4,17(20)-pregnadiene-3-one-16β-ol | 85769-67-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: 4,17(20)-pregnadiene-3-one-16β-ol
• 英文别名: Z-guggulsterol；16beta-Hydroxy-4,17(20)z-pregnadien-3-one；(8R,9S,10R,13S,14S,16S,17Z)-17-ethylidene-16-hydroxy-10,13-dimethyl-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-3-one
• CAS: 85769-67-1
• 化学式: C₂₁H₃₀O₂
• 分子量: 314.468
• InChiKey: YCFSRIUWADDJEY-YWBGOIJPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  23
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4,17(20)-pregnadiene-3-one-16β-ol 在 吡啶 、 氯磺酸 、 sodium hydroxide 作用下， 以 氯仿 、 甲醇 、 水 为溶剂， 反应 4.5h， 以34.3%的产率得到4,17(20)-pregnadiene-3-one-16β-sulfate sodium salt
  参考文献：
  名称：

  Guggullipid derivatives: synthesis and applications

  摘要：

  Two guggullipid derivatives,Z-guggulsulfate [4,17(20)-pregnadiene-3-one-16 beta-sulfate] sodium salt and Z-guggullaurate (4,17(20)-pregnadiene-3-one-16 beta-laurate], have been synthesized and evaluated for liposomal drug delivery system. Its precursor, Z-guggulsterol [4,17(20)-pregnadiene-3-one-16 beta-ol], is also synthesized in gram scale starting from guggulsterone using the novel combination of known reactions in fewer steps and with higher yield than previously reported synthesis. These new synthetic guggullipid derivatives were also used in the preparation of liposomes. This new class of lipid molecules will be a useful tool in the development of nanosomal or liposomal drug delivery system. (C) 2010 Elsevier Ireland Ltd. All rights reserved.

  DOI：

  10.1016/j.chemphyslip.2010.02.004
• 作为产物：
  描述：

  4,17(20)-pregnadiene-3,16-diol 在 manganese(IV) oxide 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以7.56 g的产率得到4,17(20)-pregnadiene-3-one-16β-ol
  参考文献：
  名称：

  Guggullipid derivatives: synthesis and applications

  摘要：

  Two guggullipid derivatives,Z-guggulsulfate [4,17(20)-pregnadiene-3-one-16 beta-sulfate] sodium salt and Z-guggullaurate (4,17(20)-pregnadiene-3-one-16 beta-laurate], have been synthesized and evaluated for liposomal drug delivery system. Its precursor, Z-guggulsterol [4,17(20)-pregnadiene-3-one-16 beta-ol], is also synthesized in gram scale starting from guggulsterone using the novel combination of known reactions in fewer steps and with higher yield than previously reported synthesis. These new synthetic guggullipid derivatives were also used in the preparation of liposomes. This new class of lipid molecules will be a useful tool in the development of nanosomal or liposomal drug delivery system. (C) 2010 Elsevier Ireland Ltd. All rights reserved.

  DOI：

  10.1016/j.chemphyslip.2010.02.004

文献信息

• Guggullipid derivatives: synthesis and applications
  作者：Moghis U. Ahmad、Shoukath M. Ali、Ateeq Ahmad、Saifuddin Sheikh、Imran Ahmad

  DOI：10.1016/j.chemphyslip.2010.02.004

  日期：2010.5

  Two guggullipid derivatives,Z-guggulsulfate [4,17(20)-pregnadiene-3-one-16 beta-sulfate] sodium salt and Z-guggullaurate (4,17(20)-pregnadiene-3-one-16 beta-laurate], have been synthesized and evaluated for liposomal drug delivery system. Its precursor, Z-guggulsterol [4,17(20)-pregnadiene-3-one-16 beta-ol], is also synthesized in gram scale starting from guggulsterone using the novel combination of known reactions in fewer steps and with higher yield than previously reported synthesis. These new synthetic guggullipid derivatives were also used in the preparation of liposomes. This new class of lipid molecules will be a useful tool in the development of nanosomal or liposomal drug delivery system. (C) 2010 Elsevier Ireland Ltd. All rights reserved.