A copolymerization reagent and an active metabolite of SCD-153
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Monomethyl Itaconate

Item No. 43263

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2-methylene-butanedioic acid, 4-methyl ester
CAS Number
7338-27-4
Synonyms
  • β-methyl Itaconate
  • 4-methyl Itaconate
  • Itaconic Acid Monomethyl ester
  • NSC 144957
Molecular Formula
C6H8O4
Formula Weight
144.1
Purity
≥95%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMSO: Sparingly soluble: 1-10 mg/mlEthanol: Sparingly soluble: 1-10 mg/mlPBS (pH 7.2): Sparingly soluble: 1-10 mg/ml
SMILES
O=C(C(CC(OC)=O)=C)O
InChi Code
InChI=1S/C6H8O4/c1-4(6(8)9)3-5(7)10-2/h1,3H2,2H3,(H,8,9)
InChi Key
OIYTYGOUZOARSH-UHFFFAOYSA-N
Origin
Synthetic
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    25 g

    $99

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    50 g

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    100 g

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    500 g

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    Product Description

    Monomethyl itaconate is a copolymerization reagent and an active metabolite of the prodrug SCD-153.1,2,3 It has also been found in U. maydis.4 Monomethyl itaconate has been used in the generation of copolymeric hydrogels for the formation of methotrexate-containing polymer disks.2 Monomethyl itaconate has been used in the synthesis of thrombin inhibitors.5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. del C Pizzaro, G., Marambio, O.G., Jeria-Orell, M., et al. Preparation, characterization, and thermal properties of hydrophilic copolymers: p-Chlorophenylmaleimides with hydroxylethyl methacrylate and β-methyl itaconate. Polym. Int. 62(6), 843-848 (2007).

    2. Teijón, C., Guerrero, S., Olmo, R., et al. Swelling properties of copolymeric hydrogels of poly(ethylene glycol) monomethacrylate and monoesters of itaconic acid for use in drug delivery. J. Biomed. Mater. Res. B Appl. Biomater. 91(2), 716-726 (2009).

    3. Tsai, J., Gori, S., Alt, J., et al. Topical SCD-153, a 4-methyl itaconate prodrug, for the treatment of alopecia areata. PNAS Nexus 2(1), pgac297 (2022).

    4. Wu, H.-C., His, H.-Y., Hsiao, G., et al. Chemical constituents and bioactive principles from the Mexican truffle and fermented products of the derived fungus Ustilago maydis MZ496986. J. Agric. Food Chem. 71(2), 1122-1131 (2023).

    5. Thorstensson, F., Kvarnström, I., Musil, D., et al. Synthesis of novel thrombin inhibitors. Use of ring-closing metathesis reactions for synthesis of P2 cyclopentene- and cyclohexenedicarboxylic acid derivatives. J. Med. Chem. 46(7), 1165-1179 (2003).