CAS: 802918-57-6; (2R,3R)-3,5,7-Trihydroxy-2-(3-(4-Hydroxy-3-Methoxyphenyl)-2-(Hydroxymethyl)-2,3-Dihydrobenzo[b][1,4]Dioxin-6-yl)Chroman-4-One

该化合物是来自乳液本植物(Silybum marianum)的氟氯素化合物,主要因其肝脏保护特性而得到承认,成为肝脏健康的流行补充物;Silybin表现出抗氧化剂活动,有助于中和自由基和减少细胞中的氧化性压力;该化合物已知与各种细胞路径相互作用,有可能影响炎症和细胞信号;Silybin经常在肝脏肝炎,肝炎,甚至某些癌症等条件下被研究其潜在的治疗影响;通常以硅质素的形式提供,这是包括硅素在内的一种复合物,其主要活性成分;在溶液方面,硅碱在水中相对不易溶,但可以通过各种配方增强.其安全性特征一般是有利的,尽管有些人可能经历胃肠紊乱.

英文名称(2R,3R)-3,5,7-Trihydroxy-2-(3-(4-Hydroxy-3-Methoxyphenyl)-2-(Hydroxymethyl)-2,3-Dihydrobenzo[b][1,4]Dioxin-6-yl)Chroman-4-One
中文名称水飞蓟素A,B
IUPAC名称(2R,3R)-3,5,7-trihydroxy-2-(3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-2,3-dihydrobenzo[b][1,4]dioxin-6-yl)chroman-4-one
其它别名Silybin A,B (Mixture); Silybin (Mixture Of Diastereomers); 4H-1-Benzopyran-4-One, 2-[2,3-Dihydro-3-(4-Hydroxy-3-Methoxyphenyl)-2-(Hydroxymethyl)-1,4-Benzodioxin-6-Yl]-2,3-Dihydro-3,5,7-Trihydroxy-, (2R,3R)-; (2R,3R)-3,5,7-Trihydroxy-2-(3-(4-Hydroxy-3-Methoxyphenyl)-2-(Hydroxymethyl)-2,3-Dihydrobenzo[b][1,4]Dioxin-6-yl)Chroman-4-One; (2R,3R)-3,5,7-Trihydroxy-2-[3-(4-Hydroxy-3-Methoxyphenyl)-2-(Hydroxymethyl)-2,3-Dihydro-1,4-Benzodioxin-6-Yl]-2,3-Dihydrochromen-4-O Ne
CAS编号802918-57-6
MFCD编号:MFCD00872186
EINECS号:806-403-5
分子式:C25H22O10分子量:482.44
产品CID: 1798218
产品分类分析化学 → 分析试剂 → 离子色谱试剂

相似结构搜索
InChIKey: SEBFKMXJBCUCAI-DBMPWETRSA-N
InChI=1S/C25H22O10/c1-32-17-6-11(2-4-14(17)28)24-20(10-26)33-16-5-3-12(7-18(16)34-24)25-23(31)22(30)21-15(29)8-13(27)9-19(21)35-25/h2-9,20,23-29,31H,10H2,1H3/t20?,23-,24?
计算化学: 氢键受体数10.0氢键供体数5.0可旋转键数4.0

物理性质

熔点152-153°C
沸点793.0±60.0 °C(预测)
密度1.527±0.06 g/cm3(预测)
pKa:7.39±0.60(预测)
PSA:155.14
LogP:2.3627
溶解性Acetone (Sparingly, Sonicated, Heated), DMSO (Slightly), Methanol (Slightly, Heated)
外观形态淡黄色至米色固体
储存条件冰箱

MSDS等安全信息

GHS象形图
GHS符号GHS07;
注释: Exclamation mark
危险类别特定目标器官毒性 - 单次接触类别3
皮肤腐蚀/刺激类别2
严重眼刺激类别2
急性毒性类别4(经口)
警示词Warning(警告)
危险描述H335 |可能引起呼吸道刺激.
H315 |造成皮肤刺激.
H319 |造成严重眼刺激.
H302 |吞咽有害.
防范说明P264-P270-P301+P312+P330-P501
危险品标志Xi
安全声明26-37/39
危险类别码36/37/38
WGK Germany3

欧盟法规

C&L通报

上下游产品

23-O-butyrylsilybin 23-O-°CtanoylsilybinDehydrosilybin 2-(2-{[(tert-butyldimethylsilyl)oxy]methyl}-3-(4-hydroxy-3-methoxyphenyl)-2,3-dihydro-1,4-benzodioxin-6-yl)-3,5,7-trihydroxychroman-4-one 3,5,7-triacetoxy-2-[3-(4-acetoxy-3-methoxyphenyl)-2-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]chroman-4-one

合成工艺路线路线简述

📜23-O-octanoylsilybin置于candida Antarctica Lipase B,正丁醇体系中,用甲基叔丁基醚作为反应溶剂,化学反应 29.0H,反应生成水飞蓟素a,B
参考文献:Enzymatic Kinetic Resolution Of Silybin Diastereoisomers
标题:Enzymatic Kinetic Resolution Of Silybin Diastereoisomers
摘要:In Nature,The Flavonolignan Silybin (1) occurs As A Mixture Of Two Diastereomers,Silybin A And Silybin B,Which In A Number Of Biological Assays Exhibit Different Activities. A Library Of Hydrolases (Lipases,Esterases,And Proteases) Was Tested For Separating The Silybin A And B Diastereomers By Selective Transcsterification Or By Stereoselective Alcoholysis Of 23-O-Acetylsilybin (2). Novozym 435 Proved To Be The Most Suitable Enzyme For The Preparative Production Of Both Optically Pure Silybins A And B By Enzymatic Discrimination. Gram Amounts Of The Optically Pure Substances Can Be Produced Within One Week,And The New Method Is Robust And Readily Scalable To Tens Of Grams.
DOI:10.1021/np900758D