Dimethyl fumarate - Moligand™, ≥99% , CAS No.624-49-7

CAS: 624-49-7 Cat. No.: D106460 Molecular Weight: 144.13 Beilstein Registry Number: 774590 EC Number: 210-849-0

GRADE & PURITY Moligand™, ≥99%

Synonyms

Dimethylfumarate | BG-12 | (E)-Dimethyl fumarate | Boletic acid dimethyl ester | Methyl fumarate | Dimethyl (E)-but-2-enedioate | Fumaric acid dimethyl ester | Panaclar | Fumaric acid, dimethyl ester | Dimethyl fumarate | Tecfidera | Fumaderm

Storage

Room temperature

Shipped In

Normal

Overview

application：

Dimethyl fumarate can be used:In the preparation of an adduct [dimethyl-(+)-(11R,12R)-9,10-dihydro-9,10-ethanoanthracene-11,12-dicarboxylate].As a ligand in the synthesis of Ni(II)-based catalytic system applicable in the Negishi alkylations of N-sulfonyl aziridines with organozinc reagents.As a ligand to synthesize zerovalent ruthenium metal complex namely Ru(η6-1,3,5-cyclooctatriene)(η2-dimethyl fumarate)2.Dimethyl fumarate acts as an immunomodulator. It is also used in cycloaddition reactions involving ylides, benzenes and amino acids. It is added to food grains,tobacco,leather and preservation.

Specifications

Synonyms

Dimethylfumarate | BG-12 | (E)-Dimethyl fumarate | Boletic acid dimethyl ester | Methyl fumarate | Dimethyl (E)-but-2-enedioate | Fumaric acid dimethyl ester | Panaclar | Fumaric acid, dimethyl ester | Dimethyl fumarate | Tecfidera | Fumaderm

Specifications & Purity

Moligand™, ≥99%

Biochemical and Physiological Mechanisms

Dimethyl fumarate is a nuclear factor (erythroid-derived)-like 2 (Nrf2) pathway activator. Dimethyl fumarate induces upregulation of antioxidant gene expression. Dimethyl fumarate displays cytoprotective effects in human spinal cord astro

Storage

Room temperature

Shipped In

Normal

Grade

Moligand™

Purity

≥99%

Names and Identifiers

• Canonical Smiles: COC(=O)C=CC(=O)OC
• IUPAC Name: dimethyl (E)-but-2-enedioate
• InChIKey: LDCRTTXIJACKKU-ONEGZZNKSA-N
• INCHI: 1S/C6H8O4/c1-9-5(7)3-4-6(8)10-2/h3-4H,1-2H3/b4-3+
• Isomeric SMILES: COC(=O)/C=C/C(=O)OC
• WGK Germany: 1
• RTECS: EM6125000
• Molecular Weight: 144.13
• Beilstein: 774590
• Reaxy-Rn: 8137488
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=8137488&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Lipids and lipid-like molecules
    • Class Fatty Acyls
      • Subclass Fatty acid esters

• Kingdom: Organic compounds
• Superclass: Lipids and lipid-like molecules
• Class: Fatty Acyls
• Subclass: Fatty acid esters
• Intermediate Tree Nodes: Not available
• Direct Parent: Fatty acid esters
• Alternative Parents: Dicarboxylic acids and derivatives Methyl esters Enoate esters Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aliphatic acyclic compounds
• Substituents: Fatty acid ester - Dicarboxylic acid or derivatives - Alpha,beta-unsaturated carboxylic ester - Enoate ester - Methyl ester - Carboxylic acid ester - Carboxylic acid derivative - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Carbonyl group - Aliphatic acyclic compound
• Description: This compound belongs to the class of organic compounds known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid.
• External Descriptors: diester - methyl ester - enoate ester

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

EGFR Tclin Epidermal growth factor receptor erbB1 (33727 Activities)

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AR Tclin Androgen Receptor (11781 Activities)

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GABRA1 Tclin GABA receptor alpha-1 subunit (399 Activities)

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CNR1 Tclin Cannabinoid CB1 receptor (20913 Activities)

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PTGS1 Tclin Cyclooxygenase-1 (9233 Activities)

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SLC6A2 Tclin Norepinephrine transporter (10102 Activities)

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ADRA1A Tclin Alpha-1a adrenergic receptor (8359 Activities)

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PTGS2 Tclin Cyclooxygenase-2 (13999 Activities)

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HRH1 Tclin Histamine H1 receptor (7573 Activities)

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OPRM1 Tclin Mu opioid receptor (19785 Activities)

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PPARG Tclin Peroxisome proliferator-activated receptor gamma (15191 Activities)

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OPRD1 Tclin Delta opioid receptor (15096 Activities)

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OPRK1 Tclin Kappa opioid receptor (16155 Activities)

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SLC6A3 Tclin Dopamine transporter (10535 Activities)

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GRIN1 Tclin Glutamate (NMDA) receptor subunit zeta 1 (122 Activities)

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KCNH2 Tclin HERG (29587 Activities)

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PDE3A Tclin Phosphodiesterase 3A (3309 Activities)

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SLC29A1 Tclin Equilibrative nucleoside transporter 1 (1711 Activities)

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ERBB2 Tclin Receptor protein-tyrosine kinase erbB-2 (7851 Activities)

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ADRA2B Tclin Alpha-2b adrenergic receptor (4412 Activities)

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ADRA2C Tclin Alpha-2c adrenergic receptor (4876 Activities)

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CHRM3 Tclin Muscarinic acetylcholine receptor M3 (7750 Activities)

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HTR2B Tclin Serotonin 2b (5-HT2b) receptor (10323 Activities)

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EDNRA Tclin Endothelin receptor ET-A (5008 Activities)

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ADORA2A Tclin Adenosine A2a receptor (16305 Activities)

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ADORA3 Tchem Adenosine A3 receptor (15931 Activities)

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BDKRB2 Tclin Bradykinin B2 receptor (3970 Activities)

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Associated Targets(non-human)

Npy1r Neuropeptide Y receptor type 1 (8 Activities)

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Cckar Cholecystokinin A receptor (90 Activities)

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Pde4d Phosphodiesterase 4D (4 Activities)

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Hdac6 Histone deacetylase 6 (222 Activities)

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rep Replicase polyprotein 1ab (378 Activities)

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Trichophyton mentagrophytes (4846 Activities)

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Nfe2l2 Nuclear factor erythroid 2-related factor 2 (214 Activities)

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Mechanisms of Action

Chemical and Physical Properties

• Solubility: Soluble in water (1.6 mg/ml at 20°C), methanol (30-36 mg/ml), ethanol (10 mg/ml at 25°C), DMSO (29 mg/ml at 25°C), and DMF (~12 mg/ml).
• Boil Point(°C): 193°C
• Melt Point(°C): 103—104°C
• Molecular Weight: 144.120 g/mol
• XLogP3: 0.700
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 144.042 Da
• Monoisotopic Mass: 144.042 Da
• Topological Polar Surface Area: 52.600 Ų
• Heavy Atom Count: 10
• Formal Charge: 0
• Complexity: 141.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 1
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 1
• Covalently-Bonded Unit Count: 1

References

1. Caihong Wang, Yong Liu, Fengshen Han, Yongzhe Han, Tianyu Liu, Haitao Ren, Xu Han.  (2023)  Nitrogen-doped carbocatalyst activated persulfate (PS) for oxidation polymerization of bisphenol A (BPA): importance of nonradical activation of PS.  PHYSICAL CHEMISTRY CHEMICAL PHYSICS,  25  (19): (13716-13727).  [PMID:37158256] [10.1039/D3CP00659J]

2. Shao-Qi Zhi, Jun-Yuan Zhang, Song-Hai Wu, Wen-Shuang Zhu, Yu-Dong Shan, Yong Liu, Xu Han.  (2023)  Oxidative Desulfurization of Benzothiophene by Persulfate and Cu-Loaded g-C3 N4 via the Polymerization Pathway.  INDUSTRIAL & ENGINEERING CHEMISTRY RESEARCH,      [PMID:] [10.1021/acs.iecr.2c04484]

3. Xin‐Lin Zhang, Ting‐Yu Wang, Zheng Chen, Hong‐Wei Wang, Yong Yin, Lian Wang, Yong Wang, Biao Xu, Wei Xu.  (2022)  HMGB1‐Promoted Neutrophil Extracellular Traps Contribute to Cardiac Diastolic Dysfunction in Mice.  Journal of the American Heart Association,      [PMID:35156391] [10.1161/JAHA.121.023800]

4. Tian-Yu Liu, Cong Wang, Yong-Zhe Han, Chang Bai, Hai-Tao Ren, Yong Liu, Xu Han.  (2022)  Oxidative polymerization of bisphenol A (BPA) via H-abstraction by Bi2.15WO6 and persulfate: Importance of the surface complexes.  CHEMICAL ENGINEERING JOURNAL,      [PMID:] [10.1016/j.cej.2022.134816]

5. Chang Bai, Yong Liu, Cong Wang, Xiao-Cong Zhang, Jia-Xuan Wu, Hai-Tao Ren, Xu Han.  (2021)  Conversion of aniline contaminant to valuable polyaniline polymers from wastewater under alkaline conditions.  Molecular Catalysis,      [PMID:] [10.1016/j.mcat.2021.111430]

6. Xiao-Cong Zhang, Song-Hai Wu, Shao-Yi Jia, Cong Wang, Shi-Wei Sun, Xiang-Ming Wang, Zi-He Meng, Yi-Ying Lin, Yong Liu, Hai-Tao Ren, Xu Han.  (2020)  Turning thiophene contaminant into polymers from wastewater by persulfate and CuO.  CHEMICAL ENGINEERING JOURNAL,      [PMID:] [10.1016/j.cej.2020.125351]

7. Haiyan Zhu, Yijing Yang, Yenan Duan, Xin Zheng, Zixiong Lin, Jie Zhou.  (2024)  Nrf2/FSP1/CoQ10 axis-mediated ferroptosis is involved in sodium aescinate-induced nephrotoxicity.  ARCHIVES OF BIOCHEMISTRY AND BIOPHYSICS,      [PMID:39033970] [10.1016/j.abb.2024.110100]

8. Xin Zheng, Xinyi Tang, Yinan Xu, Haiyan Zhu, Lianwei Zhong, Chen Chen, Jiajun Cui, Jie Zhou.  (2025)  Sodium aescinate induces hepatotoxicity through apoptosis and ferroptosis by inhibiting the Nrf2/CTH pathway.  JOURNAL OF ETHNOPHARMACOLOGY,      [PMID:40064321] [10.1016/j.jep.2025.119608]