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MilliporeSigma

SML4342

MMF prodrug-1c

≥95% (HPLC)

Synonym(s):

(E)-4-Oxo-pent-2-enedioic acid dimethyl ester, 1,5-Dimethyl (2E)-4-oxopent-2-enedioate; (E)-Dimethyl 4-oxopent-2-enedioate, Monomethyl fumarate Prodrug-1c, NRF2 Activator, MMF Prodrug-1c, NFE2L2 Activator MMF, Prodrug-1c

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About This Item

Empirical Formula (Hill Notation):
C7H8O5
CAS Number:
Molecular Weight:
172.14
MDL number:
Assay:
≥95% (HPLC)
Form:
powder
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Quality Segment

assay

≥95% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 2 mg/mL, clear

storage temp.

2-8°C

Biochem/physiol Actions

MMF prodrug-1c is a cell permeable activator of NRF2. A site-specific monomethyl fumarate (MMF) prodrug (1c) achieves targeted delivery of MMF through a peroxide-dependent Baeyer-Villiger oxidation mechanism, selectively activating NRF2 at sites of pathological oxidative stress. Upon oral administration, MMF prodrug-1c rapidly converts to a stable glutathione S-conjugate that circulates until encountering elevated peroxide concentrations (>1 μM H2O2 or >20 μM peroxynitrite) at disease sites, where it releases therapeutic MMF while avoiding indiscriminate NRF2 activation in healthy tissues. At an optimal dose of 350 μmol/kg/day, MMF prodrug-1c demonstrates superior efficacy to conventional MMF delivery in multiple chronic pain models, reversing peripheral neuropathy, osteoarthritis, and chemotherapy-induced neuropathic pain without inducing systemic side effects like glutathione depletion or cutaneous flushing.


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Hazard Classifications

Eye Irrit. 2 - Skin Sens. 1

Storage Class

11 - Combustible Solids

flash_point_f

Not applicable

flash_point_c

Not applicable



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