Vernonioside B₁ | 135247-99-3

• 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: Vernonioside B₁
• 英文别名: (3S,4R,5S)-3-[(3S,5S,10S,13R,14R,17R)-10,13-dimethyl-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,3,4,5,6,12,14,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-17-yl]-4-hydroxy-5-[(2R,3S)-3-methyl-2-propan-2-yloxiran-2-yl]oxolan-2-one
• CAS: 135247-99-3
• 化学式: C₃₅H₅₂O₁₀
• 分子量: 632.792
• InChiKey: YKINJEMJMIWNSA-DTTZRFTHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  45
• 可旋转键数：
  6
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  158
• 氢给体数：
  5
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  Vernonioside B₁ 在 盐酸 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 6.0h， 以3.8 mg的产率得到(3S,3aR,6R,6aS)-6-Hydroxy-3-((3S,5S,10S,13R,17R)-3-hydroxy-10,13-dimethyl-2,3,4,5,6,7,10,11,12,13,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl)-6-isopropyl-5-methyl-tetrahydro-furo[3,2-b]furan-2-one
  参考文献：
  名称：

  Bitter steroid glucosides, vernoniosides A1, A2, and A3, and related B1 from a possible medicinal plant, Vernonia amygdalina, used by wild chimpanzees.

  摘要：

  From Vernonia amygdalina, a possible medicinal plant used by wild chimpanzees, three bitter steroid glucosides, vernoniosides A1,A2 and A3 and a nonbitter vernonioside B1, were isoluted. The oxygenation patterns of the aglycone parts were new, especially the pattern of the carboxyl group at C21. The oxygen functionalities at C16 were important for the bitter taste.

  DOI：

  10.1016/s0040-4020(01)88123-0