Monomethyl Fumarate | CAS# 2756-87-8 | Anti-Inflammatory

MedKoo Cat#: 558747 | Name: Monomethyl Fumarate

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Monomethyl Fumarate is an anti-inflammatory biochemical.

Chemical Structure

Monomethyl Fumarate

CAS#2756-87-8

Theoretical Analysis

MedKoo Cat#: 558747

Name: Monomethyl Fumarate

CAS#: 2756-87-8

Chemical Formula: C5H6O4

Exact Mass: 130.0266

Molecular Weight: 130.10

Elemental Analysis: C, 46.16; H, 4.65; O, 49.19

Price and Availability

Size	Price	Availability	Quantity
10g	USD 230.00
50g	USD 460.00
100g	USD 745.00

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Synonym

Monomethyl Fumarate

IUPAC/Chemical Name

(2E)-4-methoxy-4-oxobut-2-enoic acid

InChi Key

NKHAVTQWNUWKEO-NSCUHMNNSA-N

InChi Code

InChI=1S/C5H6O4/c1-9-5(8)3-2-4(6)7/h2-3H,1H3,(H,6,7)/b3-2+

SMILES Code

O=C(O)/C=C/C(OC)=O

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>3 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Monomethyl fumarate, an active metabolite of Dimethyl fumarate (DMF), is a potent GPR109A agonist.

In vitro activity:

The objective of this study was to characterize the potential direct neuroprotective effects of dimethyl fumarate (DMF) and its primary metabolite monomethyl fumarate (MMF) on cellular resistance to oxidative damage in primary cultures of central nervous system (CNS) cells and further explore the dependence and function of the nuclear factor (erythroid-derived 2)-like 2 (Nrf2) pathway in this process. DMF or MMF treatment increased cellular redox potential, glutathione, ATP levels, and mitochondrial membrane potential in a concentration-dependent manner. Treating astrocytes or neurons with DMF or MMF also significantly improved cell viability after toxic oxidative challenge in a concentration-dependent manner. Reference: J Pharmacol Exp Ther. 2012 Apr;341(1):274-84. https://pubmed.ncbi.nlm.nih.gov/22267202/

In vivo activity:

MMF (monomethyl fumarate) administered before light exposure mediated dose-dependent neuroprotection in a mouse model of LIR. A single dose of 100 mg/kg MMF fully protected retinal structure and function without side effects. Expression of the Hcar2 receptor and the microglia marker Cd14 were upregulated by LIR, but suppressed by MMF. Reference: Invest Ophthalmol Vis Sci. 2019 Mar 1;60(4):1275-1285. https://pubmed.ncbi.nlm.nih.gov/30924852/

	Solvent	mg/mL	mM
Solubility
	DMF	10.0	76.86
	DMSO	28.7	220.35
	Ethanol	13.3	101.85
	PBS (pH 7.2)	1.0	7.69
	Water	15.0	115.30

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 130.10 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Gola L, Bierhansl L, Hummel N, Korn L, Pawlowski M, Cerina M, Hundehege P, Budde T, König S, Meuth SG, Wiendl H, Kovac S. MMF induces antioxidative and anaplerotic pathways and is neuroprotective in hyperexcitability in vitro. Free Radic Biol Med. 2023 Jan;194:337-346. doi: 10.1016/j.freeradbiomed.2022.12.010. Epub 2022 Dec 13. PMID: 36521578. 2. Scannevin RH, Chollate S, Jung MY, Shackett M, Patel H, Bista P, Zeng W, Ryan S, Yamamoto M, Lukashev M, Rhodes KJ. Fumarates promote cytoprotection of central nervous system cells against oxidative stress via the nuclear factor (erythroid-derived 2)-like 2 pathway. J Pharmacol Exp Ther. 2012 Apr;341(1):274-84. doi: 10.1124/jpet.111.190132. Epub 2012 Jan 20. PMID: 22267202. 3. Xu RC, Miao WT, Xu JY, Xu WX, Liu MR, Ding ST, Jian YX, Lei YH, Yan N, Liu HD. Neuroprotective Effects of Sodium Butyrate and Monomethyl Fumarate Treatment through GPR109A Modulation and Intestinal Barrier Restoration on PD Mice. Nutrients. 2022 Oct 7;14(19):4163. doi: 10.3390/nu14194163. PMID: 36235813; PMCID: PMC9571500. 4. Jiang D, Ryals RC, Huang SJ, Weller KK, Titus HE, Robb BM, Saad FW, Salam RA, Hammad H, Yang P, Marks DL, Pennesi ME. Monomethyl Fumarate Protects the Retina From Light-Induced Retinopathy. Invest Ophthalmol Vis Sci. 2019 Mar 1;60(4):1275-1285. doi: 10.1167/iovs.18-24398. PMID: 30924852; PMCID: PMC6440526.

In vitro protocol:

In vivo protocol:

1. Xu RC, Miao WT, Xu JY, Xu WX, Liu MR, Ding ST, Jian YX, Lei YH, Yan N, Liu HD. Neuroprotective Effects of Sodium Butyrate and Monomethyl Fumarate Treatment through GPR109A Modulation and Intestinal Barrier Restoration on PD Mice. Nutrients. 2022 Oct 7;14(19):4163. doi: 10.3390/nu14194163. PMID: 36235813; PMCID: PMC9571500. 2. Jiang D, Ryals RC, Huang SJ, Weller KK, Titus HE, Robb BM, Saad FW, Salam RA, Hammad H, Yang P, Marks DL, Pennesi ME. Monomethyl Fumarate Protects the Retina From Light-Induced Retinopathy. Invest Ophthalmol Vis Sci. 2019 Mar 1;60(4):1275-1285. doi: 10.1167/iovs.18-24398. PMID: 30924852; PMCID: PMC6440526.

1: Shalmani AA, Ghahremani MH, Jeivad F, Shadboorestan A, Hassanzadeh G, Beh-Pajooh A, Ganbari-Erdi M, Kasirzadeh S, Mojtahedzadeh M, Sabzevari O. Monomethyl fumarate alleviates sepsis-induced hepatic dysfunction by regulating TLR-4/NF-κB signalling pathway. Life Sci. 2018 Dec 15;215:152-158. doi: 10.1016/j.lfs.2018.11.010. Epub 2018 Nov 7. PubMed PMID: 30412724. 2: Mazzola MA, Raheja R, Regev K, Beynon V, von Glehn F, Paul A, Pierre I, Kivisakk P, Weiner HL, Gandhi R. Monomethyl fumarate treatment impairs maturation of human myeloid dendritic cells and their ability to activate T cells. Mult Scler. 2019 Jan;25(1):63-71. doi: 10.1177/1352458517740213. Epub 2017 Nov 6. PubMed PMID: 29106333. 3: Singh D, Reeta KH, Sharma U, Jagannathan NR, Dinda AK, Gupta YK. Neuro-protective effect of monomethyl fumarate on ischemia reperfusion injury in rats: Role of Nrf2/HO1 pathway in peri-infarct region. Neurochem Int. 2019 Jun;126:96-108. doi: 10.1016/j.neuint.2019.03.010. Epub 2019 Mar 14. PubMed PMID: 30880045. 4: Jiang D, Ryals RC, Huang SJ, Weller KK, Titus HE, Robb BM, Saad FW, Salam RA, Hammad H, Yang P, Marks DL, Pennesi ME. Monomethyl Fumarate Protects the Retina From Light-Induced Retinopathy. Invest Ophthalmol Vis Sci. 2019 Mar 1;60(4):1275-1285. doi: 10.1167/iovs.18-24398. PubMed PMID: 30924852; PubMed Central PMCID: PMC6440526. 5: Shi YY, Cui HF, Qin BJ. Monomethyl fumarate protects cerebral hemorrhage injury in rats via activating microRNA-139/Nrf2 axis. Eur Rev Med Pharmacol Sci. 2019 Jun;23(11):5012-5019. doi: 10.26355/eurrev_201906_18093. PubMed PMID: 31210338. 6: Sghaier R, Nury T, Leoni V, Caccia C, Pais De Barros JP, Cherif A, Vejux A, Moreau T, Limem K, Samadi M, Mackrill JJ, Masmoudi AS, Lizard G, Zarrouk A. Dimethyl fumarate and monomethyl fumarate attenuate oxidative stress and mitochondrial alterations leading to oxiapoptophagy in 158N murine oligodendrocytes treated with 7β-hydroxycholesterol. J Steroid Biochem Mol Biol. 2019 Jul 22;194:105432. doi: 10.1016/j.jsbmb.2019.105432. [Epub ahead of print] PubMed PMID: 31344443. 7: Park JB, Park H, Son J, Ha SJ, Cho HS. Structural Study of Monomethyl Fumarate-Bound Human GAPDH. Mol Cells. 2019 Aug 31;42(8):597-603. doi: 10.14348/molcells.2019.0114. PubMed PMID: 31387164; PubMed Central PMCID: PMC6715340.