medicoside C | 102349-43-9

• 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: medicoside C
• 英文别名: 3-O-α-L-arabinopyranosyl(1→2)-β-D-glucopyranosyl(1→2)-α-L-arabinopyranosylhederagenin；3-O-[α-L-arabinopyranosyl(1->2)-β-D-glucopyranosyl(1->2)-α-L-arabinopyranosyl] hederagenin；(4aS,6aR,6aS,6bR,8aR,9R,10S,12aR,14bS)-10-[(2S,3R,4S,5S)-3-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]oxy-4,5-dihydroxyoxan-2-yl]oxy-9-(hydroxymethyl)-2,2,6a,6b,9,12a-hexamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid
• CAS: 102349-43-9
• 化学式: C₄₆H₇₄O₁₇
• 分子量: 899.083
• InChiKey: NMFXQSHZSKXLRM-JJYKKGDWSA-N

物化性质

• 沸点：
  996.6±65.0 °C(Predicted)
• 密度：
  1.41±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  63
• 可旋转键数：
  9
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  275
• 氢给体数：
  10
• 氢受体数：
  17

反应信息

• 作为反应物：
  描述：

  medicoside C 在 盐酸 作用下， 以 甲醇 、 水 为溶剂， 反应 8.0h， 生成 常春藤皂苷元
  参考文献：
  名称：

  紫花苜蓿皂苷酸水解过程中的人工制品形成。

  摘要：

  紫花苜蓿皂苷酸水解过程中获得的人工制品化合物。（豆科），已通过 GC-FID 进行监测和评估。它们的鉴定已通过 GC-MS 和 1H 和 13C NMR 进行。考虑了在三萜五环苷元上具有不同取代基的皂苷，并在 10 小时的时程反应中检测和量化了它们的水解产物。从大豆皂甙 B、C、D 和 F 中获得众所周知的大豆皂甙 B、C、D 和 F，以及先前未描述的皂甙人工制品，鉴定为 3β,22β,24-trihydroxyolean-18(19)-en 并命名为 soyasapogenol H。来自 zanhic acid saponin鉴定为 2β,3β,16α-trihydroxyolean-13(18)-en-23,28-dioic acid 和 2β,3β,16α-trihydroxyolean-28,13β-olide-23-oic acid 的两种主要人工合成化合物被一起获得用一些山楂酸

  DOI：

  10.1016/j.phytochem.2017.02.018
• 作为产物：
  描述：

  medicoside I 在 氢氧化钾 作用下， 以 水 为溶剂， 反应 1.0h， 以61 mg的产率得到medicoside C
  参考文献：
  名称：

  Triterpene glycosides of alfalfa. III. Medicoside I

  摘要：

  DOI：

  10.1007/bf00599263

文献信息

• New Triterpenic Saponins from the Aerial Parts of <i>Medicago arabica</i> (L.) Huds
  作者：Aldo Tava、Mariella Mella、Pinarosa Avato、Elisa Biazzi、Luciano Pecetti、Zbigniew Bialy、Marian Jurzysta

  DOI：10.1021/jf8036984

  日期：2009.4.8

  The reinvestigation of saponin composition from Medicago arabica from Italy allowed the detection of nineteen (1-19) saponins. All of them were purified by reverse-phase chromatography and their structures elucidated by spectroscopic and spectrometric (1D and 2D NMR; ESI-MS/MS) and chemical methods. Fourteen were known saponins, previously found in other plants including other Medicago, species. They have been identified as glycosides of oleanolic acid, 2 beta,3 beta-dihydroxyolean-12-en-28-oic acid, hederagenin, bayogenin and soyasapogenol B. Five saponins, identified as 3-O-[-alpha-L-arabinopyranosyl(1 -> 2)-beta-D-glucuronopyranosyl]-30-O-beta-D-glucopyranosyl 2 beta,3 beta,30-trihydroxyolean-12-en-28-oic acid (1), 3-O-[alpha-L-arabinopyranosyl(1 -> 2)-beta- -D-glucuronopyranosyl]-30-O-[beta-D-glucopyranosyl]3 beta,30-dihydroxyolean-12-en-28-oic acid (2), 3-O-[beta-D-glucuronopyranosyl]-30-O-[alpha-L-arabinopyranosyl(1 -> 2)-beta-D-glucopyranosyl]2 beta,3 beta,30-trihydroxyolean-12-en-28-oic acid (3), 3-O-[beta-D-glucuronopyranosyl]-30-O[alpha-L-arabinopyranosyl(1 -> 2)-beta-D-glucopyranosyl] 3 beta,30-dihydroxyolean-12-en-28-oic acid (4) and 3-O-[beta-D-glucuronopyranosyl]-30-O-[beta-D-glucopyranosyl] 2 beta,3 beta,30-trihydroxyolean-12-en-28-oic acid (5), are reported here as new natural compounds. These new saponins, possessing a hydroxy group at the 30-methyl position of the triterpenic skeleton, have never been previously found in the genus Medicago.
• Artefact formation during acid hydrolysis of saponins from Medicago spp.
  作者：Aldo Tava、Elisa Biazzi、Mariella Mella、Paolo Quadrelli、Pinarosa Avato

  DOI：10.1016/j.phytochem.2017.02.018

  日期：2017.6

  sapogenol artefact identified as 3β,22β,24-trihydroxyolean-18(19)-en and named soyasapogenol H. From a zanhic acid saponin two major artefact compounds identified as 2β,3β,16α-trihydroxyolean-13(18)-en-23,28-dioic acid and 2β,3β,16α-trihydroxyolean-28,13β-olide-23-oic acid were obtained, together with some zanhic acid. Other compounds, detected in very small amount in the reaction mixture, were also tentatively

  紫花苜蓿皂苷酸水解过程中获得的人工制品化合物。（豆科），已通过 GC-FID 进行监测和评估。它们的鉴定已通过 GC-MS 和 1H 和 13C NMR 进行。考虑了在三萜五环苷元上具有不同取代基的皂苷，并在 10 小时的时程反应中检测和量化了它们的水解产物。从大豆皂甙 B、C、D 和 F 中获得众所周知的大豆皂甙 B、C、D 和 F，以及先前未描述的皂甙人工制品，鉴定为 3β,22β,24-trihydroxyolean-18(19)-en 并命名为 soyasapogenol H。来自 zanhic acid saponin鉴定为 2β,3β,16α-trihydroxyolean-13(18)-en-23,28-dioic acid 和 2β,3β,16α-trihydroxyolean-28,13β-olide-23-oic acid 的两种主要人工合成化合物被一起获得用一些山楂酸
• Triterpene glycosides of alfalfa. III. Medicoside I
  作者：A. E. Timbekova、N. K. Abubakirov

  DOI：10.1007/bf00599263

  日期：1986.9