(22R,23R)-3β,22,23-trihydroxystigmast-5-ene | 191151-42-5

• 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: (22R,23R)-3β,22,23-trihydroxystigmast-5-ene
• 英文别名: (22R,23R)-3β,22,23-trihydroxysitost-5-ene；(22R,23R)-stigmast-5-ene-3β,22,23-triol；(22r,23r)-3b,22,23-Trihydroxystigmast-5-ene；(2S,3R,4R,5S)-5-ethyl-2-[(3S,8S,9S,10R,13S,14S,17R)-3-hydroxy-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-6-methylheptane-3,4-diol
• CAS: 191151-42-5
• 化学式: C₂₉H₅₀O₃
• 分子量: 446.714
• InChiKey: SMGVSNRVGURTQV-ZLZOMJGSSA-N

物化性质

• 熔点：
  182-184 °C(Solvent: Acetonitrile)
• 沸点：
  572.1±25.0 °C(predicted)
• 密度：
  1.06±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  32
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.93
• 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：

  (22R,23R)-3β,22,23-trihydroxystigmast-5-ene 在 吡啶 、 chromium(VI) oxide 、 4-二甲氨基吡啶 、 氢氧化钾 、 lithium hydride 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 39.0h， 生成 (22R,23R)-3β,22,23-trihydroxy-stigmast-5,7-diene
  参考文献：
  名称：

  Synthesis of new Δ5-7-oxygenated and Δ5,7-unsaturated brassinosteroid analogs

  摘要：

  We report on the synthesis of the brassinosteroid analogs (22R,23R)-3 beta,7 beta,22,23-tetrahydroxy-stigmast-5-ene (13), (22R,23R)-3 beta,7 alpha,22,23-tetrahydroxy-stigmast-5-ene (15), and (22R,23R)-3 beta-22,23-trihydroxy-stigmast- 5,7-diene (18) by means of the osmium-catalyzed asymmetric dihydroxylation of intermediate 1, available from stigmasterol. This reaction sequence produced the expected (22S,23S)- and (22R,23R)-triols 6 and 7 as well as the 22,23-diketo derivatives 2 and 3. The phytohormone activity of the new brassinosteroid analogs is discussed. (C) 1997 by Elsevier Science Inc.

  DOI：

  10.1016/s0039-128x(97)00008-1
• 作为产物：
  描述：

  豆甾醇 在 吡啶 、 碘 、 溶剂黄146 、 对甲苯磺酰氯 作用下， 以 水 为溶剂， 反应 17.17h， 生成 (22R,23R)-3β,22,23-trihydroxystigmast-5-ene
  参考文献：
  名称：

  Δ5-7-Ketosterols with modified side chain: The synthesis and the effects on viability and cholesterol biosynthesis in Hep G2 cells

  摘要：

  合成的化合物包括：(22E)-30-羟基新植物甾-5,22-二烯-7-酮，(22R,23R)-3β,22,23-三羟基新植物甾-5-烯-7-酮，以及(22R,23R)-30-羟基-22,23-异丙基叉二氧基新植物甾-5-烯-7-酮。研究了所得的7-酮类固醇、7-酮胆固醇，以及(22S,23S)-3β-羟基-22,23-氧化新植物甾-5-烯-7-酮在肝癌细胞株Hep G2中的细胞毒性和对胆固醇生物合成的影响。

  DOI：

  10.1134/s1068162006050141

文献信息

• Synthesis and Characterization of Stigmasterol Oxidation Products
  作者：David A. Foley、Yvonne O’Callaghan、Nora M. O’Brien、Florence O. McCarthy、Anita R. Maguire

  DOI：10.1021/jf9024745

  日期：2010.1.27

  The synthesis and structural characterization of a series of oxides of stigmasterol is described providing a valuable series of reference standards for these oxides, analogous to the cholesterol oxidation products (COPs) which have been shown to have detrimental biological effects. Biological evaluation of the oxides of phytosterols is significant in the context of increased dietary use of phytosterols

  描述了一系列豆甾醇的氧化物的合成和结构表征，为这些氧化物提供了一系列有价值的参考标准，类似于已证明具有有害生物作用的胆固醇氧化产物（COP）。在饮食中增加植物甾醇的使用以降低胆固醇吸收的情况下，对植物甾醇的氧化物的生物学评估是重要的。
• Cytotoxic derivatives of (22R,23R)-dihydroxystigmastane
  作者：F. V. Drozdov、A. P. Mekhtiev、G. E. Morozevich、V. P. Timofeev、A. Yu. Misharin

  DOI：10.1134/s1068162007030090

  日期：2007.5

  (22R,23R)-22,23-dihydroxystigmast-4-en-3-one, (22R,23R)-22,23-dihydroxystigmast-4-en-3,6-dione, (22R,23R)-3 beta,5 alpha,6 beta,22,23-pentahydroxystigmastane, (22R,23R)-5 alpha,6 alpha-oxido-3 beta,22,23-trihydroxystigmastane, (22R,23R)-5 beta,6 beta-oxido-3 beta,22.23-trihydroxystigmastane, and (22R,23R)3 beta,6 beta,22,23-tetrahydroxystigmast-4-ene were synthesized. Their cytotoxicities were comparatively studied using the MCF-7 line of carcinoma cells of human mammary gland and cells of human hepatoma of the Hep G2 line.

  (22R,23R)-22,23-二羟基白 World-4-烯-3-酮、(22R,23R)-22,23-二羟基白 World-4-烯-3,6-二酮、(22R,23R)-3β,5α,6β,22,23-五羟基白 World烷、(22R,23R)-5α,6α-氧化-3β,22,23-三羟基白 World烷、(22R,23R)-5β,6β-氧化-3β,22,23-三羟基白 World烷以及(22R,23R)-3β,6β,22,23-四羟基白 World-4-烯被成功合成。这些化合物的细胞毒性通过使用人乳腺癌MCF-7细胞系和人肝癌Hep G2细胞系进行了比较研究。
• Synthesis and cytotoxicity evaluation of 22,23-oxygenated stigmastane derivatives
  作者：Alexander Yu. Misharin、Arif R. Mehtiev、Galina E. Morozevich、Yaroslav V. Tkachev、Vladimir P. Timofeev

  DOI：10.1016/j.bmc.2007.10.056

  日期：2008.2.1

  Starting from (22E)-3 alpha,5 alpha-cyclo-6 beta-methoxystigmast-22-ene eighteen derivatives of (22S,23S)-22,23-oxidostigmastane, (22R,23R)-22,23-oxidostigmastane, and (22R,23R)-22,23-dihydroxystigmastane were synthesized and screened for cytotoxicity in human hepatoma Hep G2 cells and human breast carcinoma MCF-7 cells using MTT assay. Four compounds of this series exhibited high cytotoxicity in both cells; three compounds were selectively toxic in MCF-7 cells, one compound was toxic in Hep G2 cells, rather than in MCF-7 cells; four compounds at low concentrations increased MTT test values over the control. (C) 2007 Elsevier Ltd. All rights reserved.
• Configurational assignment of brassinosteroid sidechain by exciton coupled circular dichroic spectroscopy
  作者：Akira Kawamura、Nina Berova、Koji Nakanishi、Brunhilde Voigt、Günter Adam

  DOI：10.1016/s0040-4020(97)00709-6

  日期：1997.9

  A microscale method was developed to determine the sidechain configuration of brassinosteroids, a class of potent plant growth promoters. Microscale naphthoylation followed by circular dichroic (CD) spectroscopy measurement in acetonitrile unambiguously differentiate between the two possible vicinal syn-diol configurations, (22R,23R) and (22S,23S). (C) 1997 Elsevier Science Ltd.