cimicifugoside H-3 | 163046-74-0

• 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: cimicifugoside H-3
• 英文别名: (1S,3R,6S,8R,12R,15R,16R,18S)-18-hydroxy-15-[(2R)-5-hydroxy-4-oxopentan-2-yl]-7,7,12,16-tetramethyl-6-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxypentacyclo[9.7.0.01,3.03,8.012,16]octadec-10-en-14-one
• CAS: 163046-74-0
• 化学式: C₃₂H₄₈O₉
• 分子量: 576.728
• InChiKey: QMZIBXOWLZVKEF-JCAQTXDJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  41
• 可旋转键数：
  6
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  154
• 氢给体数：
  5
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  cimicifugoside H-3 在 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 168.0h， 生成 (3S,5R,9S,10R,11S,13R,14R,17R)-3,11-Dihydroxy-17-((R)-4-hydroxy-1-methyl-3-oxo-butyl)-4,4,13,14-tetramethyl-2,3,5,6,11,12,13,14,15,17-decahydro-1H,4H-cyclopropa[9,10]cyclopenta[a]phenanthren-16-one
  参考文献：
  名称：

  Studies on the Chinese Crude Drug "Shoma". X. Three New Trinor-9,19-cyclolanostanol Xylosides, Cimicifugosides H-3, H-4 and H-6, from Cimicifuga Rhizome and Transformation of Cimicifugoside H-1 into Cimicifugosides H-2, H-3 and H-4.

  摘要：

  Three trinor-triterpenol glycosides were isolated from a batch of commercial Cimicifuga Rhizome : cimicifugoside H-3 (1), C32H48O9, mp 249-251 °C, [α]D -22.3°, cimicifugoside H-4 (2), C32H48O9, mp 265-267 °C, [α]D -75.0°, and cimicifugoside H-6 (3), C32H<48>O10, mp 275-276 °C, [α]D -64.3°, On the basis of chemical and spectral data, the structure of 1 was proposed to be 11β, 24-dihydroxy-3β-(β-D-xylopyranosyloxy)-25, 26, 27-trinor-9, 19-cyclolanost-7-ene-16, 23-dione. Cimicifugoside H-4 (2), 11β, 16α, 24α-trihydroxy-3β-(β-D-xylopyranosyloxy)-25, 26, 27-trinor-9, 19 : 16, 24-dicyclolanost-7-en-23-one, seems to be generated from intramolecular aldol condensation between C-16 and C-24 of 1. Cimicifugoside H-6 (3) is the 15α-hydroxy derivative of 2. Cimicifugoside H-2 (5), which has already been obtained from cimicifugoside H-1 (4) under an acidic condition, was found to give 1, 2 and an α-hydroxy enone (2a) under an alkaline condition.

  DOI：

  10.1248/cpb.43.1475
• 作为产物：
  描述：

  升麻素苷H-2 在 碳酸氢钠 作用下， 以 甲醇 为溶剂， 反应 4.0h， 生成 cimicifugoside H-3 、 cimicifugoside H-4
  参考文献：
  名称：

  Studies on the Chinese Crude Drug "Shoma". X. Three New Trinor-9,19-cyclolanostanol Xylosides, Cimicifugosides H-3, H-4 and H-6, from Cimicifuga Rhizome and Transformation of Cimicifugoside H-1 into Cimicifugosides H-2, H-3 and H-4.

  摘要：

  Three trinor-triterpenol glycosides were isolated from a batch of commercial Cimicifuga Rhizome : cimicifugoside H-3 (1), C32H48O9, mp 249-251 °C, [α]D -22.3°, cimicifugoside H-4 (2), C32H48O9, mp 265-267 °C, [α]D -75.0°, and cimicifugoside H-6 (3), C32H<48>O10, mp 275-276 °C, [α]D -64.3°, On the basis of chemical and spectral data, the structure of 1 was proposed to be 11β, 24-dihydroxy-3β-(β-D-xylopyranosyloxy)-25, 26, 27-trinor-9, 19-cyclolanost-7-ene-16, 23-dione. Cimicifugoside H-4 (2), 11β, 16α, 24α-trihydroxy-3β-(β-D-xylopyranosyloxy)-25, 26, 27-trinor-9, 19 : 16, 24-dicyclolanost-7-en-23-one, seems to be generated from intramolecular aldol condensation between C-16 and C-24 of 1. Cimicifugoside H-6 (3) is the 15α-hydroxy derivative of 2. Cimicifugoside H-2 (5), which has already been obtained from cimicifugoside H-1 (4) under an acidic condition, was found to give 1, 2 and an α-hydroxy enone (2a) under an alkaline condition.

  DOI：

  10.1248/cpb.43.1475