β-Monooctyl itaconate

产品名称：

3133-16-2
4-Octyl itaconate
4-Octyl methylenesuccinate
β-Monooctyl itaconate
3-[(Octan-4-yloxy)carbonyl]but-3-enoate
n-Octyl 3-carboxy-3-butenoate

产品介绍：

产品说明

应用

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

生化/生理作用

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.

基本信息

经验(实验)分子式	C₁₃H₂₂O₄
分子量	242.31

产品性质

测定	≥98% (HPLC)
形式	powder
储存条件	protect from light
颜色	white to beige
溶解性	DMSO: 2 mg/mL, clear
储存温度	−20℃
SMILES string	OC(C(CC(OCCCCCCCC)=O)=C)=O

安全信息

储存分类代码	13 - Non Combustible Solids
WGK	WGK 3
闪点(F)	Not applicable
闪点(C)	Not applicable