22β-hydroxymethyl-3β,24-isopropilidenedioxyolean-12-ene | 187393-88-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 22β-hydroxymethyl-3β,24-isopropilidenedioxyolean-12-ene
• 英文别名: [(1R,2R,5S,10S,11R,14R,15S,18R,19R,23R)-2,7,7,10,14,15,18,21,21-nonamethyl-6,8-dioxahexacyclo[12.12.0.02,11.05,10.015,24.018,23]hexacos-24-en-19-yl]methanol
• CAS: 187393-88-0
• 化学式: C₃₄H₅₆O₃
• 分子量: 512.817
• InChiKey: IGPKFQPHIKKJHS-RCVZRCNYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.16
• 重原子数：
  37.0
• 可旋转键数：
  1.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  38.69
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  22β-hydroxymethyl-3β,24-isopropilidenedioxyolean-12-ene 在 sodium chlorite 、 sodium dihydrogenphosphate 、 2-甲基-2-丁烯 、 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 二氯甲烷 、 水 、 叔丁醇 为溶剂， 生成 3β,24-isopropilidenedioxyolean-12-ene-22β-carboxylic acid
  参考文献：
  名称：

  Preventive effects of soyasapogenol B derivatives on liver injury in a concanavalin A-induced hepatitis model

  摘要：

  To shed light on the structure-activity relationship, various so soyasapogenol B derivatives were synthesized and evaluated for preventive effects on liver injury in the concanavalin A (Con A)-induced hepatitis model in mice, Con A injection into mice induces some pathophysiology of human liver disease such as autoimmune or viral hepatitis, Two hydroxyl groups on the A ring of soyasapogenol B are required for amelioration of liver damage, Modification of the C-22 hydroxyl moiety with an acyloxy or alkyloxy group, or removal of the hydroxyl group. resulted in I greatly enhanced percentage of alleviation. Among the series of soyasapogenol B derivatives examined, six compounds exhibited preventive effects on liver damage. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.04.074
• 作为产物：
  描述：

  22β-hydroxy-3β,24-isopropylidenedioxyolean-12-ene 在 盐酸 、 硼烷四氢呋喃络合物 、 camphor-10-sulfonic acid 、 四氯化钛 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 丙酮 为溶剂， 反应 42.25h， 生成 22β-hydroxymethyl-3β,24-isopropilidenedioxyolean-12-ene
  参考文献：
  名称：

  Preventive effects of soyasapogenol B derivatives on liver injury in a concanavalin A-induced hepatitis model

  摘要：

  To shed light on the structure-activity relationship, various so soyasapogenol B derivatives were synthesized and evaluated for preventive effects on liver injury in the concanavalin A (Con A)-induced hepatitis model in mice, Con A injection into mice induces some pathophysiology of human liver disease such as autoimmune or viral hepatitis, Two hydroxyl groups on the A ring of soyasapogenol B are required for amelioration of liver damage, Modification of the C-22 hydroxyl moiety with an acyloxy or alkyloxy group, or removal of the hydroxyl group. resulted in I greatly enhanced percentage of alleviation. Among the series of soyasapogenol B derivatives examined, six compounds exhibited preventive effects on liver damage. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.04.074

文献信息

• Efficient synthesis of C(22) homologous derivatives of hepatoprotective soyasapogenol B
  作者：Kazue Sasaki、Nobuto Minowa、Hiroyuki Kuzuhara、Shoji Nishiyama、Shoji Omoto

  DOI：10.1016/s0040-4039(97)10256-8

  日期：1997.12

  Stereochemical behavior in the addition reactions at C(22) of ketone 5 and exomethylene 6 was studied and C(22) homologous derivatives of soyasapogenol B were efficiently synthesized (C) 1997 Elsevier Science Ltd.