SML2338

4-Octyl itaconate

≥98% (HPLC)

• Synonyme(s) : β-Monooctyl itaconate, 3-[(Octan-4-yloxy)carbonyl]but-3-enoate, 4-Octyl methylenesuccinate, n-Octyl 3-carboxy-3-butenoate
• Formule empirique (notation de Hill): C₁₃H₂₂O₄
• Numéro CAS: 3133-16-2
• Poids moléculaire : 242.31
• Code UNSPSC : 51111800
• Nomenclature NACRES : NA.77

Propriétés

• Essai: ≥98% (HPLC)
• Forme: powder
• Conditions de stockage: protect from light
• Couleur: white to beige
• Solubilité: DMSO: 2 mg/mL, clear
• Température de stockage: −20°C
• Chaîne SMILES: 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
• Clé InChI: 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

Actions biochimiques/physiologiques

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.

Cell-permeable itaconate derivative that decreases cytokine production and is protective against lipopolysaccharide-induced lethality in vivo.

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.

Informations sur la sécurité

• Code de la classe de stockage: 11 - Combustible Solids
• Classe de danger pour l'eau (WGK): WGK 3
• Point d'éclair (°F): Not applicable
• Point d'éclair (°C): Not applicable