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
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+
DescriptionSources: 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 |
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
PubMed
| Title | Date | PubMed |
|---|---|---|
| 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
Sample Use Guides
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
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SUBSTANCE RECORD
