1β,4β,6β-trihydroxyeudesmane | 95457-15-1

• 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: 1β,4β,6β-trihydroxyeudesmane
• 英文别名: (1R,4S,4aS,5R,6S,8aR)-4,8a-dimethyl-6-propan-2-yl-1,2,3,4a,5,6,7,8-octahydronaphthalene-1,4,5-triol
• CAS: 95457-15-1
• 化学式: C₁₅H₂₈O₃
• 分子量: 256.386
• InChiKey: SFPWDWLORNWKSK-ZYIYBEKCSA-N

物化性质

• 沸点：
  380.4±42.0 °C(Predicted)
• 密度：
  1.092±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  60.7
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1β,4β,6β-trihydroxyeudesmane 以2%的产率得到
  参考文献：
  名称：

  GARCIA-GRANADOS, ANDRES;MARTINEZ, ANTONIO;ONORATO, ESTHER;RIVAS, FRANCISC+, TETRAHEDRON, 47,(1991) N, C. 91-102

  摘要：

  DOI：
• 作为产物：
  描述：

  1β,4β-dihydroxy-6β-acetoxy-eudesmane 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以92%的产率得到1β,4β,6β-trihydroxyeudesmane
  参考文献：
  名称：

  倍半萜的改善的微生物羟基化：半合成，环状亚硫酸盐和阿魏糖的衍生物的结构测定和生物转化研究。

  摘要：

  已经研究了两种新的环状亚硫酸盐奥德斯曼衍生物。它们的（R）和（S）硫构型及其“ A”环的结构排列已通过其13C和1H NMR化学位移进行了指认，并已通过单晶X射线分析得到证实。已使用羟基化真菌黑根霉（Rhizopus nigricans）研究了这些差向异构体环状亚硫酸盐及其二羟基Eudesmane前体的微生物转化。已经发现两种环亚硫酸盐阿联苯醚的生物催化速率提高和生物转化的显着差异。从（S）-非对映异构体的生物转化中分离出有希望的8alpha，11-二羟基衍生物。

  DOI：

  10.1039/b301577g

文献信息

• Sesquiterpenes from two subspecies of Sideritis varoi
  作者：Andrés García-Granados、Antonio Molina、Antonio Sáenz de Buruaga、Juan Manuel Sáenz de Buruaga

  DOI：10.1016/s0031-9422(00)80815-8

  日期：1985.1

  Abstract Two subspecies of Sideritis varoi afforded, in addition to previously reported diterpenes, the following series of new eudesmane and eudesmene acetates: 1β-hydroxy-6β-acetoxy-eudesm-4(15)-ene; 1β,4β-dihydroxy-6β-acetoxy-eudesmane; 1β-hydroxy-6β-acetoxy-eudesm-3-ene; 1β-hydroxy-6β-acetoxy-eudesm-4-ene. The structures of these compounds were elucidated by chemical and spectroscopic means.

  摘要 除了先前报道的二萜外，Sideritis varoi 的两个亚种还提供了以下一系列新的eudesmane 和eudesmene 醋酸盐：1β-羟基-6β-乙酰氧基-eudesm-4(15)-ene；1β-羟基-6β-乙酰氧基-eudesm-4(15)-烯；1β,4β-dihydroxy-6β-acetoxy-eudesmane; 1β-羟基-6β-乙酰氧基-eudesm-3-烯；1β-羟基-6β-乙酰氧基-eudesm-4-ene。通过化学和光谱手段阐明了这些化合物的结构。
• Biotransformation of 4β-hydroxyeudesmane-1,6-dione by Gliocladium roseum and Exserohilum halodes
  作者：Andrés Garcı́a-Granados、Marı́a C. Gutiérrez、Francisco Rivas、José M. Arias

  DOI：10.1016/s0031-9422(01)00340-5

  日期：2001.11

  Biotransformation of sesquiterpene 4 beta -hydroxyeudesmane-1,6-dione by the filamentous fungi Gliocladium roseum and Exserohilum halodes was achieved. With Exserohilum halodes, only one metabolite was obtained, as a result of the regio- and stereoselective reduction of the keto group at C-1, which is difficult to achieve by chemical means. Five metabolites were produced with Gliocladium roseum, three of which, the 7 alpha -hydroxylated, the 7 alpha, 11- and the 1 alpha ,8 alpha -dihydroxylated derivatives, have not previously been reported, The hydroxylation at C-1 I is the main action of this microorganism, These 11-hydroxylated compounds can be chemically transformed into 6 beta ,12-eudesmanolides. (C) 2001 Published by Elsevier Science Ltd.
• GARCIA-GRANADOS, ANDRES;MARTINEZ, ANTONIO;ONORATO, ESTHER;RIVAS, FRANCISC+, TETRAHEDRON, 47,(1991) N, C. 91-102
  作者：GARCIA-GRANADOS, ANDRES、MARTINEZ, ANTONIO、ONORATO, ESTHER、RIVAS, FRANCISC+

  DOI：——

  日期：——
• Improved microbiological hydroxylation of sesquiterpenoids: semisynthesis, structural determination and biotransformation studies of cyclic sulfite eudesmane derivatives
  作者：Andrés García-Granados、María C. Gutiérrez、Francisco Rivas

  DOI：10.1039/b301577g

  日期：——

  Two new cyclic sulfite eudesmane derivatives have been investigated. Their (R) and (S) sulfur configuration and the structural arrangement of their "A" rings have been assigned by means of their 13C and 1H NMR chemical shifts and have been confirmed by single-crystal X-ray analyses. Microbial-transformation of these epimer cyclic sulfites and their dihydroxyeudesmane precursor have been studied using

  已经研究了两种新的环状亚硫酸盐奥德斯曼衍生物。它们的（R）和（S）硫构型及其“ A”环的结构排列已通过其13C和1H NMR化学位移进行了指认，并已通过单晶X射线分析得到证实。已使用羟基化真菌黑根霉（Rhizopus nigricans）研究了这些差向异构体环状亚硫酸盐及其二羟基Eudesmane前体的微生物转化。已经发现两种环亚硫酸盐阿联苯醚的生物催化速率提高和生物转化的显着差异。从（S）-非对映异构体的生物转化中分离出有希望的8alpha，11-二羟基衍生物。