三甲胺N-氧化物

生物活性靶点体外研究体内研究三甲胺N-氧化物试剂级价格

三甲胺N-氧化物

CAS号:1184-78-7
英文名:Trimethylamine N-oxide
中文名:三甲胺N-氧化物
CBNumber:CB6140124
分子式:C3H9NO
分子量:75.11
MOL File:1184-78-7.mol

三甲胺N-氧化物化学性质

熔点 :220-222 °C (lit.)
沸点 :133.8°C (rough estimate)
密度 :0.9301 (rough estimate)
蒸气压 :23.5Pa at 20℃
折射率 :1.4698 (estimate)
FEMA :4245 | TRIMETHYLAMINE OXIDE
储存条件 :Hygroscopic, Room Temperature, under inert atmosphere
溶解度 :Chloroform, DMSO, Methanol (Slightly)
酸度系数(pKa) :4.65(at 25℃)
形态 :Solid
颜色 :Pale Yellow
气味 (Odor) :odorless
水溶解性 :793g/L at 24.5℃
Merck :14,9711
JECFA Number :1614
稳定性 :Hygroscopic
LogP :-2.79
EPA化学物质信息 :Methanamine, N,N-dimethyl-, N-oxide (1184-78-7)

安全信息

危险品标志 :Xi
危险类别码 :36/37/38
安全说明 :26-37/39
WGK Germany :3
海关编码 :2904.20.5000

三甲胺N-氧化物性质、用途与生产工艺

生物活性 Trimethylamine N-oxide 是一种膳食胆碱和其他含三甲胺营养素的肠道微生物依赖性代谢产物。Trimethylamine N-oxide 通过激活 ROS/NLRP3 炎性体诱导炎症。Trimethylamine N-oxide 还通过激活 TGF-β/smad2 信号通路来加速成纤维细胞的分化并诱导心脏纤维化。
靶点

ROS/NLRP3 inflammasome
TGF-β/smad2
体外研究

The size and migration of fibroblasts are increased after Trimethylamine N-oxide (TMAO) treatment compared with non-treated fibroblasts in vitro. Trimethylamine N-oxide increases TGF-β receptor I expression, which promotes the phosphorylation of Smad2 and up-regulates the expression of α-SMA and collagen I. The ubiquitination of TGF-βRI is decreased in neonatal mouse fibroblasts after Trimethylamine N-oxide treatment. Trimethylamine N-oxide also inhibits the expression of smurf2.
Trimethylamine N-oxide is frequently found in the tissues of a variety of marine organisms that protects against the adverse effects of temperature, salinity, high urea and hydrostatic pressure.
体内研究

Trimethylamine N-oxide (TMAO) contributes to cardiovascular diseases by promoting inflammatory responses. C57BL/6 mice are fed a normal diet, high-choline diet and/or 3-dimethyl-1-butanol (DMB) diet. The levels of Trimethylamine N-oxide and choline are increased in choline-fed mice. Left ventricular hypertrophy, pulmonary congestion, and diastolic dysfunction are markedly exacerbated in heart failure with preserved ejection fraction (HFpEF) mice fed high-choline diets compared with mice fed the control diet. Myocardial fibrosis and inflammation were markedly increased in HFpEF mice fed high-choline diets compared with animals fed the control diet.
生产方法

将100ml三甲胺水溶液与600ml过氧化氢溶液相混合，在室温放置24h后，如果还有胺的气味，就再加100～200ml的过氧化氢溶液，当所有胺均被氧化后，在减压下蒸发至干。残余物用乙醇-乙醚混合物重结晶。得二水合氧化三甲胺，为长针状晶体，产率95%。

在油浴中减压至1.33～1.6kpa并加热到120℃，慢慢地升温至150℃，当水分被驱除后，升温至180℃～200℃，纯的无水氧化三甲胺即升华在瓶子较冷的颈部。

另一种脱水法：将45.0g二水合氧化三甲胺溶于300ml热DMF中，盛于圆底烧瓶中进行蒸馏。先在常压下加热以蒸去溶剂，直到沸点达到152～153℃。然后用水泵减压以除去残留的溶剂。蒸馏的末了将油浴的温度慢慢地升至120℃。剩下的无水氧化三甲胺重30g.