25-hydroxy-24-epibrassinolide | 156217-67-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: 25-hydroxy-24-epibrassinolide
• 英文别名: 25-Hydroxy-24-epi-brassinolide；(1S,2R,4R,5S,7S,11S,12S,15R,16S)-4,5-dihydroxy-2,16-dimethyl-15-[(2S,3R,4R,5S)-3,4,6-trihydroxy-5,6-dimethylheptan-2-yl]-9-oxatetracyclo[9.7.0.02,7.012,16]octadecan-8-one
• CAS: 156217-67-3
• 化学式: C₂₈H₄₈O₇
• 分子量: 496.685
• InChiKey: IGZXDKCXHICLQE-LSYAKQBXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  35
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  127
• 氢给体数：
  5
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  丙酮 、 25-hydroxy-24-epibrassinolide 在 对甲苯磺酸 作用下， 反应 1.0h， 生成 2,3,22,23-tetra-O-methyl-25-hydroxy-24-epibrassinolide
  参考文献：
  名称：

  Isolation and characterization of related impurities in 24-epibrassinolide

  摘要：

  Two extra hydroxylated analogs of 24-epibrassinolide (2),17-hydroxy-24-epibrassinolide (4), 25-hydroxy 24-epibrassinolide (5), and two oxo-analogs of 24-epibrassinolide 22-oxo-23S-24-epibrassinolide (6), 22R-23-oxo-24-epibrassinolide (7) as impurities were isolated and identified from the initial material [purity: 2 and its 22S, 23S-isomer (3) :-95%] by using various chromatographic methods and repeated crystallization. Among them, compound 4 and compound 6 were first reported. Their structures were established by spectrometric analysis and X-ray crystallography study. Formation of mixed crystals of 6 and 7 in the crystallization process was postulated and further confirmed. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.12.080
• 作为产物：
  描述：

  25-hydroxy-(22R,23R,24R)-2α,3α-diacetoxy-22,23-isopropylidenedioxy-24-methyl-5α-cholestan-6-one 在 双氧水 、 potassium carbonate 、 三氟乙酸酐 作用下， 以 甲醇 、 氯仿 为溶剂， 反应 7.0h， 生成 25-hydroxy-24-epibrassinolide
  参考文献：
  名称：

  甲基（三氟甲基）二环氧乙烷对油菜素类固醇的区域选择性氧基官能化：通过直接CH插入合成25-羟基-油菜素内酯和25-羟基-24-表油菜素内酯

  摘要：

  报道了使用甲基（三氟甲基）二环氧乙烷在位置25处合适的油菜素甾类衍生物的直接氧官能化。脱保护后与四乙酰基油菜素内酯的反应直接导致所需的25-羟基-油菜素内酯，但在（24R）系列中，22,23-异丙基二烯二氧基衍生物已被证明是25-羟基化的合适前体，从而导致25-羟基-油菜素内酯。 24-表雌甾酮和Baeyer-Villiger分别氧化成25-羟基-24-表油菜素内酯后。

  DOI：

  10.1016/0040-4020(96)00587-x

文献信息

• Role of a cytochrome P450-dependent monooxygenase in the hydroxylation of 24-epi-brassinolide
  作者：Jochen Winter、Bernd Schneider、Dieter Strack、Günter Adam

  DOI：10.1016/s0031-9422(96)00827-8

  日期：1997.5

  24-epi-Brassinolide, exogenously applied to cell suspension cultures of Lycopersicon esculentum is hydroxylated at C-25 and C-26, respectively, followed by glucosylation of the newly formed hydroxyl group. Treatment of the cell cultures with the specific cytochrome P450 inhibitors, clotrimazole and ketoconazole, resulted in a strong decrease of only the C-25 hydroxylation, whereas hydroxylation at C-26 was not affected. The common cytochrome P450 inducers, ethanol, MnCl2, phenobarbital, pregnenolone 16 alpha-carbonitrile or clofibrate, did not induce hydroxylation activity at C-25 or at C-26. In addition, substrate analogues (22S,23S-homobrassinolide, 24-epi-castasterone, ecdysone, and 20-OH-ecdysone) were not accepted. Only application of 24-epi-brassinolide and brassinolide resulted in an increased activity of both the C-25; and C-26 hydroxylases. For further examination of the molecular level of this inducing effect, the influence of the protein biosynthesis inhibitor cycloheximide has been studied. Thus, increase of both hydroxylase activities is obviously based on gene expression by action of the substrates, 24-epi-brassinolide and brassinolide. (C) 1997 Elsevier Science Ltd.
• Isolation and characterization of related impurities in 24-epibrassinolide
  作者：Hongli Chen、Huijin Feng、Yuanchao Li、Biao Jiang

  DOI：10.1016/j.tet.2008.12.080

  日期：2009.3

  Two extra hydroxylated analogs of 24-epibrassinolide (2),17-hydroxy-24-epibrassinolide (4), 25-hydroxy 24-epibrassinolide (5), and two oxo-analogs of 24-epibrassinolide 22-oxo-23S-24-epibrassinolide (6), 22R-23-oxo-24-epibrassinolide (7) as impurities were isolated and identified from the initial material [purity: 2 and its 22S, 23S-isomer (3) :-95%] by using various chromatographic methods and repeated crystallization. Among them, compound 4 and compound 6 were first reported. Their structures were established by spectrometric analysis and X-ray crystallography study. Formation of mixed crystals of 6 and 7 in the crystallization process was postulated and further confirmed. (C) 2009 Elsevier Ltd. All rights reserved.
• Regioselective oxyfunctionalization of brassinosteroids by methyl(trifluoromethyl)dioxirane: Synthesis of 25-hydroxy-brassinolide and 25-hydroxy-24-epibrassinolide by direct C-H insertion
  作者：Brunhilde Voigt、Andrea Porzel、Dieter Golsch、Waldemar Adam、Günter Adam

  DOI：10.1016/0040-4020(96)00587-x

  日期：1996.8

  The direct oxyfunctionalization of suitable brassinosteroid derivatives at position 25 using methyl(trifluoromethyl)dioxirane is reported. Whereas reaction with tetraacetyl brassinolide led after deprotection directly to the desired 25-hydroxy-brassinolide, in the (24R) series the 22,23-isopropylidenedioxy derivative has been shown to be a suitable precursor for the 25-hydroxylation leading to 25-

  报道了使用甲基（三氟甲基）二环氧乙烷在位置25处合适的油菜素甾类衍生物的直接氧官能化。脱保护后与四乙酰基油菜素内酯的反应直接导致所需的25-羟基-油菜素内酯，但在（24R）系列中，22,23-异丙基二烯二氧基衍生物已被证明是25-羟基化的合适前体，从而导致25-羟基-油菜素内酯。 24-表雌甾酮和Baeyer-Villiger分别氧化成25-羟基-24-表油菜素内酯后。