CAS 3133-16-2; β-monooctyl itaconate; 4-octyl itaconate

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CAS:

3133-16-2

分子式:

C₁₃H₂₂O₄

分子量:

242.31

中文名称:

β-monooctyl itaconate

英文名称:

4-octyl itaconate

4-octyl methylenesuccinate

3-[(octan-4-yloxy)carbonyl]but-3-enoate

n-octyl 3-carboxy-3-butenoate

用途:

4-Octyl Itaconate 是一种可透过细胞的 Itaconate 衍生物。Itaconate 是一种抗炎代谢产物，通过 KEAP1 的烷基化而活化 Nrf2。

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货号

品牌

产品名称

规格

包装、参考价格

O879644

MACKLIN

4-Octyl Itaconate

99%

412元/50mg; 625元/100mg; 1135元/250mg; 3350元/1g; 9860元/5g;

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储存：2-8℃
状态：白色到灰白色固体

O795707

MACKLIN

4-Octyl Itaconate

10mM in DMSO

268元/1ml;

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储存：-20°C
状态：液体

SML2338

Sigma-Aldrich

4-Octyl itaconate

≥98% (HPLC)

887.5元/5 MG; 3586.11元/25 MG;

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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

544397

Fluorochem

4-Octyl itaconate

98%

7480元/250mg; 18568元/1g;

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基本信息

CAS Number	3133-16-2
MDL Number	MFCD31706409

安全信息

图形或危害标志
危险性说明	H302: Harmful if swallowed. H315: Causes skin irritation. H319: Causes serious eye irritation. H335: May cause respiratory irritation.
防范说明	P233: Keep container tightly closed. P260: Do not breathe . P261: Avoid breathing P264: Wash hands thoroughly after handling. P270: Do not eat, drink or smoke when using this product. P271: Use only outdoors or in a well-ventilated area. P280: Wear . P301 + P312: IF SWALLOWED: Call a POISON CENTER or doctor/physician if you feel unwell. P302 + P352: IF ON SKIN: Wash with plenty of soap and water. P304: IF INHALED: . P304 + P340: IF INHALED: Remove victim to fresh air and keep at rest in a position comfortable for breathing. P305 + P351 + P338: IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. P312: Call a POISON CENTER or doctor/physician if you feel unwell. P321: Specific treatment (see . on this label). P330: Rinse mouth. P332 + P313: If skin irritation occurs: Get medical advice/ attention. P337 + P313: If eye irritation persists: Get medical advice/attention. P340: Remove victim to fresh air and keep at rest in a position comfortable for breathing. P362: Take off contaminated clothing and wash before reuse. P403: Store in a well-ventilated place. P403 + P233: Store in a well-ventilated place. Keep container tightly closed. P405: Store locked up. P501: Dispose of contents/container to local regulations.

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