Synonym
β-methyl Itaconate; 4-methyl Itaconate Itaconic; Acid Monomethyl ester; NSC 144957; Monomethyl Itaconate
IUPAC/Chemical Name
4-methoxy-2-methylene-4-oxobutanoic acid
InChi Key
OIYTYGOUZOARSH-UHFFFAOYSA-N
InChi Code
InChI=1S/C6H8O4/c1-4(6(8)9)3-5(7)10-2/h1,3H2,2H3,(H,8,9)
SMILES Code
O=C(C(CC(OC)=O)=C)O
Appearance
To be determined
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
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
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
Preparing Stock Solutions
The following data is based on the
product
molecular weight
144.13
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 |
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).
