ETHYL MALEATE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C6H8O4
Molecular Weight	144.1253
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCOC(=O)\C=C/C(O)=O

InChI

InChIKey=XLYMOEINVGRTEX-ARJAWSKDSA-N

InChI=1S/C6H8O4/c1-2-10-6(9)4-3-5(7)8/h3-4H,2H2,1H3,(H,7,8)/b4-3-

HIDE SMILES / InChI

Molecular Formula	C6H8O4
Molecular Weight	144.1253
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	1
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/15479475https://www.ncbi.nlm.nih.gov/pubmed/517824 | https://www.google.com/patents/US3332841

Ethyl maleate is supposed to be a toxic agent. Its administration induced acute aflatoxicosis in goats. Ethyl maleate is also used as a cross-linking agent for the synthesis of polymers.

Approval Year

Conditions

Condition	Modality	Targets	Highest Phase	Product
Psoriasis 84 Sources: https://www.sps.nhs.uk/wp-content/uploads/2015/10/NW-QA246.4-Fumaderm-for-psoriasis-.pdf	Primary		Approved 8429	FUMADERM Approved Use Fumaderm, which contains fumaric acid esters (FAE), is used to treat psoriasis.
Unknown 2578

PubMed

Title	Date	PubMed
Experimentally induced acute aflatoxicosis in goats treated with ethyl maleate, glutathione precursors, or thiosulfate.	1979 Apr	517824
Treatment of psoriasis with fumaric acid esters: results of a prospective multicentre study. German Multicentre Study.	1998 Mar	9580799
In vitro pharmacokinetics of anti-psoriatic fumaric acid esters.	2004 Oct 12	15479475
Use of fumaric acid esters in psoriasis.	2007 Mar-Apr	17456929
Dimethyl fumarate and monoethyl fumarate exhibit differential effects on KEAP1, NRF2 activation, and glutathione depletion in vitro.	2015	25793262

Patents

Sample Use Guides

In Vivo Use Guide

Fumaderm tablets containing ethyl fumarate are given orally. The first 3 weeks, the initial tablet is given using the following schedule: 1 tablet on the first week; 2 tablets on the second week; 3 tablets in the third week. After that, full strength tablets are used: 1 tablet on the fourth week; 2 tablets on the fifth week; 3 tablets on the sixth week; 4 tablets on the 7th week; 5 tablets on the 8th weeks and 6 tablets on the week 9.

Route of Administration: Oral

In Vitro Use Guide

Primary human spinal cord astrocytes were treated for 6 hours with 1, 3, or 6 ug/mL ofa mixture of ethyl fumarate salts (Ca2+, Mg2+, Zn2+). The salts induced the expression of TXNRD1, SRXN1, HMOX1, NQO1 and OSGIN1 genes.

Substance Class	Chemical Created by `admin` on `Sat Dec 16 08:22:27 GMT 2023` Edited by `admin` on `Sat Dec 16 08:22:27 GMT 2023`
Record UNII	AK5N1DQX7U
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ETHYL MALEATE

Systematic Name

English

NSC-11206

Code

English

MONOETHYL (2Z)-2-BUTENEDIOATE

Systematic Name

English

MALEIC ACID, ETHYL ESTER

Common Name

English

NSC-525207

Code

English

2-BUTENEDIOIC ACID (2Z)-, 1-ETHYL ESTER

Systematic Name

English

ETHYL HYDROGEN MALEATE

Systematic Name

English

MONOETHYL MALEATE

Systematic Name

English

Code System Code Type Description

PUBCHEM

5354457