diosgenin monoitaconate | 1044508-17-9

• 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: diosgenin monoitaconate
• 英文别名: 2-methylidene-4-oxo-4-[(1S,2S,4S,5'R,6R,7S,8R,9S,12S,13R,16S)-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icos-18-ene-6,2'-oxane]-16-yl]oxybutanoic acid
• CAS: 1044508-17-9
• 化学式: C₃₂H₄₆O₆
• 分子量: 526.714
• InChiKey: OGZJYVDEINAEJY-WZPWMEOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  38
• 可旋转键数：
  5
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  82.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  diosgenin monoitaconate 在 氯化亚砜 作用下， 反应 0.5h， 生成
  参考文献：
  名称：

  Novel drug delivery systems: Chitosan conjugates covalently attached to steroids with potential anticancer and agrochemical activity

  摘要：

  Chitosan (CS) was linked to diosgenin monoesters with potential anticancer and agrochemical activity employing several methods (i.e. solid phase microwave assisted synthesis with carbodiimides activation, acyl chloride approach and homogeneous reaction with carbodiimides activation in aqueous solution). The steroid contents found by elemental analysis were between 5 and 33% (w/w) and was dependent on the nature of the employed linker and the steroid-CS conjugates preparation method. Linking was confirmed by FTIR spectroscopy. Differential scanning calorimetry studies are presented. In vitro release studies performed in water at different pH indicated a drug release dependence on the dicarboxylic acid employed as linker, the steroid content and the acidity of the solution. The obtained conjugates can be potentially applied as films, microspheres or gels for delivery of plant growth regulators in agriculture and anticancer drugs. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carbpol.2010.12.007
• 作为产物：
  描述：

  衣康酸酐 、 薯蓣皂素 生成 diosgenin monoitaconate
  参考文献：
  名称：

  Novel drug delivery systems: Chitosan conjugates covalently attached to steroids with potential anticancer and agrochemical activity

  摘要：

  Chitosan (CS) was linked to diosgenin monoesters with potential anticancer and agrochemical activity employing several methods (i.e. solid phase microwave assisted synthesis with carbodiimides activation, acyl chloride approach and homogeneous reaction with carbodiimides activation in aqueous solution). The steroid contents found by elemental analysis were between 5 and 33% (w/w) and was dependent on the nature of the employed linker and the steroid-CS conjugates preparation method. Linking was confirmed by FTIR spectroscopy. Differential scanning calorimetry studies are presented. In vitro release studies performed in water at different pH indicated a drug release dependence on the dicarboxylic acid employed as linker, the steroid content and the acidity of the solution. The obtained conjugates can be potentially applied as films, microspheres or gels for delivery of plant growth regulators in agriculture and anticancer drugs. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carbpol.2010.12.007

文献信息

• Microwave Assisted Synthesis of Diosgenin Esters of Maleic and Itaconic Acids
  作者：Ariel Martínez-García、Ricardo Martínez

  DOI：10.1080/00397910801997520

  日期：2008.5.23

  Diosgenin monomaleate and diosgenin monoitaconate were prepared by the esterification of diosgenin with maleic and itaconic anhydride, respectively, in toluene using p-toluenesulphonic acid as catalyst. A domestic microwave oven was modified and used for the synthesis of both products. The reaction time for consuming all the diosgenin according to thin-layer chromatography (TLC) was reduced by around 90% in the synthesis of monomaleate of diosgenin as well as in the synthesis of monoitaconate of diosgenin in comparison with conventional heating, whereas the monomaleate of diosgenin yield increased from 43 to 80-85% and the monoitaconate of diosgenin yield from 34 to 95% under the same experimental conditions. It was easier to purify the diosgenin monoitaconate than the diosgenin monomaleate. Both products were characterized by NMR and FTIR spectroscopy.