DIBUTYL FUMARATE

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-BQYQJAHWSA-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

Molecular Formula	C12H20O4
Molecular Weight	228.2848
Charge	0
Count

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

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 2578
Unknown 2578

PubMed

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

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

Substance Class	Chemical Created by `admin` on `Sat Dec 16 08:08:56 GMT 2023` Edited by `admin` on `Sat Dec 16 08:08:56 GMT 2023`
Record UNII	CQM31Z1NU9
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

DIBUTYL FUMARATE

Systematic Name

English

FUMARIC ACID, DIBUTYL ESTER

Systematic Name

English

NSC-140

Code

English

BUTYL FUMARATE

Systematic Name

English

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

Common Name

English

Code System Code Type Description

NSC

140