2,2'-亚甲基二(3,6-二羟基-5-十一烷基-2,5-环己二烯-1,4-二酮) | 4370-68-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 2,2'-亚甲基二(3,6-二羟基-5-十一烷基-2,5-环己二烯-1,4-二酮)
• 英文名称: vilangin
• 英文别名: 2-[(2,5-dihydroxy-3,6-dioxo-4-undecylcyclohexa-1,4-dien-1-yl)methyl]-3,6-dihydroxy-5-undecylcyclohexa-2,5-diene-1,4-dione
• CAS: 4370-68-7
• 化学式: C₃₅H₅₂O₈
• 分子量: 600.793
• InChiKey: SSBANIVTGNXXSJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.9
• 重原子数：
  43
• 可旋转键数：
  22
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.66
• 拓扑面积：
  149
• 氢给体数：
  4
• 氢受体数：
  8

安全信息

• 海关编码：
  2914690090

反应信息

• 作为反应物：
  描述：

  2,2'-亚甲基二(3,6-二羟基-5-十一烷基-2,5-环己二烯-1,4-二酮) 在 sodium hydroxide 作用下， 生成 2-oxotetradecanoic acid
  参考文献：
  名称：

  Chemical Examination of Embelia ribes. I. Isolation of a New Constituent, “Vilangin,” Its Constitution and Synthesis

  摘要：

  DOI：

  10.1021/jo01069a079
• 作为产物：
  描述：

  2,5-二羟基-1,4-苯喹酮 在 溶剂黄146 作用下， 以 1,4-二氧六环 为溶剂， 生成 2,2'-亚甲基二(3,6-二羟基-5-十一烷基-2,5-环己二烯-1,4-二酮)
  参考文献：
  名称：

  栓子化学成分的检验—III：一种新的维生素A合成

  摘要：

  进行了新的全草胶合成。

  DOI：

  10.1016/s0040-4020(01)92748-6

文献信息

• Molecular docking studies, in vitro-brine shrimp lethal assay and antibacterial assessment of embelin, vilangin and phenyl vilangin against endodontic pathogen, Enterococcus faecalis
  作者：S. Jayalakshmi、K. Narendran、E. Sukumar、J. Irshad Ahamed、M. S. Nivedhitha、S. Rajesh Kumar

  DOI：10.1007/s11164-021-04559-8

  日期：2021.11

  Complete debridement and disinfection of the root canal system are the primary requirement for successful endodontic treatment. Enterococcus faecalis is the most commonly found organism in a high percentage of root canal failures as a single organism or as a major component of the flora. Primary goal of this study is to assess the antibacterial effect of phytochemical agents namely embelin, vilangin and phenyl vilangin, respectively, against E. faecalis. And this is the first time that these materials are reported for antibacterial activity against the pathogen, E. faecalis. Our second goal is to predict the interaction between the active structure and the protein in the binding mode, and the third goal is to screen for cytotoxicity by brine shrimp lethality bioassay. All the compounds showed low to elevated level of antibacterial activity. Particularly, compound embelin, as well as its combination with NaOCl in the ratio 1:1, exhibits zone of inhibition value of 29 ± 0.89 and 32 ± 0.98 mm at a concentration of 80 µL and the MIC value of embelin was found to be 78.10 µg/mL. All the compounds exhibit low toxicity to high toxicity. The LC50 value of tested compounds was in the range of 17.5–80.0 µL with respect to positive control (vincristine sulphate). The result of lethality reveals the phenyl vilangin exhibits very minimal toxicity even under higher concentration, and in future, it may be investigated further for biocompatibility studies. The results of molecular docking reveal that embelin showed good interaction against 2JER protein with a higher binding energy value of − 7.2. Hence, these finding reveals that embelin and phenyl vilangin may be used as root canal irrigants in future.

  根管系统的彻底清创和消毒是成功进行根管治疗的首要条件。在大量根管治疗失败的病例中，粪肠球菌是最常见的微生物，它既可以是单一的微生物，也可以是菌群的主要成分。本研究的主要目的是评估植物化学制剂（即栓皮苷、蔓越桔皮苷和苯基蔓越桔皮苷）对粪肠球菌的抗菌效果。这是首次报道这些材料对病原体粪肠球菌的抗菌活性。我们的第二个目标是预测活性结构与蛋白质在结合模式下的相互作用，第三个目标是通过卤虾致死生物测定筛选细胞毒性。所有化合物都显示出较低到较高水平的抗菌活性。特别是化合物栓皮苷，以及其与 NaOCl 以 1:1 的比例组合，在浓度为 80 µL 时的抑菌区值分别为 29 ± 0.89 和 32 ± 0.98 mm，栓皮苷的 MIC 值为 78.10 µg/mL。所有化合物都表现出低至高的毒性。与阳性对照（硫酸长春新碱）相比，受试化合物的 LC50 值在 17.5-80.0 µL 之间。致死率结果表明，即使在较高浓度下，苯基紫兰素的毒性也非常小，今后可进一步研究其生物相容性。分子对接结果表明，栓皮苷与 2JER 蛋白有良好的相互作用，其结合能值较高，为-7.2。因此，这些研究结果表明，栓皮磷脂和苯基紫罗兰素今后可用作根管灌洗剂。
• Chemical examination of embelia ribes—III
  作者：Ch. Bheemasankara Rao、V. Venkateswarlu

  DOI：10.1016/s0040-4020(01)92748-6

  日期：1962.1

  A new total synthesis of vilangin is effected.

  进行了新的全草胶合成。
• Chemical Examination of Embelia ribes. I. Isolation of a New Constituent, “Vilangin,” Its Constitution and Synthesis
  作者：CH. BHEEMASANKARA RAO、V. VENKATESWARLU

  DOI：10.1021/jo01069a079

  日期：1961.11