Diethyl maleate is an organic compound with the
CAS Registry number 141-05-9. It is chemically a maleate ester with the formula C8H12O4. It is a colorless liquid at room temperature. It has the
IUPAC name of diethyl (Z)-but-2-enedioate.[1]
One of the key uses for the compound is in production of the
pesticideMalathion.[5] It has also been used medically as a chemical depletory of
glutathione.[6] It has been studied extensively with regard to renal function.[7] Other medical uses include treatment of breast
cancer and its monitoring with
Positron Emission Tomography.[8] It is also used as a food additive[9] and has Food and Drug Administration clearance for indirect food contact.
In synthetic organic chemistry it is a
dienophile and used in the
Diels-Alder reaction.
With the invention of
polyaspartic technology the material also found another use. With this technology an amine is reacted with a dialkyl maleate - usually diethyl maleate - utilizing the
Michael addition reaction.[10][11] These products are then used in
coatings,
adhesives,
sealants and
elastomers.[12]
^PubChem.
"Diethyl maleate". pubchem.ncbi.nlm.nih.gov.
Archived from the original on 2022-01-29. Retrieved 2022-02-22.
^Uthus, Eric O. (1994-12-01). "Diethyl maleate, an in vivo chemical depletor of glutathione, affects the response of male and female rats to arsenic deprivation". Biological Trace Element Research. 46 (3): 247–259.
doi:
10.1007/BF02789300.
ISSN1559-0720.
PMID7702979.
^Davis, Mary E.; Berndt, William O.; Mehendale, Harihara M. (1986-05-01). "Effects of cysteine and diethylmaleate pretreatments on renal function and response to a nephrotoxicant". Archives of Toxicology. 59 (1): 7–11.
doi:
10.1007/BF00263949.
ISSN1432-0738.
PMID3741149.
^Čolović, Milena; Yang, Hua; Merkens, Helen; Colpo, Nadine; Bénard, François; Schaffer, Paul (2019-12-01). "Non-invasive Use of Positron Emission Tomography to Monitor Diethyl maleate and Radiation-Induced Changes in System xC− Activity in Breast Cancer". Molecular Imaging and Biology. 21 (6): 1107–1116.
doi:
10.1007/s11307-019-01331-8.
ISSN1860-2002.
PMID30838549.
^US 5243012, Wicks, Douglas A. & Yeske, Philip E., "Polyurea coating compositions having improved pot lives", published 1993-09-07, assigned to Miles Inc.
^EP 403921, Zwiener, Christian; Pedain, Josef & Kahl, Lothar et al., "Process for the preparation of coatings", published 1990-12-27, assigned to
Bayer AG
^Howarth, G. A (2003). "Polyurethanes, polyurethane dispersions and polyureas: Past, present and future". Surface Coatings International Part B: Coatings Transactions. 86 (2): 1110–1118.
doi:
10.1007/BF02699621.