(-)-13-hydroxyglobulol | 123808-27-5

• 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: (-)-13-hydroxyglobulol
• 英文别名: 7β,14-dihydroxyaromadendrane；7α,14-dihydroxyaromadendrane；14-exohydroxyglobulol；(1S,1aR,4R,4aR,7R,7aS,7bS)-1-(hydroxymethyl)-1,4,7-trimethyl-2,3,4a,5,6,7,7a,7b-octahydro-1aH-cyclopropa[e]azulen-4-ol
• CAS: 123808-27-5
• 化学式: C₁₅H₂₆O₂
• 分子量: 238.37
• InChiKey: PEYLVIRXSYMEHY-LPZKKVOTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (-)-蓝桉醇 反应 432.0h， 以921 mg的产率得到(-)-13-hydroxyglobulol
  参考文献：
  名称：

  Glomerella cingulata 对倍半萜类化合物、(-)-globulol 和 (+)-ledol 的生物转化

  摘要：

  摘要 研究了Glomerella cingulata对(-)-球蛋白醇和(+)-ledol的生物转化。(-)-Globulol 仅产生一种在 C-13 处羟基化的产物。相比之下，(+)-ledol 产生了许多产品。主要代谢物包含由 Me-13 形成的羧基 C-11。新化合物的结构已根据其光谱数据和一些化学证据得到阐明。

  DOI：

  10.1016/s0031-9422(00)89522-9

文献信息

• Microbial oxidation of tricyclic sesquiterpenoids containing a dimethylcyclopropane ring
  作者：Wolf-Rainer Abraham、Klaus Kieslich、Burkhard Stumpf、Ludger Ernst

  DOI：10.1016/s0031-9422(00)97521-6

  日期：1992.1

  Abstract Calarene was oxidized by Bacillus megaterium and Diplodia gossypina to give allylic calarenols and calarendiols in which either of the geminal methyl groups of the cyclopropane ring was hydroxylated. Globulol was hydroxylated faster and in higher yields than calarene by both strains. In the case of this compound, vicinal diols were formed and, again, either of the geminal methyl groups was

  摘要 Calarene 被巨大芽孢杆菌和棉双歧杆菌氧化，得到烯丙基的calarenols 和calarendiol，其中环丙烷环的双生甲基中的任何一个被羟基化。Globulol 被两种菌株羟基化得更快，产率也高于卡拉烯。在这种化合物的情况下，形成了邻二醇，并且再次氧化了任何一个孪生甲基。只有细菌菌株引起 9-羟基化。耻垢分枝杆菌以良好的产量生产 globulol-14-exo-14-oic 酸。在孪生甲基中，外向取向的甲基优先被所有测试的菌株攻击。形成的一些代谢物是已知天然产物的立体异构体。
• Hydroxylation of Aromadendrane Derivatives by Mucor plumbeus†
  作者：Ricardo Guillermo、James R. Hanson、Almaz Truneh

  DOI：10.1039/a605991k

  日期：——

  Both 7α-hydroxy- and 7α,15-dihydroxy-aromadendrane are efficiently hydroxylated by Mucor plumbeus at C-14 with retention of the adjacent cyclopropane ring.

  7α-羟基和7α,15-二羟基-芳香树脂烷被铅霉有效地在C-14位进行羟基化，同时保留相邻的环丙烷环。
• The hydroxylation of globulol and 7-epiglobulol by Cephalosporium aphidicola
  作者：James R. Hanson、Peter B. Hitchcock、Revathy Manickavasagar

  DOI：10.1016/s0031-9422(00)89521-7

  日期：1994.11

  Globulol and 7-epiglobulol were shown to be hydroxylated by Cephalosporium aphidicola on one (C-14) of the methyl groups geminal to the cyclopropane ring in 48.5 and 56% yield, respectively. The significance of this hydroxylation adjacent to a cyclopropane ring is noted.
• Biotransformation of sesquiterpenoids, (−)-globulol and (+)-ledol by Glomerella cingulata
  作者：Mitsuo Miyazawa、Tomoaki Uemura、Hiromu Kameoka

  DOI：10.1016/s0031-9422(00)89522-9

  日期：1994.11

  Abstract The biotransformation of (−)-globulol and (+)-ledol by Glomerella cingulata was investigated. (−)-Globulol gave only one product which was hydroxylated at C-13. By contrast, (+)-ledol gave a number of products. The major metabolite contained a carboxylic group C-11 which was formed by Me-13. The structure of the new compound has been elucidated on the basis of its spectral data coupled with

  摘要 研究了Glomerella cingulata对(-)-球蛋白醇和(+)-ledol的生物转化。(-)-Globulol 仅产生一种在 C-13 处羟基化的产物。相比之下，(+)-ledol 产生了许多产品。主要代谢物包含由 Me-13 形成的羧基 C-11。新化合物的结构已根据其光谱数据和一些化学证据得到阐明。