Catalog Number
ACM141059-1
Product Name
Diethyl-2-butenedioate
Category
Polymers; Plasticizers
IUPAC Name
diethyl (Z)-but-2-enedioate
Molecular Weight
172.18g/mol
Canonical SMILES
CCOC(=O)C=CC(=O)OCC
InChI
InChI=1S/C8H12O4/c1-3-11-7(9)5-6-8(10)12-4-2/h5-6H,3-4H2,1-2H3/b6-5-
InChI Key
IEPRKVQEAMIZSS-WAYWQWQTSA-N
Melting Point
-3.65 °C;1-2°C
Application
Diethyl-2-butenedioate primarily serves as an important intermediate in organic synthesis. This colorless liquid, with a boiling point of 225°C, is known for its role in cycloaddition reactions, particularly as a dienophile in Diels-Alder-type reactions. While it is insoluble in water, it readily dissolves in ethanol and ether. Although its fruity, banana-citrus aroma makes it distinct, regulatory restrictions in places like the EU have limited its use in fragrances due to potential sensitization. Beyond its synthetic applications, Diethyl-2-butenedioate has been studied for its biological activity, notably its ability to modulate glutathione levels and affect cancer-related pathways, making it a compound of interest in biochemical research.
Covalently-Bonded Unit Count
1
EC Number
205-451-9;615-281-0
Exact Mass
172.073559g/mol
MeSH Entry Terms
diethyl maleate;diethyl maleic acid diester;diethylmaleate;ethyl hydrogen maleate;ethyl maleate;maleic acid diethyl ester;maleic acid, ethyl ester;monoethyl maleate
Monoisotopic Mass
172.073559g/mol