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CHEBI:68508 - diethyl maleate

ChEBI IDCHEBI:68508
ChEBI Namediethyl maleate
Stars
DefinitionA maleate ester resulting from the formal condensation of both carboxy groups of maleic acid with ethanol. A colourless liquid at room temperature (m.p. -10°C) with boiling point 220°C at 1 atm., it is commonly used as a dienophile for Diels-Alder-type cycloaddition reactions in organic synthesis.
Last Modified2 March 2015
SubmitterGareth Owen
DownloadsMolfile
FormulaC8H12O4
Net Charge0
Average Mass172.180
Monoisotopic Mass172.07356
SMILESCCOC(=O)/C=C\C(=O)OCC
InChIInChI=1S/C8H12O4/c1-3-11-7(9)5-6-8(10)12-4-2/h5-6H,3-4H2,1-2H3/b6-5-
InChIKeyIEPRKVQEAMIZSS-WAYWQWQTSA-N
Roles Classification
Biological Role:
glutathione depleting agent  A compound which causes a reduction in the levels of glutathione in cells.
ChEBI Ontology
Outgoing Relation(s)
diethyl maleate (CHEBI:68508) has functional parent ethanol (CHEBI:16236)
diethyl maleate (CHEBI:68508) has role glutathione depleting agent (CHEBI:68509)
diethyl maleate (CHEBI:68508) is a ethyl ester (CHEBI:23990)
diethyl maleate (CHEBI:68508) is a maleate ester (CHEBI:35486)
IUPAC Name 
diethyl (2Z)-but-2-enedioate
Synonyms  Source
2-butenedioic acid (2Z)-, dimethyl esterChemIDplus
maleic acid, diethyl esterNIST Chemistry WebBook
Registry NumbersSources
Reaxys:907616Reaxys
CAS:141-05-9ChemIDplus
CAS:141-05-9NIST Chemistry WebBook
Citations