4-Octyl itaconate
SIGMA/SML2338 - ≥98% (HPLC)
Synonym: β-Monooctyl itaconate; 3-
CAS Number: 3133-16-2
Empirical Formula (Hill Notation): C13H22O4
Molecular Weight: 242.31
Linear Formula: C13H22O4
Product Type: Chemical
| assay | ≥98% (HPLC) |
| color | white to beige |
| form | powder |
| SMILES string | OC(C(CC(OCCCCCCCC)=O)=C)= |
| solubility | DMSO: 2 mg/mL, clear |
| storage condition | protect from light |
| storage temp. | −20°C |
| 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. |
| Biochem/physiol Actions: | 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-induce |
| WGK Germany | WGK 3 |
| Flash Point(F) | Not applicable |
| Flash Point(C) | Not applicable |
| Purity | ≥98% (HPLC) |
| Storage Temp. | −20°C |
| UNSPSC | 12352200 |