(S)-20-Protopanaxatriol | 1453-93-6

• 物质功能分类: 生物化工 - 中草药成分
• 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: (S)-20-Protopanaxatriol
• 英文别名: 20(S)-Protopanaxatriol；Panaxatriol；(3S,6S,8R,10R,12R,14R,17S)-17-[(2S)-2-hydroxy-6-methylhept-5-en-2-yl]-4,4,8,10,14-pentamethyl-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-3,6,12-triol
• CAS: 1453-93-6；34080-08-5
• 化学式: C₃₀H₅₂O₄
• 分子量: 476.74
• InChiKey: SHCBCKBYTHZQGZ-HXWXQLNHSA-N

物化性质

• 熔点：
  261-263 °C
• 沸点：
  590.0±50.0 °C(Predicted)
• 密度：
  1.079±0.06 g/cm3(Predicted)
• 溶解度：
  DMSO：≥32mg/mL（67.12mM）；

计算性质

• 辛醇/水分配系数(LogP)：
  5.47
• 重原子数：
  34.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  80.92
• 氢给体数：
  4.0
• 氢受体数：
  4.0

安全信息

• 储存条件：
  2-8°C

制备方法与用途

用途　(20R)-原人参三醇是一种甾体苷衍生物，具有抑制或阻止癌细胞生长的活性。

反应信息

• 作为产物：
  描述：

  Ginsenosides Rg1 在 sodium hydroxide 作用下， 以 正丁醇 为溶剂， 反应 15.0h， 生成 (S)-20-Protopanaxatriol 、 sodium formate
  参考文献：
  名称：

  Novel Mechanism for Oxidative Cleavage of Glycosidic Bonds: Evidence for an Oxygen Dependent Reaction

  摘要：

  In a previous work from our laboratory, an optimized procedure was worked out for cleavage of the glucosidic bonds in ginsenosides (Cui, J. F.; Garle, M.; Lund, E.; Bjorkhem, I.; Eneroth, P. Anal. Biochem. 1993, 210, 411-417). When the reaction was performed in n-butanol, alkaline conditions were found to give a considerably better and almost quantitative yield of intact aglyconic-specific products than did acidic conditions. This is surprising in view of the current concept that glucosidic bonds are more stable under alkaline than acidic conditions. It is shown here that the alkaline cleavage is oxygen dependent and that there is little or no conversion when oxygen or air is replaced with nitrogen. Addition of an anti-oxidant, glucose or water also reduces the degree of cleavage under the conditions employed. Replacement of n-butanol for sec-, iso- or 2-methyl-2-propanol, decreased the yield of products to about 75% and when n- or isopropanol was used as solvent the yield decreased to about 40%. It was shown that the glucose moiety was completely degraded under the conditions employed and that formate and carbonate, in a ratio of 5/1, were the major products. A mechanistic rationale for the oxygen dependent cleavage of the glucosidic bonds is suggested. The possibility that this mechanism may be of protective importance in biological systems under some specific conditions is also discussed.

  DOI：

  10.1021/jo00105a050

文献信息

• Novel Mechanism for Oxidative Cleavage of Glycosidic Bonds: Evidence for an Oxygen Dependent Reaction
  作者：Jian-Fang Cui、Styrbjoern Bystroem、Peter Eneroth、Ingemar Bjoerkhem

  DOI：10.1021/jo00105a050

  日期：1994.12

  In a previous work from our laboratory, an optimized procedure was worked out for cleavage of the glucosidic bonds in ginsenosides (Cui, J. F.; Garle, M.; Lund, E.; Bjorkhem, I.; Eneroth, P. Anal. Biochem. 1993, 210, 411-417). When the reaction was performed in n-butanol, alkaline conditions were found to give a considerably better and almost quantitative yield of intact aglyconic-specific products than did acidic conditions. This is surprising in view of the current concept that glucosidic bonds are more stable under alkaline than acidic conditions. It is shown here that the alkaline cleavage is oxygen dependent and that there is little or no conversion when oxygen or air is replaced with nitrogen. Addition of an anti-oxidant, glucose or water also reduces the degree of cleavage under the conditions employed. Replacement of n-butanol for sec-, iso- or 2-methyl-2-propanol, decreased the yield of products to about 75% and when n- or isopropanol was used as solvent the yield decreased to about 40%. It was shown that the glucose moiety was completely degraded under the conditions employed and that formate and carbonate, in a ratio of 5/1, were the major products. A mechanistic rationale for the oxygen dependent cleavage of the glucosidic bonds is suggested. The possibility that this mechanism may be of protective importance in biological systems under some specific conditions is also discussed.