2α-hydroxystemod-12-ene | 334536-64-0

• 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: 2α-hydroxystemod-12-ene
• 英文别名: (1R,2S,4S,7S,10S,12S)-2,6,6,13-tetramethyltetracyclo[10.3.1.01,10.02,7]hexadec-13-en-4-ol
• CAS: 334536-64-0
• 化学式: C₂₀H₃₂O
• 分子量: 288.473
• InChiKey: FKJQVPKQBRWJPK-BUJXUYPKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  21
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2α-hydroxystemod-12-ene 在 palladium on activated charcoal jones reagent 、 氢气 作用下， 以 乙酸乙酯 、 丙酮 为溶剂， -18.0 ℃ 、103.42 kPa 条件下， 反应 7.0h， 生成 stemodane
  参考文献：
  名称：

  Investigation of the importance of the C-2 and C-13 oxygen functions in the transformation of stemodin analogues by Rhizopus oryzae ATCC 11145

  摘要：

  Incubation of 2alpha,13(R)-dihydroxystemodane (3) with Rhizopus oryzae ATCC 11145 gave 2alpha,7beta,13(R)-trihydroxystemodane (11) while biotransformation of 13(R)-hydroxystemodan-2-one (5) yielded 6alpha,13(R)-dihydroxystemodan-2-one (12) and 7beta,13(R)-dihydroxystemodan-2-one (13). Bioconversion of 2beta,13(R)-dihydroxystemodane (7) with Rhizopus afforded 2beta,7,13(R)-trihydroxystemodane (14). The results complement data from our previous work and provide more information about the effect of functional groups of stemodane substrates on the site of hydroxylation. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2004.05.016
• 作为产物：
  描述：

  stemodin 在 2,4,6-三甲基吡啶 作用下， 反应 96.0h， 以58.7%的产率得到2α-hydroxystemod-12-ene
  参考文献：
  名称：

  白僵菌 ATCC 7159 对二萜和二萜衍生物的生物转化

  摘要：

  白僵菌 ATCC 7159 对大黄素和大黄酮的生物羟基化分别产生了 2alpha,13,18-trihydroxystemodane 和 13,18-dihydroxystemodan-2-one。Stemarin 被转换为新型 1beta,13,19-trihydroxystemarane 和 13-hydroxystemarane-19-carb 酸。还研究了大黄素的各种衍生物的合成和生物转化。

  DOI：

  10.1016/s0031-9422(00)00403-9

文献信息

• Investigation of the importance of the C-2 oxygen function in the transformation of stemodin analogues by Rhizopus oryzae ATCC 11145
  作者：Glenroy D.A. Martin、William F. Reynolds、Paul B. Reese

  DOI：10.1016/j.phytochem.2004.01.011

  日期：2004.3

  A new stemodinoside, stemodin-a-L-arabinofuranoside (5), was isolated from the plant Stemodia maritima. Incubation of stemodin (2) with Rhizopus oryzae ATCC 11145 gave 2alpha,7beta,13(S)-trihydroxystemodane (17) and 2alpha,3beta,13(S),16alpha-tetrahydroxystemodane (18) whilst stemodinone (8) afforded 6alpha,13(S)-dihydroxystemodan-2-one (19). The bioconversion of 2beta,13(S)-dihydroxystemodane (10) by the fungus yielded 2beta,7beta,13(S)-trihydroxystemodane (20) whereas stemod-12-en-2-one (9) provided 7beta,17-dihydroxystemod-12-en-2-one (21). The results provide useful information about the relationship between the functional groups of the substrates and their potential for bioconversion. (C) 2004 Elsevier Ltd. All rights reserved.
• Biotransformation of diterpenes and diterpene derivatives by Beauveria bassiana ATCC 7159
  作者：Greg O. Buchanan、Paul B. Reese

  DOI：10.1016/s0031-9422(00)00403-9

  日期：2001.1

  The biohydroxylation of stemodin and stemodinone by Beauveria bassiana ATCC 7159 gave exclusively 2alpha,13,18-trihydroxystemodane and 13,18-dihydroxystemodan-2-one respectively. Stemarin was converted to the novel 1beta,13,19-trihydroxystemarane and 13-hydroxystemarane-19-carboxylic acid. The synthesis and biotransformation of various derivatives of stemodin have also been studied.

  白僵菌 ATCC 7159 对大黄素和大黄酮的生物羟基化分别产生了 2alpha,13,18-trihydroxystemodane 和 13,18-dihydroxystemodan-2-one。Stemarin 被转换为新型 1beta,13,19-trihydroxystemarane 和 13-hydroxystemarane-19-carb 酸。还研究了大黄素的各种衍生物的合成和生物转化。
• Investigation of the importance of the C-2 and C-13 oxygen functions in the transformation of stemodin analogues by Rhizopus oryzae ATCC 11145
  作者：G MARTIN

  DOI：10.1016/j.phytochem.2004.05.016

  日期：2004.8

  Incubation of 2alpha,13(R)-dihydroxystemodane (3) with Rhizopus oryzae ATCC 11145 gave 2alpha,7beta,13(R)-trihydroxystemodane (11) while biotransformation of 13(R)-hydroxystemodan-2-one (5) yielded 6alpha,13(R)-dihydroxystemodan-2-one (12) and 7beta,13(R)-dihydroxystemodan-2-one (13). Bioconversion of 2beta,13(R)-dihydroxystemodane (7) with Rhizopus afforded 2beta,7,13(R)-trihydroxystemodane (14). The results complement data from our previous work and provide more information about the effect of functional groups of stemodane substrates on the site of hydroxylation. (C) 2004 Elsevier Ltd. All rights reserved.