7β-hydroxysitost-5-en-3β-yl acetate | 881413-59-8

• 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: 7β-hydroxysitost-5-en-3β-yl acetate
• 英文别名: 3β-acetoxy-7β-hydroxystigma-5-ene；3β-acetoxysitost-5-ene-7β-ol
• CAS: 881413-59-8
• 化学式: C₃₁H₅₂O₃
• 分子量: 472.752
• InChiKey: HZXJZOYEEKCCRD-BMWJOPFBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.57
• 重原子数：
  34.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  46.53
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  7β-hydroxysitost-5-en-3β-yl acetate 在 sodium carbonate 作用下， 以 甲醇 、 水 为溶剂， 以76%的产率得到5-stigmasten-3β,7β-diol
  参考文献：
  名称：

  Gram-scale chromatographic purification of β-sitosterolSynthesis and characterization of β-sitosterol oxides

  摘要：

  An effective purification method for P-sitosterol was developed starting from a commercial source of a phytosterol mixture using preparative adsorption column chromatography. P-Sitosterol (>= 95% purity) was obtained on a gram-scale. Thus, the synthesis of six P-sitosterol oxides, including 7 alpha-hydroxy, 7 beta-hydroxy, 5,6 alpha-epoxy, 5,6 beta-epoxy, 7-keto, and 5 alpha,6 beta-dihydroxysitosterol, were successfully carried out. The spectral characteristics of all the synthetic intermediates and target compounds (similar to 95% purity) were well-documented. (c) 2005 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2005.06.003
• 作为产物：
  描述：

  β-谷甾醇乙酸酯 在 sodium tetrahydroborate 、 cerium(III) chloride 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 甲醇 、 苯 为溶剂， 反应 22.25h， 生成 7β-hydroxysitost-5-en-3β-yl acetate
  参考文献：
  名称：

  Gram-scale chromatographic purification of β-sitosterolSynthesis and characterization of β-sitosterol oxides

  摘要：

  An effective purification method for P-sitosterol was developed starting from a commercial source of a phytosterol mixture using preparative adsorption column chromatography. P-Sitosterol (>= 95% purity) was obtained on a gram-scale. Thus, the synthesis of six P-sitosterol oxides, including 7 alpha-hydroxy, 7 beta-hydroxy, 5,6 alpha-epoxy, 5,6 beta-epoxy, 7-keto, and 5 alpha,6 beta-dihydroxysitosterol, were successfully carried out. The spectral characteristics of all the synthetic intermediates and target compounds (similar to 95% purity) were well-documented. (c) 2005 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2005.06.003

文献信息

• Sterols as Anticancer Agents: Synthesis of Ring-B Oxygenated Steroids, Cytotoxic Profile, and Comprehensive SAR Analysis
  作者：João F. S. Carvalho、M. Manuel Cruz Silva、João N. Moreira、Sérgio Simões、M. Luisa Sá e Melo

  DOI：10.1021/jm1007769

  日期：2010.11.11

  The cytotoxicity of oxysterols was systematically studied in tumor and normal cells. Synthetic strategies to prepare this library included oxidations at ring B and a new method to yield 6 beta-hemiphthalates directly from Delta(5)-steroids. Most oxysterols were cytotoxic and showed selectivity toward cancer cells, LAMA-84 cells (leukemia) being particularly sensitive to 4, 8, 22, and 27 (IC50 < 5.6 mu M). The structural requirements to induce selective toxicity are discussed to shed light on the development of new anticancer drugs.
• Synthesis of highly pure oxyphytosterols and (oxy)phytosterol esters
  作者：Diane Julien-David、Philippe Geoffroy、Eric Marchioni、Françis Raul、Dalal Aoudé-Werner、Michel Miesch

  DOI：10.1016/j.steroids.2008.04.010

  日期：2008.10

  Several efficient synthetic routes giving readily access to (oxy)-sitosterol esters and (oxy)cholesterol esters derived respectively from oleic acid and from 9,10-dihydroxystearic acid were developed for the first time. This approach allowed that sufficient amounts of the latter were available in order to carry out further biological studies. (c) 2008 Elsevier Inc. All rights reserved.