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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
176
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Antifungal properties of 2-bromo-3-fluorosuccinic acid esters and related compounds.
1977 Apr
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
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
17
JP2007515543A
9
JP2007515544A
8
JP2007515546A
5
JP2007518861A
2
JP2008520815A
23
JP2009540108A
2
JP2010504257A
15
JP2010538959A
8
JP2011246515A
2
JP2011506638A
3
JP2011508006A
8
JP3587913B2
11
JP4550057B2
3
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 Fri Dec 15 15:24:55 UTC 2023
Edited
by admin
on Fri Dec 15 15:24:55 UTC 2023
Record UNII
4X371TMK9K
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DIBUTYL MALEATE
Systematic Name English
MALEIC ACID, DIBUTYL ESTER
Common Name English
BUTYL MALEATE
Systematic Name English
2-BUTENEDIOIC ACID (Z)-, DIBUTYL ESTER
Common Name English
BUTYL MALEATE [INCI]
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
RC COMONOMER 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 Fri Dec 15 15:24:55 UTC 2023 , Edited by admin on Fri Dec 15 15:24:55 UTC 2023
PRIMARY
PUBCHEM
5271569
Created by admin on Fri Dec 15 15:24:55 UTC 2023 , Edited by admin on Fri Dec 15 15:24:55 UTC 2023
PRIMARY
MESH
C048074
Created by admin on Fri Dec 15 15:24:55 UTC 2023 , Edited by admin on Fri Dec 15 15:24:55 UTC 2023
PRIMARY
RXCUI
1491007
Created by admin on Fri Dec 15 15:24:55 UTC 2023 , Edited by admin on Fri Dec 15 15:24:55 UTC 2023
PRIMARY RxNorm
NSC
6711
Created by admin on Fri Dec 15 15:24:55 UTC 2023 , Edited by admin on Fri Dec 15 15:24:55 UTC 2023
PRIMARY
WIKIPEDIA
Dibutyl maleate
Created by admin on Fri Dec 15 15:24:55 UTC 2023 , Edited by admin on Fri Dec 15 15:24:55 UTC 2023
PRIMARY
FDA UNII
4X371TMK9K
Created by admin on Fri Dec 15 15:24:55 UTC 2023 , Edited by admin on Fri Dec 15 15:24:55 UTC 2023
PRIMARY
ECHA (EC/EINECS)
203-328-4
Created by admin on Fri Dec 15 15:24:55 UTC 2023 , Edited by admin on Fri Dec 15 15:24:55 UTC 2023
PRIMARY
CAS
105-76-0
Created by admin on Fri Dec 15 15:24:55 UTC 2023 , Edited by admin on Fri Dec 15 15:24:55 UTC 2023
PRIMARY
DAILYMED
4X371TMK9K
Created by admin on Fri Dec 15 15:24:55 UTC 2023 , Edited by admin on Fri Dec 15 15:24:55 UTC 2023
PRIMARY
NIH
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