An antioxidant with immunological actions
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Dimethyl fumarate

Item No. 14714

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2E-butenedioic acid, 1,4-dimethyl ester
CAS Number
624-49-7
Synonyms
  • NSC 25942
  • NSC 167432
  • trans-Butenedioic Acid dimethyl ester
Molecular Formula
C6H8O4
Formula Weight
144.1
Purity
≥95%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 10 mg/mlDMF:PBS(pH 7.2)(1:1): 0.5 mg/mlDMSO: 5 mg/mlEthanol: 2 mg/ml
SMILES
COC(/C=C/C(OC)=O)=O
InChi Code
InChI=1S/C6H8O4/c1-9-5(7)3-4-6(8)10-2/h3-4H,1-2H3/b4-3+
InChi Key
LDCRTTXIJACKKU-ONEGZZNKSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    25 g

    $26

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    50 g

    $48

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    100 g

    $70

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    250 g

    $110

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    Product Description

    Dimethyl fumarate is a lipophilic electrophile that has profound effects on oxidative and immunological pathways.1 It rapidly interacts in a Michael addition reaction with glutathione or is metabolized to monomethyl fumarate.1 Dimethyl fumarate at low micromolar levels activates the nuclear factor erythroid 2-related factor 2 (Nrf2), resulting in an antioxidant response featuring heme oxygenase-1 expression and increased glutathione levels.1 It also suppresses the expression of pro-inflammatory cytokines and inhibits angiogenesis.2,3 Through these actions dimethyl fumarate alters the course of psoriasis and may reduce inflammation related to multiple sclerosis.2,4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Albrecht, P., Bouchachia, I., Goebels, N., et al. Effects of dimethyl fumarate on neuroprotection and immunomodulation. J. Neuroinflammation 9, 163 (2012).

    2. Ockenfels, H.M., Schultewolter, T., Ockenfels, G., et al. The antipsoriatic agent dimethylfumarate immunomodulates T-cell cytokine secretion and inhibits cytokines of the psoriatic cytokine network. Br. J. Dermatol. 139(3), 390-395 (1998).

    3. García-Caballero, M., Marí-Beffa, M., Medina, M.A., et al. Dimethylfumarate inhibits angiogenesis in vitro and in vivo: A possible role for its antipsoriatic effect? J. Invest. Dermatol. 131(6), 1347-1355 (2011).

    4. Kappos, L., Gold, R., Miller, D.H., et al. Efficacy and safety of oral fumarate in patients with relapsing-remitting multiple sclerosis: A multicentre, randomised, double-blind, placebo-controlled phase IIb study. Lancet. 372(9648), 1463-1472 (2008).