4-octyl Itaconate

4-octyl Itaconate is a prodrug form of itaconate, an endogenous cellular metabolite produced via decarboxylation of cis-aconitate by the enzyme encoded by IRG1. It is hydrolyzed to itaconate by esterases in C2C12 cells and LPS-activated mouse macrophages where it acts as a regulator of macrophage function with anti-inflammatory properties. 4-octyl Itaconate increases nuclear factor erythroid 2-related factor 2 (Nrf2) protein levels and expression of Nrf2 target genes and enhances LPS-induced Nrf2 stabilization in mouse macrophages. In vivo, 4-octyl itaconate (50 mg/kg) decreases serum levels of IL-1beta and TNF-alpha, increases Nrf2 protein expression, and protects against LPS-induced lethality in wild-type, but not Nrf2 knockout, mice.Formal Name: 2-methylene-butanedioic acid, 4-octyl ester. CAS Number: 3133-16-2. Molecular Formula: C13H22O4. Formula Weight: 242.3. Purity: >98% (mixture of tautomers). Formulation: (Request formulation change), A crystalline solid. Solubility: DMF: 30 mg/ml, DMSO: 30 mg/ml, Ethanol: 30 mg/ml. SMILES: O=C(CC(C(O)=O)=C)OCCCCCCCC. InChi Code: InChI=1S/C13H22O4/c1-3-4-5-6-7-8-9-17-12(14)10-11(2)13(15)16/h2-10H2,1H3,(H,15,16). InChi Key: KBASUIDPDITQHT-UHFFFAOYSA-N.