3,5,7,20-tetra-O-acetylsilybin | 802918-29-2

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 黄酮木脂素
• 英文名称: 3,5,7,20-tetra-O-acetylsilybin
• 英文别名: 3,5,7-triacetoxy-2-[3-(4-acetoxy-3-methoxyphenyl)-2-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]chroman-4-one；3,5,7,20-O-tetra-acetyl-silybin
• CAS: 802918-29-2
• 化学式: C₃₃H₃₀O₁₄
• 分子量: 650.593
• InChiKey: IALHFROZCIWNOA-DOIWODGYSA-N

物化性质

• 沸点：
  780.9±60.0 °C(Predicted)
• 密度：
  1.46±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.59
• 重原子数：
  47.0
• 可旋转键数：
  8.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  179.42
• 氢给体数：
  1.0
• 氢受体数：
  14.0

反应信息

• 作为反应物：
  描述：

  3,5,7,20-tetra-O-acetylsilybin 在 chromium(VI) oxide 、 potassium carbonate 、 高碘酸 作用下， 以 甲醇 、 水 、 乙腈 为溶剂， 反应 24.75h， 生成 3-(4-hydroxy-3-methoxyphenyl)-6-(3,5,7-trihydroxy-4-oxochroman-2-yl)-2,3-dihydro-1,4-benzodioxine-2-carboxylic acid
  参考文献：
  名称：

  Oxidised derivatives of silybin and their antiradical and antioxidant activity

  摘要：

  Carboxylic acids derived from silybin (1) and 2,3-dehydrosilybin (2) with improved water solubility were prepared by selective oxidation of parent compounds and a new inexpensive method for preparation of 2,3-dehydrosilybin from silybin was developed and optimised. The antioxidative properties of the above-mentioned compounds and of side product 3a from oxidation of compound 1 were determined by cyclic voltammetry, free radical scavenging (DPPH, superoxide) assays, and by inhibition of in vitro generated liver microsomal lipid peroxidation. Dehydrogenation at C-(2)-C-(3) in flavonolignans (silybin vs 2,3-dehydrosilybin; silybinic acid vs 2,3-dehydrosilybinic acid) strongly improved antioxidative properties (analogously as in flavonoids taxifolin vs quercetin). Thus, in antioxidative properties, dehydrosilybin was superior to silybin by one order, but its water solubility is too low for application in aqueous milieu. On the other hand, 2,3-dehydrosilybinic acid is a fairly soluble derivative with antilipoperoxidation and antiradical activities better than that of silybin. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.07.064
• 作为产物：
  描述：

  水飞蓟素A,B 在 吡啶 、 甲酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 0.5h， 生成 3,5,7,20-tetra-O-acetylsilybin
  参考文献：
  名称：

  水飞蓟宾和2,3-脱氢水飞蓟宾的新型C-23改性：抗氧化性能的合成和初步评估

  摘要：

  水飞蓟宾是水飞蓟素的主要黄酮木脂素，它具有多种生物学效应，通常归因于其抗氧化性能。本文中，我们将描述一种有效的合成策略，以使用以下方法获得各种新的和更水溶性的水飞蓟宾和2,3-脱氢水飞蓟宾（DHS）衍生物，其中23-羟基被转化为硫酸盐，磷酸二酯或胺基解决方案阶段的方法。此外，开发和优化了一种新的，高效的从水飞蓟宾制备DHS的方法。 在体内细胞模型中评估了新化合物的抗氧化性能，它们显示出的抗氧化活性与水飞蓟宾和DHS相当或更高，能够防止H 2 O 2诱导的细胞内活性氧（ROS）生成。大多数衍生物还表现出更好的亲水性，同时保留了水飞蓟宾的生物活性，它们可能会拓宽此类天然化合物的体内应用范围。

  DOI：

  10.1016/j.bmcl.2011.06.049

文献信息

• New Silybin Scaffold for Chemical Diversification: Synthesis of Novel 23-Phosphodiester Silybin Conjugates
  作者：Giovanni Di Fabio、Armando Zarrelli、Valeria Romanucci、Marina Greca、Lorenzo De Napoli、Lucio Previtera

  DOI：10.1055/s-0032-1317688

  日期：——

  Silybin is the major component (ca. 30%) of the silymarin complex extracted from the seeds of Silybum marianum, with multiple biological activities operating at various cell levels. As an ongoing effort toward the exploitation of natural products as scaffolds for chemical diversification at readily accessible positions, we present here an efficient synthetic procedure to obtain new 23-phosphodiester silybin conjugates with different labels. A key point in our approach is the new 3,5,7,20-tetra-O-acetylsilybin-23-phosphoramidite, useful for a variety of derivatizations following a reliable and well-known chemistry. The feasibility of the procedure has been demonstrated by preparing new 23-silybin conjugates, exploiting standard phosphoramidite chemistry.