| Size | Price | |
|---|---|---|
| Other Sizes |
Purity: ≥98%
| Targets |
Metabolite of insecticide
The primary targets of Diethyl fumarate are not well-defined, as it is primarily used as a chemical intermediate and flavoring agent. As a diester of fumaric acid, it may be hydrolyzed to fumaric acid, which is an intermediate in the citric acid cycle and can activate the Nrf2 pathway, leading to antioxidant and anti-inflammatory effects. The compound may also interact with various enzymes involved in ester hydrolysis and metabolism. These characteristics make it relevant for research in metabolism, polymer chemistry, and pharmaceutical synthesis. |
|---|---|
| ln Vitro |
diethyl fumarate, a reputed skin irritant, is much more volatile than malathion and is readily lost by volatilization from cloth and dusts used to control body lice, Pediculus humanus humanus L., the rate of loss was determined. The electron-capture method proved to be operable at the picogram level for diethyl fumarate and in the low nanogram range for malathion [1].
In vitro, Diethyl fumarate is used as a chemical intermediate in organic synthesis. It is employed in the synthesis of various pharmaceuticals, agrochemicals, and polymers. The compound’s hydrolysis to fumaric acid can be studied using esterase enzymes. Its antimicrobial and antioxidant properties have been evaluated in various assays. These in vitro activities support its use in synthetic chemistry, pharmaceutical research, and polymer science. |
| ln Vivo |
The contact urticariagenic properties of diethyl fumarate were studied using the guinea pig ear swelling assay and by open application on the human upper back skin. Diethyl fumarate caused non-immunologic contact urticaria in both human and guinea pig skin, and the reactions exhibited similar dose dependency and timing of maximal response [2].
In vivo, Diethyl fumarate is hydrolyzed to fumaric acid and ethanol following absorption. Fumaric acid is an intermediate in the citric acid cycle and may have metabolic effects. Fumaric acid esters, including dimethyl fumarate, are used clinically for the treatment of psoriasis and multiple sclerosis. However, diethyl fumarate itself is not used as a therapeutic agent. The compound is used as a flavoring agent and fragrance ingredient in consumer products at approved concentrations. |
| Enzyme Assay |
In vitro enzyme assays for Diethyl fumarate involve studying its hydrolysis by esterases. The compound is incubated with purified esterases or tissue homogenates at concentrations ranging from 0.1-1000 μM, and the formation of fumaric acid and ethanol is monitored by HPLC or GC. Kinetic parameters are determined. Antimicrobial activity is assessed using broth microdilution methods. Antioxidant activity is evaluated using DPPH or ABTS assays. All assays include appropriate controls and reference compounds.
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| Cell Assay |
In vitro cell-based assays for Diethyl fumarate are limited, as the compound is primarily used as a chemical intermediate. Cytotoxicity studies may be performed to assess safety. Cells are treated with compound concentrations ranging from 0.1-1000 μM for 24-72 hours. Cell viability is assessed using MTT assays. The compound’s effects on cellular metabolism may be evaluated. Experiments include vehicle controls.
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| Animal Protocol |
In vivo animal studies with Diethyl fumarate are limited to safety and toxicology assessments for regulatory approval as a flavoring agent. The compound is administered via oral gavage at various doses. Toxicity and irritation potential are evaluated. Each group consists of 6-10 animals with appropriate controls.
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| ADME/Pharmacokinetics |
Pharmacokinetic properties of Diethyl fumarate include its rapid hydrolysis to fumaric acid and ethanol following absorption. As a small, lipophilic ester, it is expected to have good oral bioavailability. Fumaric acid is metabolized through the citric acid cycle to CO₂ and water. Ethanol is metabolized by alcohol dehydrogenase. Elimination occurs primarily as CO₂ and water. Detailed PK parameters are available from safety studies.
|
| Toxicity/Toxicokinetics |
Interactions
To investigate the mechanism of non-immune contact urticaria (NICU), this study examined the effects of 1 g + 1 g acetylsalicylic acid (ASA) on contact reactions to methyl nicotinic acid, diethyl fumarate, benzoic acid, cinnamic acid, cinnamaldehyde, and dimethyl sulfoxide in 21 subjects. Erythema and edema were observed visually, and skin blood flow was monitored using laser Doppler flowmetry. ASA significantly inhibited erythema induced by the above six substances and edema induced by all substances except dimethyl sulfoxide. Its mechanism of action may be the inhibition of prostaglandin biosynthesis by ASA. Therefore, to avoid false negative results, nonsteroidal anti-inflammatory drugs (NSAIDs) should not be used during testing in the neonatal intensive care unit (NICU). Non-human Toxicity Oral LD50 in rats: 1780 mg/kg Toxicological data for Diethyl fumarate indicate that it is generally recognized as safe for use as a flavoring agent at approved concentrations. No significant toxicity has been reported at typical exposure levels. However, as with all chemicals, appropriate safety precautions should be taken during handling. |
| References | |
| Additional Infomation |
Diethyl fumarate is a weight-loss drug formed by the condensation of fumaric acid and ethanol. It is a metabolite functionally related to fumaric acid.
See also: Diethyl maleate (note moved here). Drug Warning Monoethyl fumarate has genuine anti-psoriatic activity, but its toxicity is too high for clinical application. Experimental studies have confirmed that the above-mentioned fumarate esters inhibit nucleic acid and protein synthesis in PHA-stimulated human lymphocytes. Diethyl fumarate is a diester of fumaric acid used as a flavoring agent, fragrance ingredient, and chemical intermediate in the synthesis of pharmaceuticals, agrochemicals, and polymers. It is a precursor to fumaric acid, which is an intermediate in the citric acid cycle. Not approved as a therapeutic agent; intended for research and commercial applications. |
| Molecular Formula |
C₈H₁₂O₄
|
|---|---|
| Molecular Weight |
172.18
|
| Exact Mass |
172.073
|
| CAS # |
623-91-6
|
| Related CAS # |
26298-06-6
|
| PubChem CID |
638144
|
| Appearance |
Colorless to light yellow liquid
|
| Density |
1.1±0.1 g/cm3
|
| Boiling Point |
214.0±0.0 °C at 760 mmHg
|
| Melting Point |
41641ºC
|
| Flash Point |
93.3±0.0 °C
|
| Vapour Pressure |
0.2±0.4 mmHg at 25°C
|
| Index of Refraction |
1.443
|
| LogP |
1.68
|
| Hydrogen Bond Donor Count |
0
|
| Hydrogen Bond Acceptor Count |
4
|
| Rotatable Bond Count |
6
|
| Heavy Atom Count |
12
|
| Complexity |
164
|
| Defined Atom Stereocenter Count |
0
|
| SMILES |
O(C(/C(/[H])=C(\[H])/C(=O)OC([H])([H])C([H])([H])[H])=O)C([H])([H])C([H])([H])[H]
|
| InChi Key |
IEPRKVQEAMIZSS-AATRIKPKSA-N
|
| InChi Code |
InChI=1S/C8H12O4/c1-3-11-7(9)5-6-8(10)12-4-2/h5-6H,3-4H2,1-2H3/b6-5+
|
| Chemical Name |
diethyl (E)-but-2-enedioate
|
| Synonyms |
Diethyl fumarate; Diethyl fumarate
|
| HS Tariff Code |
2934.99.9001
|
| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
|
| Solubility (In Vitro) |
DMSO : ~140 mg/mL (~813.10 mM)
H2O : ~3 mg/mL (~17.42 mM) |
|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 3.5 mg/mL (20.33 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 35.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 3.5 mg/mL (20.33 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 35.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. View More
Solubility in Formulation 3: ≥ 3.5 mg/mL (20.33 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. Solubility in Formulation 4: 100 mg/mL (580.79 mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with ultrasonication. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 5.8079 mL | 29.0394 mL | 58.0788 mL | |
| 5 mM | 1.1616 mL | 5.8079 mL | 11.6158 mL | |
| 10 mM | 0.5808 mL | 2.9039 mL | 5.8079 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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