(2R,3S,10R,11R)-silybin | 891827-72-8

• 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: (2R,3S,10R,11R)-silybin
• 英文别名: 2,3-cis-silybin A；(2R,3S)-3,5,7-trihydroxy-2-[(2R,3R)-3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]-2,3-dihydrochromen-4-one
• CAS: 891827-72-8
• 化学式: C₂₅H₂₂O₁₀
• 分子量: 482.444
• InChiKey: SEBFKMXJBCUCAI-KMRPREKFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.36
• 重原子数：
  35.0
• 可旋转键数：
  4.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  155.14
• 氢给体数：
  5.0
• 氢受体数：
  10.0

反应信息

• 作为产物：
  描述：

  水飞蓟宾 在 三氟化硼乙醚 作用下， 以 乙醚 、 甲基叔丁基醚 、 N,N-二甲基甲酰胺 、 正丁醇 为溶剂， 反应 149.0h， 生成 (2R,3S,10R,11R)-silybin
  参考文献：
  名称：

  cis–trans Isomerization of silybins A and B

  摘要：

  方法已经开发和优化，用Lewis酸催化（BF₃∙OEt₂）对硅基素丙素A (1a)和B (1b)（顺式异构体）进行异构化，制备2,3-cis和10,11-cis异构体。所有光学纯化合物的绝对构型通过使用NMR和将它们的电子圆二色性数据与已知绝对构型的模型化合物进行比较来确定。提出了硅基素丙素cis–trans异构化的机理，并得到了量子力学计算的支持。

  DOI：

  10.3762/bjoc.10.105

文献信息

• Compositions containing silymarin and sulfoalkyl ether cyclodextrin and methods of using the same
  申请人：UNIVERSITY OF KANSAS

  公开号：US10702568B2

  公开（公告）日：2020-07-07

  Cosmetic and dietary supplement compositions containing silymarin and sulfoalkyl ether cyclodextrin, particularly sulfobutyl ether cyclodextrin, are described. The compositions and methods are useful in reducing appearance of facial redness in rosacea-prone skin, rejuvenating skin, preventing skin aging, inhibiting oxidative stress in epidermal and dermal cells, increasing collagen production, reducing the likelihood of skin cancer, treating or reducing liver damage from a toxin, or treating a liver disease.

  描述了含有水飞蓟素和磺烷基醚环糊精，特别是磺丁基醚环糊精的化妆品和膳食补充剂组合物。这些组合物和方法可用于减少易患红斑痤疮的皮肤出现面部发红、嫩肤、防止皮肤老化、抑制表皮和真皮细胞中的氧化应激、增加胶原蛋白的生成、减少皮肤癌的可能性、治疗或减少毒素对肝脏的损害或治疗肝病。
• COMPOSITIONS CONTAINING SILYMARIN AND SULFOALKYL ETHER CYCLODEXTRIN AND METHODS OF USING THE SAME
  申请人：CyDex Pharmaceuticals, Inc.

  公开号：US20180133274A1

  公开（公告）日：2018-05-17

  Cosmetic and dietary supplement compositions containing silymarin and sulfoalkyl ether cyclodextrin, particularly sulfobutyl ether cyclodextrin, are described. The compositions and methods are useful in reducing appearance of facial redness in rosacea-prone skin, rejuvenating skin, preventing skin aging, inhibiting oxidative stress in epidermal and dermal cells, increasing collagen production, reducing the likelihood of skin cancer, treating or reducing liver damage from a toxin, or treating a liver disease.
• <i>cis</i>–<i>trans</i> Isomerization of silybins A and B
  作者：Michaela Novotná、Radek Gažák、David Biedermann、Florent Di Meo、Petr Marhol、Marek Kuzma、Lucie Bednárová、Kateřina Fuksová、Patrick Trouillas、Vladimír Křen

  DOI：10.3762/bjoc.10.105

  日期：——

  Methods were developed and optimized for the preparation of the 2,3-cis- and the 10,11-cis-isomers of silybin by the Lewis acid catalyzed (BF₃∙OEt₂) isomerization of silybins A (1a) and B (1b) (trans-isomers). The absolute configuration of all optically pure compounds was determined by using NMR and comparing their electronic circular dichroism data with model compounds of known absolute configurations. Mechanisms for cis–trans-isomerization of silybin are proposed and supported by quantum mechanical calculations.

  方法已经开发和优化，用Lewis酸催化（BF₃∙OEt₂）对硅基素丙素A (1a)和B (1b)（顺式异构体）进行异构化，制备2,3-cis和10,11-cis异构体。所有光学纯化合物的绝对构型通过使用NMR和将它们的电子圆二色性数据与已知绝对构型的模型化合物进行比较来确定。提出了硅基素丙素cis–trans异构化的机理，并得到了量子力学计算的支持。