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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 of DIBUTYL MALEATE

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
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

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

2003
181
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
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
Antifungal properties of 2-bromo-3-fluorosuccinic acid esters and related compounds.
1977-04
Patents

Patents

04032458
2
04123459
2
04412014
2
04420621
2
04485194
2
04497959
4
04547539
4
04563499
2
04828720
3
JP2000219859A
2
JP2000239597A
6
JP2000355672A
2
JP2001002976A
2
JP2001040044A
2
JP2001520247A
4
JP2002538250A
9
JP2002538259A
5
JP2006232709A
2
JP2007502893A
4
JP2007504287A
3
JP2007511658A
11
JP2007515543A
9
JP2007515544A
8
JP2007515546A
5
JP2007518861A
2
JP2008520815A
17
JP2009540108A
2
JP2010504257A
9
JP2010538959A
8
JP2011246515A
2
JP2011506638A
3
JP2011508006A
8
JP3587913B2
11
JP4550057B2
4
JP4805410B2
6
JP4833465B2
6
JPH0198611A
2
JPH03220264A
4
JPH04198350A
2
JPH04209663A
2
JPH04272913A
2
JPH06199966A
2
JPH06200268A
2
JPH08295781A
3
JPH10158111A
2
JPS5787478A
2
JPS58138708A
2
JPS60163227A
2
JPS60184512A
2
JPS6058415A
4
JPS61171775A
4
JPS62160419A
4
JPS62252051A
2
JPS62252052A
2
JPS62277472A
2
JPS6245561A
4
JPS6299720A
4
JPS63170837A
2
JPS63186773A
2
JPS63234263A
2
JPS63258935A
2

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 Mon Mar 31 17:56:56 GMT 2025
Edited
by admin
on Mon Mar 31 17:56:56 GMT 2025
Record UNII
4X371TMK9K
Record Status Validated (UNII)
Record Version
  • Download
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
Created by admin on Mon Mar 31 17:56:56 GMT 2025 , Edited by admin on Mon Mar 31 17:56:56 GMT 2025
PRIMARY
PUBCHEM
5271569
Created by admin on Mon Mar 31 17:56:56 GMT 2025 , Edited by admin on Mon Mar 31 17:56:56 GMT 2025
PRIMARY
MESH
C048074
Created by admin on Mon Mar 31 17:56:56 GMT 2025 , Edited by admin on Mon Mar 31 17:56:56 GMT 2025
PRIMARY
RXCUI
1491007
Created by admin on Mon Mar 31 17:56:56 GMT 2025 , Edited by admin on Mon Mar 31 17:56:56 GMT 2025
PRIMARY RxNorm
NSC
6711
Created by admin on Mon Mar 31 17:56:56 GMT 2025 , Edited by admin on Mon Mar 31 17:56:56 GMT 2025
PRIMARY
WIKIPEDIA
Dibutyl maleate
Created by admin on Mon Mar 31 17:56:56 GMT 2025 , Edited by admin on Mon Mar 31 17:56:56 GMT 2025
PRIMARY
FDA UNII
4X371TMK9K
Created by admin on Mon Mar 31 17:56:56 GMT 2025 , Edited by admin on Mon Mar 31 17:56:56 GMT 2025
PRIMARY
ECHA (EC/EINECS)
203-328-4
Created by admin on Mon Mar 31 17:56:56 GMT 2025 , Edited by admin on Mon Mar 31 17:56:56 GMT 2025
PRIMARY
CAS
105-76-0
Created by admin on Mon Mar 31 17:56:56 GMT 2025 , Edited by admin on Mon Mar 31 17:56:56 GMT 2025
PRIMARY
DAILYMED
4X371TMK9K
Created by admin on Mon Mar 31 17:56:56 GMT 2025 , Edited by admin on Mon Mar 31 17:56:56 GMT 2025
PRIMARY
NIH
NCATS
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