(E)-2-methoxy-4,3,5-trihydroxystilbene | 629643-26-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (E)-2-methoxy-4,3,5-trihydroxystilbene
• 英文别名: 5-[(E)-2-(4-hydroxy-2-methoxyphenyl)ethenyl]benzene-1,3-diol；Gnetucleistol D
• CAS: 629643-26-1
• 化学式: C₁₅H₁₄O₄
• 分子量: 258.274
• InChiKey: CFQSTARVCGBYNJ-NSCUHMNNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  69.9
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-2-methoxy-4,3,5-trihydroxystilbene 在 双氧水 、 horseradish peroxidase 作用下， 以 水 、 丙酮 为溶剂， 反应 3.0h， 以62%的产率得到5-{(E)-2-[3-(3,5-dihydroxyphenyl)-2-(4-hydroxy-2-methoxyphenyl)-6-methoxy-2,3-dihydro-1-benzofuran-5-yl]ethenyl}benzene-1,3-diol
  参考文献：
  名称：

  二聚氧化白藜芦醇衍生物的区域选择性仿生合成

  摘要：

  氧化白藜芦醇及其甲基化衍生物作为偶联前体的制备分为四个步骤，其中 Wittig 反应和随后的异构化反应是关键步骤。氧化白藜芦醇在各种氧化条件下的偶联反应产生了复杂且不可分离的偶联产物混合物。由辣根过氧化物酶-H2O2 或 FeCl3·6H2O 在丙酮系统中催化的甲基化氧化白藜芦醇的氧化二聚化分别主要产生 8-5-偶联和 8-10-偶联二氢苯并呋喃型二聚体。这种区域选择性仿生策略可能有助于合成其他二聚氧化白藜芦醇衍生物。

  DOI：

  10.1055/s-0040-1707257
• 作为产物：
  描述：

  4-羟基-2-甲氧基苯甲醛 在 正丁基锂 、 偶氮二异丁腈 、 potassium carbonate 、 N,N-二甲基苯胺 、 二苯二硫醚 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 24.25h， 生成 (E)-2-methoxy-4,3,5-trihydroxystilbene
  参考文献：
  名称：

  二聚氧化白藜芦醇衍生物的区域选择性仿生合成

  摘要：

  氧化白藜芦醇及其甲基化衍生物作为偶联前体的制备分为四个步骤，其中 Wittig 反应和随后的异构化反应是关键步骤。氧化白藜芦醇在各种氧化条件下的偶联反应产生了复杂且不可分离的偶联产物混合物。由辣根过氧化物酶-H2O2 或 FeCl3·6H2O 在丙酮系统中催化的甲基化氧化白藜芦醇的氧化二聚化分别主要产生 8-5-偶联和 8-10-偶联二氢苯并呋喃型二聚体。这种区域选择性仿生策略可能有助于合成其他二聚氧化白藜芦醇衍生物。

  DOI：

  10.1055/s-0040-1707257

文献信息

• Process for extraction and separation of oxyresveratrol from Artocarpus lakoocha Roxb
  申请人：Council of Scientific & Industrial Research

  公开号：US10376840B2

  公开（公告）日：2019-08-13

  The present invention relates to a process for separation of oxyresveratrol molecule from the extracted solution of Artocarpus lakoocha Roxb. through membrane application. The product can be obtained in excellent yield upto 81% in case of extraction using water as solvent and can be separated from the extracted mixture upto 98% using indigenously developed nanofiltration membrane. Only the desired Trans isomer is obtained and no cis isomerization takes place during the extraction process.

  本发明涉及一种通过膜应用从拉古查树（Artocarpus lakoocha Roxb.）提取液中分离氧白藜芦醇分子的工艺。在用水作为溶剂萃取的情况下，可以获得高达 81% 的极高产率，使用自主研发的纳滤膜，可以从萃取混合物中分离出高达 98% 的产品。在萃取过程中，只能获得所需的反式异构体，而不会发生顺式异构化。
• Chemical transformations of oxyresveratrol (trans-2,4,3′,5′-tetrahydroxystilbene) into a potent tyrosinase inhibitor and a strong cytotoxic agent
  作者：Kittisak Likhitwitayawuid、Acom Sornsute、Boonchoo Sritularak、Poonsakdi Ploypradith

  DOI：10.1016/j.bmcl.2006.08.018

  日期：2006.11

  From oxyresveratrol (trans-2,4,3',5'-tetrahydroxystilbene 1), seven derivatives were prepared, including trans-2-methoxy-4,3',5'-trihydroxystilbene (2), trans-2,3'-dimethoxy-4,5'-dihydroxystilbene (3), trans-4,3'-dimethoxy-2,5'-dihydroxystilbene (4), trans-2,4,3',5'-tetramethoxystilbene (5) and cis-2,4,3',5'-tetramethoxystilbene (6), 2,4,3',5'-tetrahydroxybibenzyl (7), and 2,4,3',5'-tetramethoxybibenzyl (8). The tetrahydroxybibenzyl 7, a hydrogenation product of 1, exhibited more potent tyrosinase inhibitory activity than the parent compound, without cytotoxicity. A kinetic study revealed that 7 was a reversible and non-competitive inhibitor of mushroom tyrosinase with L-dopa as the substrate. Analysis of the K-i values indicated that 7 has a slightly higher affinity to the enzyme than 1. Compound 6, a tetra-O-methylated analogue of 1 with cis-configuration, was deprived of inhibitory effect on the enzyme tyrosinase, but showed very strong cytotoxicity against the human cancer cells KB, BC, and NCI-H187, with potency comparable to those of the anticancer agents ellipticine and doxorubicin. Data on the tyrosinase inhibitory activity and cytotoxicity of 1-8 indicated that O methylation on stilbene 1 destroyed anti-tyrosinase activity but generated cytotoxicity. Thus, facile preparations of a potent tyrosinase inhibitor (7) and a strong cytotoxic agent (6) from the natural product 1 were achieved through simple chemical reactions. (c) 2006 Elsevier Ltd. All rights reserved.
• A PROCESS FOR EXTRACTION AND SEPARATION OF OXYRESVERATROL FROM ARTOCARPUS LAKOOCHA ROXB
  申请人：Council of Scientific and Industrial Research

  公开号：EP3204346A1

  公开（公告）日：2017-08-16
• [EN] A PROCESS FOR EXTRACTION AND SEPARATION OF OXYRESVERATROL FROM ARTOCARPUS LAKOOCHA ROXB<br/>[FR] PROCÉDÉ D'EXTRACTION ET DE SÉPARATION D'OXYRESVÉRATROL D'ARTOCARPUS LAKOOCHA ROXB
  申请人：COUNCIL SCIENT IND RES

  公开号：WO2016056029A1

  公开（公告）日：2016-04-14

  The present invention relates to a process for purification of oxyresveratrol from the extracted solution of Artocarpus lakoocha Roxb through membrane separation. The product can be obtained in excellent yield up to 81% using water as extracting solvent and can be separated from the extract to up to 98% using nanofiltration membranes. Only the desired trans isomer is obtained and no cis isomerisation takes place during the extraction process.
• Regioselective Biomimetic Synthesis of Dimeric Oxyresveratrol Derivatives
  作者：Wenling Li、Lu Ran、Hongpeng Li、Ge Chao、Xiaodong Kang、Tian Lei

  DOI：10.1055/s-0040-1707257

  日期：2020.11

  Oxyresveratrol and its methylated derivative as coupling precursors were efficiently prepared in four steps, with Wittig reactions and subsequent isomerization reactions as the key steps. The coupling reactions of oxyresveratrol under various oxidative conditions gave a complex and inseparable mixture of coupling products. The oxidative dimerizations of methylated oxyresveratrols catalyzed by horseradish

  氧化白藜芦醇及其甲基化衍生物作为偶联前体的制备分为四个步骤，其中 Wittig 反应和随后的异构化反应是关键步骤。氧化白藜芦醇在各种氧化条件下的偶联反应产生了复杂且不可分离的偶联产物混合物。由辣根过氧化物酶-H2O2 或 FeCl3·6H2O 在丙酮系统中催化的甲基化氧化白藜芦醇的氧化二聚化分别主要产生 8-5-偶联和 8-10-偶联二氢苯并呋喃型二聚体。这种区域选择性仿生策略可能有助于合成其他二聚氧化白藜芦醇衍生物。