22β-acetoxy-3β,24-isopropylidenedioxyolean-12-ene | 83689-21-8

• 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-acetoxy-3β,24-isopropylidenedioxyolean-12-ene
• 英文别名: [(1R,2R,5S,10S,11R,14R,15S,18R,19R,23S)-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] acetate
• CAS: 83689-21-8
• 化学式: C₃₅H₅₆O₄
• 分子量: 540.827
• InChiKey: IYXFFBVZJSSJEZ-FOLPGSSQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.48
• 重原子数：
  39.0
• 可旋转键数：
  1.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  44.76
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  22β-acetoxy-3β,24-isopropylidenedioxyolean-12-ene 在 甲醇 、 三氟化硼乙醚 、 sodium methylate 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 11.08h， 生成 3,24-di-O-methylsoyasapogenol B
  参考文献：
  名称：

  Kitagawa, Isao; Wang, Hui Kang; Taniyama, Toshio, Chemical and pharmaceutical bulletin, 1988, vol. 36, # 1, p. 153 - 161

  摘要：

  DOI：
• 作为产物：
  描述：

  大豆甾醇 B 在 吡啶 、 Dowex 50Wx8 作用下， 以 丙酮 为溶剂， 反应 24.0h， 生成 22β-acetoxy-3β,24-isopropylidenedioxyolean-12-ene
  参考文献：
  名称：

  Kitagawa, Isao; Wang, Hui Kang; Taniyama, Toshio, Chemical and pharmaceutical bulletin, 1988, vol. 36, # 1, p. 153 - 161

  摘要：

  DOI：

文献信息

• Preventive effects of soyasapogenol B derivatives on liver injury in a concanavalin A-induced hepatitis model
  作者：Kazue Sasaki、Nobuto Minowa、Hiroyuki Kuzuhara、Shoji Nishiyama

  DOI：10.1016/j.bmc.2005.04.074

  日期：2005.8

  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.
• Synthesis and hepatoprotective effects of soyasapogenol B derivatives
  作者：Kazue Sasaki、Nobuto Minowa、Hiroyuki Kuzuhara、Shoji Nishiyama、Shoji Omoto

  DOI：10.1016/s0960-894x(96)00572-0

  日期：1997.1

  Derivatives of soyasapogenol B (1), which is the aglycon moiety of soyasaponins from soybean, were synthesized and evaluated for their hepatoprotective effects in vitro. Copyright (C) 1996 Elsevier Science Ltd