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4-Octyl itaconate

产品编号:4085945
规格:≥98% (HPLC)
CAS NO:3133-16-2
包装规格:5 MG,25 MG
产品类别:进口试剂
品牌:Sigma-Aldrich
优惠价:立即咨询
产品编号包装单位单价(元)国内现货国外库存询价单
40859455 MG1020
408594525 MG3580
产品别名

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

结构式
基本信息
Empirical Formula【经验(实验)分子式】
C13H22O4
Molecular weight
242.31
Application【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

Biochem/physiol Actions【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.
产品性质
Assay【测定】
≥98% (HPLC)
form【形式】
powder
storage condition【储存条件】
protect from light
color【颜色】
white to beige
solubility【溶解性】
DMSO: 2 mg/mL, clear
storage temp.【储存温度】
−20℃
SMILES string
OC(C(CC(OCCCCCCCC)=O)=C)=O
安全信息
Storage Class Code【储存分类代码】
13 - Non Combustible Solids
WGK
WGK 3
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