structure	Carbonic anhydrase 6	P23280	Humans	Predicted (SEA)	1196.31
Click to view 3D structure	Amyloid-beta precursor protein	P05067	Humans	Predicted (SEA)	1459.52
Click to view 3D structure	Broad substrate specificity ATP-binding cassette transporter ABCG2	Q9UNQ0	Humans	Predicted (SEA)	2059.81
Click to view 3D structure	72 kDa type IV collagenase	P08253	Humans	Predicted (SEA)	3632.13
Click to view 3D structure	Poly [ADP-ribose] polymerase 1	P09874	Humans	Predicted (SEA)	2097.8
Click to view 3D structure	11-beta-hydroxysteroid dehydrogenase 1	P16232	Rattus norvegicus	Predicted (SEA)	90.3051
Click to view 3D structure	Histone deacetylase 1	Q13547	Humans	Predicted (SEA)	4773.4