624-49-7 Dimethyl fumarate AKSci F927
 
 
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  F927    AKSci Bulk Reagent
Dimethyl fumarate, >99% (GC)
 
Fumaric acid dimethyl ester
IDENTITY
CAS Number:624-49-7
MDL Number:MFCD00064438
MF:C6H8O4
MW:144.13
EINECS:210-849-0
BRN:774590
SPECIFICATIONS & PROPERTIES
Min. Purity Spec:>99% (GC)
Physical Form (at 20°C):Solid
Melting Point:102-106°C
Boiling Point:205°C
Density:1.37
Long-Term Storage:Store long-term in a cool, dry place
DOT/IATA TRANSPORT INFORMATION
Not hazardous material

BIOLOGICAL INFO
Solubility:water:1.6 g/l at 20 °C (68 °F);

REVIEW
 Dimethyl fumarate is a lipophilic, highly mobile molecule in human tissue. As a alpha,beta-unsaturated electrophilic compound, dimethyl fumarate is rapidly attacked by the detoxifying agent glutathione (GSH) in a Michael addition reaction. Dimethyl fumarate is highly reactive: when administered orally, it does not survive long enough to be absorbed into blood without being attacked by GSH. However, part of it is hydrolyzed by esterases to produce monomethylfumarate, which is more resistant. GSH depletion and subsequent induction of the anti-inflammatory stress protein HO-1 is thought to be one of the mechanisms responsible for the immunomodulatory actions of DMF.

REFERENCES
[1]Boyland, E; Chasseaud, LF (1967). Enzyme-catalysed conjugations of glutathione with unsaturated compounds. The Biochemical journal 104 (1): 95-102. PMC 1270549. PMID 6035529
[2] Kubal, Gina; Meyer, David J.; Norman, Richard E.; Sadler, Peter J. (1995). Investigations of Glutathione Conjugation in Vitro by 1H NMR Spectroscopy. Uncatalyzed and Glutathione Transferase-Catalyzed Reactions. Chemical Research in Toxicology 8 (5): 780-91. doi:10.1021/tx00047a019. PMID 7548762.
[3] Schmidt, Thomas J.; Ak, Muharrem; Mrowietz, Ulrich (2007). Reactivity of dimethyl fumarate and methylhydrogen fumarate towards glutathione and N-acetyl-l-cysteine-Preparation of S-substituted thiosuccinic acid esters. Bioorganic & Medicinal Chemistry 15 (1): 333-42. doi:10.1016/j.bmc.2006.09.053. PMID 17049250.
[4] Schmidt, Thomas J.; Aka, Muharrem; Mrowietz, Ulrich (2007). Reactivity of dimethyl fumarate and methylhydrogen fumarate towards glutathione and N-acetyl-l-cysteine-Preparation of S-substituted thiosuccinic acid esters. Bioorganic & Medicinal Chemistry 15 (1): 333-342. doi:10.1016/j.bmc.2006.09.053. PMID 17049250.

GLOBALLY HARMONIZED SYSTEM (GHS)

Pictograms

Signal Word
Warning

Hazard Statements
H312; H315; H317; H319; H335; H411

Precautionary Statements
P261; P264; P271; P272; P273; P280; P302+P352+P312; P304+P340+P312; P305+P351+P338; P333+P313; P337+P313; P362; P391; P403+P233; P405; P501

Current as of April 30, 2024


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⚠️
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CATEGORIES
 APIs and Bioactives > Dermatology


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