5,4'-di-O-hexanoyl-genistein | 918158-58-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异黄酮类化合物
• 英文名称: 5,4'-di-O-hexanoyl-genistein
• 英文别名: 5,4'-dihexanoylgenistein；4',5-di-O-hexanoylgenistein；[4-(5-Hexanoyloxy-7-hydroxy-4-oxochromen-3-yl)phenyl] hexanoate
• CAS: 918158-58-4
• 化学式: C₂₇H₃₀O₇
• 分子量: 466.531
• InChiKey: YXVFZNUNVBCXTB-UHFFFAOYSA-N

物化性质

• 熔点：
  145 °C
• 沸点：
  640.0±55.0 °C(Predicted)
• 密度：
  1.211±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  34
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  99.1
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  5,4'-di-O-hexanoyl-genistein 在 4 A molecular sieve 、 三氟化硼乙醚 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 生成 染料木碱7-beta-D-葡糖苷酸
  参考文献：
  名称：

  A facile synthesis of isoflavone 7-O-glucuronides

  摘要：

  An efficient method is presented for the synthesis of isoflavone 7-glucuronides using a N-(4-methoxyphenyl)-trifluoroacetimidate glucuronsyl donor. A 4-hexanoyl derivative of the isoflavone is used in the coupling reaction, both for protection and to improve solubility. These glucuronides are the human metabolites of estrogenic dietary isotlavones, but their biological activity and pharmacokinetics have yet to be established as until now there were no good methods for their synthesis. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.10.034
• 作为产物：
  描述：

  染料木素 在 吡啶 、 咪唑 、 苯硫酚 作用下， 以 N-甲基吡咯烷酮 为溶剂， 反应 23.0h， 生成 5,4'-di-O-hexanoyl-genistein
  参考文献：
  名称：

  两种生物活性异黄酮糖苷Talosin A和B的合成

  摘要：

  Talosin A和B，即染料木素7‐ O ‐ α ‐ L ‐6‐脱氧塔洛吡喃糖苷和染料木素4′，7‐di‐ O ‐ α ‐ L ‐‐6‐脱氧塔洛吡喃糖苷，显示出优异的抗真菌和抗炎活性，简明扼要。

  DOI：

  10.1002/cjoc.201090291

文献信息

• An Efficient Method for the Glycosylation of Isoflavones
  作者：Nawaf Al-Maharik、Nigel P. Botting

  DOI：10.1002/ejoc.200800803

  日期：2008.11

  A new efficient, high-yielding glycosylation procedure is described for isoflavones, which employs 2,2,2-trifluoro-N-(p-methoxyphenyl)acetamidates as the glycosyl donors. This methodology was used to prepare the 7-O-glycosides of the three main isoflavones, daidzein, genistein and glycitein. The isoflavones were protected with hexanoyl groups which improved their solubility in organic solvents and

  异黄酮植物雌激素因其正面和负面的健康益处而受到当前的关注。然而，关于它们的吸收、代谢和生物利用度，仍有许多悬而未决的问题。该领域的研究需要获取异黄酮 7-O-葡萄糖苷（在植物中发现的形式）和 7-O-葡萄糖醛酸苷（它们是重要的哺乳动物代谢物）的样本。描述了一种新的高效、高产的异黄酮糖基化程序，它采用 2,2,2-三氟-N-（对甲氧基苯基）乙酰胺作为糖基供体。该方法用于制备三种主要异黄酮、黄豆苷元、染料木黄酮和黄豆黄素的 7-O-糖苷。异黄酮用己酰基保护，这提高了它们在有机溶剂中的溶解度并提高了反应效率。然后采用相同的方法合成类似的 7-O-葡糖苷酸。新的合成将为进一步的生物学研究提供大量这些化合物。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)
• Highly regioselective dehexanoylation in fully hexanoylated flavonoids
  作者：Zhiwei Zheng、Ziyi Han、Li Cai、Dandan Zhou、Bryson R. Chavis、Changsheng Li、Qiang Sui、Kaiyuan Jiang、Qi Gao

  DOI：10.1016/j.tetlet.2018.11.015

  日期：2018.12

  Highly selective removal of the 7-O-hexanoyl group in fully hexanoylated flavones, isoflavones, flavanone, and flavonol was achieved under mild conditions using K2CO3 in a 1:1 mixture of CH3OH-CH2Cl2. The resulting 7-OH flavonoids are valuable intermediates for the synthesis of flavonoid 7-O-glycosides via phase-transfer-catalyzed (PTC) glycosylation. (C) 2018 Elsevier Ltd. All rights reserved.
• A facile synthesis of isoflavone 7-O-glucuronides
  作者：Nawaf Al-Maharik、Nigel P. Botting

  DOI：10.1016/j.tetlet.2006.10.034

  日期：2006.12

  An efficient method is presented for the synthesis of isoflavone 7-glucuronides using a N-(4-methoxyphenyl)-trifluoroacetimidate glucuronsyl donor. A 4-hexanoyl derivative of the isoflavone is used in the coupling reaction, both for protection and to improve solubility. These glucuronides are the human metabolites of estrogenic dietary isotlavones, but their biological activity and pharmacokinetics have yet to be established as until now there were no good methods for their synthesis. (c) 2006 Elsevier Ltd. All rights reserved.
• Synthesis of Talosin A and B, Two Bioactive Isoflavonoid Glycosides
  作者：Zhongtao Wu、Gaoyan Lian、Biao Yu、Zhenzhong Wang、Yiwu Zhao、Wei Xiao

  DOI：10.1002/cjoc.201090291

  日期：2010.9

  Talosin A and B, namely genistein 7‐O‐α‐L‐6‐deoxy‐talopyranoside and genistein 4′,7‐di‐O‐α‐L‐6‐deoxy‐talopyranoside, which show excellent antifungal and anti‐inflammatory activities, were synthesized concisely.

  Talosin A和B，即染料木素7‐ O ‐ α ‐ L ‐6‐脱氧塔洛吡喃糖苷和染料木素4′，7‐di‐ O ‐ α ‐ L ‐‐6‐脱氧塔洛吡喃糖苷，显示出优异的抗真菌和抗炎活性，简明扼要。