SML2338

4-Octyl itaconate

≥98% (HPLC)

• Synonym(s): β-Monooctyl itaconate, 3-[(Octan-4-yloxy)carbonyl]but-3-enoate, 4-Octyl methylenesuccinate, n-Octyl 3-carboxy-3-butenoate
• Empirical Formula (Hill Notation): C₁₃H₂₂O₄
• CAS Number: 3133-16-2
• Molecular Weight: 242.31
• UNSPSC Code: 12352200

Properties

• Assay: ≥98% (HPLC)
• form: powder
• storage condition: protect from light
• color: white to beige
• solubility: DMSO: 2 mg/mL, clear
• storage temp.: −20°C
• SMILES string: OC(C(CC(OCCCCCCCC)=O)=C)=O
• InChI: 1S/C13H22O4/c1-4-6-8-11(7-5-2)17-13(16)10(3)9-12(14)15/h11H,3-9H2,1-2H3,(H,14,15)/p-1
• InChI key: GIRJEIMINMHXQS-UHFFFAOYSA-M

Description

Application

4-Octyl itaconate has been used:

• to study its anti-inflammatory effects in macrophages
• to treat bone-marrow-derived macrophages (BMDMs) for BMDM stimulation with nuclear factor-erythroid factor 2-related factor 2 (NRF2)-activating carboxylic acid compounds
• to study its effects on collagen1 expression in systemic Sclerosis (SSc) dermal fibroblasts

Biochem/physiol Actions

4-Octyl itaconate (4-OI) possesses anti-inflammatory effects. It can obstruct glyceraldehyde 3-phosphate dehydrogenase (GAPDH) and glycolysis in macrophages. It can be a good substitute to itaconate due to its thiol reactivity. The electrophilic α and β-unsaturated moieties of 4-OI might help to alkylate the thiol in cysteine residues of proteins through Michael reaction.

The endogenous metabolite itaconate has recently emerged as a regulator of macrophage function. 4-Octyl itaconate is a cell-permeable itaconate derivative that decreases cytokine production and is protective against lipopolysaccharide-induced lethality in vivo. Esterases in mouse myoblast cells and macrophages hydrolyze it to itaconate, which alkylates cysteine residues on KEAP1, allowing the transcription factor Nrf2 to increase the expression of anti-oxidant and anti-inflammatory downstream genes.

Safety Information

• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable