DIBUTYL MALEATE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C12H20O4
Molecular Weight	228.2848
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCCCOC(=O)\C=C/C(=O)OCCCC

InChI

InChIKey=JBSLOWBPDRZSMB-FPLPWBNLSA-N

InChI=1S/C12H20O4/c1-3-5-9-15-11(13)7-8-12(14)16-10-6-4-2/h7-8H,3-6,9-10H2,1-2H3/b8-7-

HIDE SMILES / InChI

Description
Sources: https://www.celanese.com/intermediate-chemistry/products/Dibutyl-Maleate-DBM.aspx | https://www.ncbi.nlm.nih.gov/pubmed/19397629 | https://www.ncbi.nlm.nih.gov/pubmed/26632200 | https://www.ncbi.nlm.nih.gov/pubmed/2936550 | https://www.ncbi.nlm.nih.gov/pubmed/2936545https://www.ncbi.nlm.nih.gov/pubmed/26632200 | http://onlinelibrary.wiley.com/doi/10.1111/j.1468-3083.2009.03429.x/abstract | https://www.ncbi.nlm.nih.gov/pubmed/26632200 |

Dibutyl fumarate (DBF) is a plasticizer compound used in a number of products. However, it is banned from use in consumer products in the European Union after causing a widespread outbreak of dermatitis. The status of DBF as a skin irritant has been confirmed in animal studies. DBF apparently facilitates the trafficking of FITC-presenting CD11c(+) dendritic cells from the skin to draining lymph nodes and increases the cytokine production by draining lymph nodes.

Approval Year

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2596
Unknown 2596

PubMed

Title	Date	PubMed
Structure-activity comparison of the cytotoxic properties of diethyl maleate and related molecules: identification of diethyl acetylenedicarboxylate as a thiol cross-linking agent.	2011-01-14	21105742
Antifungal properties of 2-bromo-3-fluorosuccinic acid esters and related compounds.	1977-04	321785

Patents

Sample Use Guides

In Vivo Use Guide

Female BALB/c mice were subjected to an fluorescein isothiocyanate (FITC) induced contact hypersensitivity experiment. On days 0 and 7, mice were topically sensitized on shaved forelimb skin with a solution of 2% v/v Dibutyl maleate (DBM) in acetone in a volume of 160 micro-L. On day 14 mice were challenged by painting 20 micro-L of 0.5% w/v DBM in acetone on the auricle and monitored for ear swelling at 0, 24, 48, and 72 hours. Sensitization with FITC in the presence of DBM caused an enhanced ear-swelling which peaked at 24 hours.

Route of Administration: Topical

In Vitro Use Guide

Unknown

Name

Type

Language

DIBUTYL MALEATE

Systematic Name

English

RC COMONOMER DBM

Preferred Name

English

MALEIC ACID, DIBUTYL ESTER

Common Name

English

BUTYL MALEATE

Systematic Name

English

2-BUTENEDIOIC ACID (Z)-, DIBUTYL ESTER

Common Name

English

NSC-6711

Code

English

2-BUTENEDIOIC ACID (2Z)-, DIBUTYL ESTER

Common Name

English

VINAVIL CF 5

Brand Name

English

DI-N-BUTYL MALEATE

Common Name

English

2-BUTENEDIOIC ACID (2Z)-, 1,4-DIBUTYL ESTER

Common Name

English

STAFLEX DBM

Brand Name

English

MALEIC ACID DI-N-BUTYL ESTER

Common Name

English

Code System Code Type Description

EPA CompTox

DTXSID3026724