An active metabolite of dimethyl fumarate
Related Products
Parent Compound(s)
14714Dimethyl fumarate
Pro-drug Form(s)
29111Diroximel Fumarate
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Monomethyl fumarate

Item No. 27813

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2E-butenedioic acid, 1-methyl ester
CAS Number
2756-87-8
Synonyms
  • Fumaric Acid monomethyl ester
Molecular Formula
C5H6O4
Formula Weight
130.1
Purity
≥98%
Formulation
A solid
Solubility(Learn about Variance in Solubility)
DMF: 10 mg/mlDMSO: 10 mg/mlEthanol: 0.5 mg/mlPBS (pH 7.2): 1 mg/ml
SMILES
OC(/C=C/C(OC)=O)=O
InChi Code
InChI=1S/C5H6O4/c1-9-5(8)3-2-4(6)7/h2-3H,1H3,(H,6,7)/b3-2+
InChi Key
NKHAVTQWNUWKEO-NSCUHMNNSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    10 g

    $69

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    250 g

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    Cayman Chemical
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    Product Description

    Monomethyl fumarate is an active metabolite of the immune modulator dimethyl fumarate (Item No. 14714) that is rapidly formed from dimethyl fumarate by hydrolysis.1 It is an agonist of the hydroxycarboxylic acid 2 (HCA2) receptor/GPR109A with an EC50 value of 9.4 µM for inducing calcium accumulation in CHO cells expressing the receptor.2 Monomethyl fumarate reduces neutrophil adhesion to endothelial cells stimulated with TNF, decreases CXCL2-directed neutrophil migration, and increases the expression of the Nrf2 target gene NQO1 in wild-type but not HCA2-/- macrophages.3 It inhibits proliferation and induces differentiation in keratinocytes, as well as decreases the levels of TNF-α induced by phorbol 12-myristate 13-acetate (TPA; Item No. 10008014) in keratinocytes when used at a concentration of 1 mM.4 Monomethyl fumarate (1 mg/day) reduces symptoms of experimental autoimmune encephalomyelitis (EAE) in mice and isolated natural killer cells from these mice induced cytotoxicity in previously isolated immature and mature dendritic cells.5 Formulations containing monomethyl fumarate have been used in the treatment of multiple sclerosis.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Dibbert, S., Clement, B., Skak-Nielsen, T., et al. Detection of fumarate-glutathione adducts in the portal vein blood of rats: Evidence for rapid dimethylfumarate metabolism. Arch. Dermatol. Res. 305(5), 447-451 (2013).

    2. Tang, H., Lu, J.Y.-L., Zheng, X., et al. The psoriasis drug monomethylfumarate is a potent nicotinic acid receptor agonist. Biochem. Biophys. Res. Commun. 375(4), 562-565 (20008).

    3. Chen, H., Assmann, J.C., Krenz, A., et al. Hydroxycarboxylic acid receptor 2 mediates dimethyl fumarate’s protective effect in EAE. J. Clin. Invest. 124(5), 2188-2192 (2014).

    4. Helwa, I., Patel, R., Karempelis, P., et al. The antipsoriatic agent monomethylfumarate has antiproliferative, prodifferentiative, and anti-inflammatory effects on keratinocytes. J. Pharmacol. Exp. Ther. 352(1), 90-97 (2015).

    5. Al-Jaderi, Z., and Maghazachi, A.A. Vitamin D₃ and monomethyl fumarate enhance natural killer cell lysis of dendritic cells and ameliorate the clinical score in mice suffering from experimental autoimmune encephalomyelitis. Toxins (Basel) 7(11), 4730-4744 (2015).