3,4,5,4’-四羟基-(E)-苯乙烯 | 331443-00-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 中文名称: 3,4,5,4’-四羟基-(E)-苯乙烯
• 中文别名: (E)-5-(4-羟基苯亚烯丙基)苯-1,2,3-三醇；4-羟基白藜芦醇
• 英文名称: 3,4,4',5-tetrahydroxy-trans-stilbene
• 英文别名: 3,4,5,4'-tetrahydroxy-trans-stilbene；3,4,4',5-trans-tetrahydroxystilbene；3,4,5,4'-tetrahydroxystilbene；4-hydroxyresveratrol；3,4,4',5-tetrahydroxystilbene；5-[(E)-2-(4-hydroxyphenyl)ethenyl]benzene-1,2,3-triol
• CAS: 331443-00-6
• 化学式: C₁₄H₁₂O₄
• 分子量: 244.247
• InChiKey: GRZOJEWQFCAKPF-OWOJBTEDSA-N

物化性质

• 沸点：
  507.8±50.0 °C(Predicted)
• 密度：
  1.468±0.06 g/cm3(Predicted)
• LogP：
  2.872 (est)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  80.9
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  [(3,4,5-trimethoxyphenyl)methyl]phosphoric acid diethyl ester 在 sodium methylate 、 三溴化硼 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.5h， 生成 3,4,5,4’-四羟基-(E)-苯乙烯
  参考文献：
  名称：

  Resveratrol analogues as selective cyclooxygenase-2 inhibitors: synthesis and structure–activity relationship

  摘要：

  Resveratrol (3,5,4'-trihydroxy-trans-stilbene) is found in grapes and various medical plants. Among cytotoxic, antifungal, antibacterial cardioprotective activity resveratrol also demonstrates non-selective cyclooxygenase-1 (COX-1) and cyclooxygenase-2 (COX-2) inhibition. In order to find more selective COX-2 inhibitors a series of methoxylated and hydroxylated resveratrol derivatives were synthesized and evaluated for their ability to inhibit both enzymes using in vitro inhibition assays for COX-1 and COX-2 by measuring PGE(2) production. Hydroxylated but not methoxylated resveratrol derivatives showed a high rate of inhibition. The most potent resveratrol compounds were 3,3',4',5-tetra-trans-hydroxystilbene (COX-1: IC50 = 4.713, COX-2: IC50 = 0.0113 muM, selectivity index = 417.08) and 3,3',4,4',5,5'-hexa-hydroxy-trans-stilbene (COX-1: IC50 = 0.748, COX-2: IC50 = 0.00104muM, selectivity index = 719.23). Their selectivity index was in part higher than celecoxib, a selective COX-2 inhibitor already established on the market (COX-1: IC50 = 19.026, COX-2: IC50 = 0.03482 muM, selectivity index = 546.41). Effect of structural parameters on COX-2 inhibition was evaluated by quantitative structure-activity relationship (QSAR) analysis and a high correlation was found with the topological surface area TPSA (r = 0.93). Docking studies on both COX-1 and COX-2 protein structures also revealed that hydroxylated but not methoxylated resveratrol analogues are able to bind to the previously identified binding sites of the enzymes. Hydroxylated resveratrol analogues therefore represent a novel class of highly selective COX-2 inhibitors and promising candidates for in vivo studies. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.08.008

文献信息

• MOLECULARLY IMPRINTED POLYMERS
  申请人：Hearn Milton T. W.

  公开号：US20120052757A1

  公开（公告）日：2012-03-01

  The present invention provides methods of designing molecularly imprinted polymers (MIPs) which have applications in extracting bioactive compounds from a range of bioprocessing feedstocks and wastes. The present invention is further directed to MIPs designed by the methods of the present invention.

  本发明提供了设计分子印迹聚合物（MIPs）的方法，这些方法在从各种生物加工原料和废弃物中提取生物活性化合物方面具有应用。本发明进一步针对由本发明方法设计的MIPs。
• Stilbene derivatives and their use in medicaments
  申请人：Szekeres Thomas

  公开号：US20070191627A1

  公开（公告）日：2007-08-16

  The invention relates to stilbene derivatives of general formula (I), in which at least four of the substituents R 1 to R 6 do not represent hydrogen. The substituents are effective radical captors, anti-tumour active ingredients and selective cyclooxygenase-2 inhibitors.

  该发明涉及一般式(I)的stilbene衍生物，其中至少有四个取代基R1至R6不代表氢。这些取代基是有效的自由基捕获剂、抗肿瘤活性成分和选择性环氧合酶-2抑制剂。
• An Efficient Synthesis of Resveratrol and a Hydroxyl Derivative via the Perkin Reaction: <i>cis</i> to <i>trans</i> Isomerisation in a Demethylation Process
  作者：Guoxing Li、Yong Zou、Xuejing Zhang

  DOI：10.3184/030823407x266234

  日期：2007.11

  Two trans polyphenolic stilbenes, Resveratrol and 3,4,4′,5- trans-tetrahydroxystilbene, were prepared in three steps from 4-methoxy phenylacetic acid and methoxylated benzaldehydes via a Perkin reaction. An interesting cis to trans isomerisation occured in the demethylation process in the presence of AlI3 and acetonitrile to give resveratrol and 3,4,4′,5-trans-tetrahydroxystilbene with overall yields

  两种反式多酚芪，白藜芦醇和 3,4,4',5- 反式四羟基芪，通过 Perkin 反应从 4-甲氧基苯乙酸和甲氧基化苯甲醛分三步制备。在 AlI3 和乙腈的存在下，在去甲基化过程中发生了有趣的顺反异构化，得到白藜芦醇和 3,4,4',5-反式四羟基芪，总产率分别为 51% 和 48%。
• Antioxidant compositions for treatment of inflammation or oxidative damage
  申请人：Perio Sciences, LLC

  公开号：US10918613B2

  公开（公告）日：2021-02-16

  One embodiment of the invention is directed to a method of preventing, reducing, or eliminating at least one negative effect of oxidative damage, such as an oral disease, caused by a dental device in the mouth of a patient. Another embodiment relates to a method of preventing, reducing, or eliminating at least one negative effect of inflammation. The method may include applying topically to a soft oral tissue in the patient an oral antioxidant composition. The antioxidant composition may include between 0.0001% and 5.0% w/w or at least one antioxidant, wherein the at least one antioxidant includes a natural phytochemcial antioxidant, a flavonoid, an anthocyanidin, a dihydrochalcone, a phenylpropanoid, a chalcone, a curcuminoid, a tannin, a stilbenoid, a coumarin, a carotenoid, or a vitamin, and an orally pharmaceutically acceptable carrier. The pH of the oral antioxidant composition may be at least 5.0.

  本发明的一个实施方案涉及一种预防、减少或消除由患者口腔中的牙科设备引起的氧化损伤（如口腔疾病）的至少一种负面影响的方法。另一个实施方案涉及一种预防、减少或消除至少一种炎症负面影响的方法。该方法可包括向患者的口腔软组织局部施用口腔抗氧化剂组合物。抗氧化剂组合物可包括 0.0001% 至 5.0% w/w 或至少一种抗氧化剂，其中至少一种抗氧化剂包括天然植物抗氧化剂、类黄酮、花青素、二氢查尔酮、苯基丙酮、查尔酮、姜黄素、单宁、链霉素、香豆素、类胡萝卜素或维生素，以及口服药物可接受载体。口服抗氧化剂组合物的 pH 值至少为 5.0。
• Resveratrol analogs for prevention of disease
  申请人：——

  公开号：US20020028852A1

  公开（公告）日：2002-03-07

  Compositions and methods for prevention or treatment of disease are provided which comprise analogs of Resveratrol.

  提供了预防或治疗疾病的组合物和方法，其中包括白藜芦醇类似物。