(E)-1-hydroxy-3-(4-methoxy)styrylbenzene | 110993-22-1

• 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)-1-hydroxy-3-(4-methoxy)styrylbenzene
• 英文别名: E-3-hydroxy-4'-methoxystilbene；3-hydroxy-4'-methoxystilbene；(E)-3-(4-methoxystyryl)phenol；3-[(E)-2-(4-methoxyphenyl)ethenyl]phenol
• CAS: 110993-22-1
• 化学式: C₁₅H₁₄O₂
• 分子量: 226.275
• InChiKey: PGUWMMWBXKRYFT-AATRIKPKSA-N

物化性质

• 熔点：
  159-160 °C(Solv: methanol (67-56-1); water (7732-18-5))
• 沸点：
  406.6±24.0 °C(Predicted)
• 密度：
  1.159±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  17
• 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：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-1-hydroxy-3-(4-methoxy)styrylbenzene 在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 12.0h， 以95%的产率得到3-[2-(4-甲氧基苯基)乙基]苯酚
  参考文献：
  名称：

  Berrier, Christian; Jacquesy, Jean-Claude; Renoux, Alain, Bulletin de la Societe Chimique de France, 1987, # 1, p. 212 - 218

  摘要：

  DOI：
• 作为产物：
  描述：

  4-甲氧基苄基三苯基膦溴化盐 在 正丁基锂 、 四丁基氟化铵 、 碘 作用下， 以 四氢呋喃 、 正己烷 、 正庚烷 为溶剂， 反应 16.75h， 生成 (E)-1-hydroxy-3-(4-methoxy)styrylbenzene
  参考文献：
  名称：

  Quinone reductase induction activity of methoxylated analogues of resveratrol

  摘要：

  Agents that induce the activity of phase II enzymes play an important role in intervening with the carcinogenic process at the initiation stage. Resveratrol is well known for its chemopreventive activity against major stages of carcinogenesis. In this study, several methoxylated analogues of resveratrol were synthesized and evaluated for their ability to induce the activity of the phase H enzyme quinone reductase (QR). Methoxy groups serve to increase lipophilicity and improve metabolic stability. Compared to resveratrol, analogues with ortho-metboxy substituents were found to be more potent inducers of QR and to exert their activity in a qualitatively different manner. The greater induction activities associated with these stilbenoids serve as a useful starting point for the design of improved chemopreventive agents. (c) 2007 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2006.12.012

文献信息

• Syntheses of polyfunctionalized resveratrol derivatives using Wittig and Heck protocols
  作者：Malik Chalal、Dominique Vervandier-Fasseur、Philippe Meunier、Hélène Cattey、Jean-Cyrille Hierso

  DOI：10.1016/j.tet.2012.03.025

  日期：2012.5

  protocols for Wittig reaction and palladium-catalyzed Heck coupling give expedient access to a series of unprecedented polyfunctionalized artificial-resveratrol derivatives. In the modified Wittig protocol, trimethylsilyl was used as a highly valuable protective group of the phenolic functions of starting aromatic materials. A clean O-alkylation of hydroxylated stilbenes with ethylene carbonate was

  Wittig反应和钯催化的Heck偶联的改进方案使人们可以方便地获得一系列前所未有的多官能化人工白藜芦醇衍生物。在改进的Wittig协议中，三甲基甲硅烷基被用作起始芳香族材料的酚功能的高度有价值的保护基。干净的O还进行了用碳酸亚乙酯对羟基化的对苯二甲酸酯进行的烷基化。因此，Wittig反应接着羟乙基化仅在二氧化碳作为废料的情况下一锅进行。另外，通过使用二茂铁基膦配体开发了钯催化的Heck偶联策略，并且不需要任何保护/脱保护序列就获得了多官能化的羟基苯乙烯基苯甲酸酯。这些程序最多引入六个官能团，这限制了反应步骤的数量，废物的毒性以及昂贵试剂的使用。
• Activation of anti-oxidant Nrf2 signaling by substituted trans stilbenes
  作者：Lorraine M. Deck、Lisa J. Whalen、Lucy A. Hunsaker、Robert E. Royer、David L. Vander Jagt

  DOI：10.1016/j.bmc.2017.01.005

  日期：2017.2

  is the issue of selectivity. In the present study, substituted trans stilbenes were identified as activators of Nrf2. These activators of Nrf2 are not highly electrophilic and therefore are unlikely to activate Nrf2 through covalent modification of Keap1. Dose-response studies demonstrated that a range of substituents on either ring of the trans stilbenes, especially fluorine and methoxy substituents

  Nrf2是cap'n'collar转录因子家族的成员，是II期排毒和抗氧化基因以及抗炎和神经保护基因的主要调节剂。在许多慢性疾病中炎症和氧化应激的重要性支持了抗氧化剂Nrf2信号转导可能具有治疗潜力的概念。许多Nrf2激活剂已进入临床试验。Nrf2与它的结合伴侣Keap1结合存在于胞质溶胶中，Keap1是一种富含硫醇的氧化还原传感蛋白。响应于氧化和亲电子应力，Keap1的选定半胱氨酸残基被修饰，从而将Keap1锁定在Nrf2-Keap1复合物中，并使新合成的Nrf2进入细胞核。激活Nrf2的多种化学物质，包括多种天然产物，是亲电试剂，通常通过迈克尔加成来修饰Keap1，从而导致Nrf2激活。作为Keap1的亲电子共价修饰剂的Nrf2活化剂的设计，一个需要关注的问题是选择性问题。在本研究中，替代反式斯蒂芬苯酯被鉴定为Nrf2的激活剂。这些Nrf2激活剂不是高度亲电的，因此不太可能通过Keap
• Synthesis, Antitumor Evaluation, and Apoptosis-Inducing Activity of Hydroxylated (<i>E</i>)-Stilbenes
  作者：Cedric J. Lion、Charles S. Matthews、Malcolm F. G. Stevens、Andrew D. Westwell

  DOI：10.1021/jm049238e

  日期：2005.2.1

  The parallel solution-phase synthesis of a series of 30 monohydroxylated (E)-stilbene analogues is described. In vitro screening revealed low micromolar activity (GI(50)) against the MDA MB 468 breast cancer cell line. Activity in MDA MB 468 cells correlated with the ability to induce apoptosis following drug treatment by the most potent agents in the series, e.g., 5dy and 5jy, an observation further reinforced by AnnexinV-FITC analysis and fluorescence microscopy.
• Inhibitory effect of cytotoxic stilbenes related to resveratrol on the expression of the VEGF, hTERT and c-Myc genes
  作者：Rosa Martí-Centelles、Eva Falomir、Juan Murga、Miguel Carda、J. Alberto Marco

  DOI：10.1016/j.ejmech.2015.09.014

  日期：2015.10

  A group of thirty-nine stilbene derivatives, prepared by means of Heck coupling reactions, has been investigated for their cytotoxicity, as well as for their ability to inhibit the production of the vascular endothelial growth factor (VEGF) and the activation of telomerase. The ability of these compounds to inhibit proliferation of two tumoral cell lines (HT-29 and MCF-7) and one non tumoral cell line (HEK-293) was first determined. Subsequently, we determined the capacity of the compounds to inhibit the secretion of VEGF in the aforementioned cell lines and to downregulate the expression of the VEGF, hTERT and c-Myc genes, the two latter involved in the control of the activation of telomerase. One of the synthetic stilbenes, (E)-4-(4-methoxystyryl)aniline, showed strong cytotoxicity and proved able to cause a marked decrease both in the secretion of VEGF and in the expression of the hTERT and c-Myc genes, in all cases at concentrations in the low nanomolar range. (C) 2015 Elsevier Masson SAS. All rights reserved.
• COSMETIC COMPOSITIONS AND METHODS OF USE
  申请人：K&K BIOTECH

  公开号：US20200397676A1

  公开（公告）日：2020-12-24

  The present invention relates to substituted stilbenes and dienones which exhibit unexpected dual activity, as inhibitors of NFκB and as agonists (activators) of Nrf2. In particular, these compounds show dual activity and it has been discovered that these compounds are particularly useful in the treatment of certain cosmetic applications and in rejuvenating and beautifying skin and other keratinous tissue of a subject in need. Cosmetic compositions and methods of using said compositions in combination with other components are disclosed herein.