白藜芦醇3,4’-二乙酸酯 | 861446-14-2

• 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: 白藜芦醇3,4’-二乙酸酯
• 英文名称: 3,4'-di-O-acetylresveratrol
• 英文别名: (E)-4-(3-Acetoxy-5-hydroxystyryl)phenyl acetate；[4-[(E)-2-(3-acetyloxy-5-hydroxyphenyl)ethenyl]phenyl] acetate
• CAS: 861446-14-2
• 化学式: C₁₈H₁₆O₅
• 分子量: 312.322
• InChiKey: IUHAHFQLCDVRJQ-ONEGZZNKSA-N

物化性质

• 熔点：
  137-139°C
• 沸点：
  505.7±50.0 °C(Predicted)
• 密度：
  1.267±0.06 g/cm3(Predicted)
• 溶解度：
  DMSO（微溶）、甲醇（微溶、超声处理）

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  白藜芦醇3,4’-二乙酸酯 在 四氮唑 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 4.25h， 生成
  参考文献：
  名称：

  Synthesis of amphiphilic resveratrol lipoconjugates and evaluation of their anticancer activity towards neuroblastoma SH-SY5Y cell line

  摘要：

  Resveratrol, a polyphenol present in grapes and other edible plants, possesses several important pharmacological activities, including anticancer activity. Nevertheless, its therapeutic use is still limited because of some unfavourable physicochemical and pharmacokinetic properties, mainly, poor cellular uptake and too rapid metabolism resulting in elimination from the body. To meet these drawbacks, some resveratrol conjugates would be useful, which would possess improved stability, uptake and bioavailability than the lead compound, and the ability to release it once it is internalized into the cell. In this paper we report a synthetic strategy which allowed us to obtain new amphiphilic resveratrol derivatives starting from different selectively protected resveratrol phosphoramidites or even from the resveratrol triphosphoramidite. Specifically, resveratrol was conjugated through phosphate bridge(s) to different lipophilic groups related to membrane lipids, such as cholesteryl or diacylglycero moieties. All the new lipoconjugates were tested towards human neuroblastoma SH-SY5Y cells and proved to be significantly more active than resveratrol, with a concentration-dependent activity. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.04.038
• 作为产物：
  描述：

  白藜芦醇 在 吡啶 、 silica gel 作用下， 以 甲醇 、 二氯甲烷 、 甲基叔丁基醚 为溶剂， 反应 64.0h， 生成 白藜芦醇3,4’-二乙酸酯
  参考文献：
  名称：

  Synthesis of amphiphilic resveratrol lipoconjugates and evaluation of their anticancer activity towards neuroblastoma SH-SY5Y cell line

  摘要：

  Resveratrol, a polyphenol present in grapes and other edible plants, possesses several important pharmacological activities, including anticancer activity. Nevertheless, its therapeutic use is still limited because of some unfavourable physicochemical and pharmacokinetic properties, mainly, poor cellular uptake and too rapid metabolism resulting in elimination from the body. To meet these drawbacks, some resveratrol conjugates would be useful, which would possess improved stability, uptake and bioavailability than the lead compound, and the ability to release it once it is internalized into the cell. In this paper we report a synthetic strategy which allowed us to obtain new amphiphilic resveratrol derivatives starting from different selectively protected resveratrol phosphoramidites or even from the resveratrol triphosphoramidite. Specifically, resveratrol was conjugated through phosphate bridge(s) to different lipophilic groups related to membrane lipids, such as cholesteryl or diacylglycero moieties. All the new lipoconjugates were tested towards human neuroblastoma SH-SY5Y cells and proved to be significantly more active than resveratrol, with a concentration-dependent activity. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.04.038

文献信息

• [EN] NITROXIDE CONTAINING AMYLOID BINDING AGENTS FOR IMAGING AND THERAPEUTIC USES<br/>[FR] AGENTS DE LIAISON À L'AMYLOÏDE CONTENANT DU NITROXYDE UTILISÉS EN IMAGERIE ET À DES FINS THÉRAPEUTIQUES
  申请人：UNIV CALIFORNIA

  公开号：WO2017031239A1

  公开（公告）日：2017-02-23

  The present invention provides methods of using nitroxide spin-labeled amyloid beta-binding compounds to image amyloid. The present invention also provides nitroxide spin-labeled amyloid beta-binding compounds

  本发明提供了使用亚硝基自旋标记的淀粉样β结合化合物来成像淀粉样物质的方法。本发明还提供了亚硝基自旋标记的淀粉样β结合化合物。
• 一类紫杉醇衍生物及其在制备防治人恶性肿瘤药物中的用途
  申请人：天津仁雨生物科技有限公司

  公开号：CN111777577A

  公开（公告）日：2020-10-16

  本发明公开了一类紫杉醇衍生物，具有通式(I)所示的结构以及其光学异构体，非对映异构体和消旋体混合物，其药学上可接受的盐。本发明进一步公开了紫杉醇衍生物及其药学上可接受盐在制备抗肿瘤药物中的应用。主要包括肺癌、乳腺癌、卵巢癌、胃癌、结直肠癌，实验结果显示：紫杉醇衍生物在体内的毒性较低，对所描述的肿瘤细胞抑制效果较明显，具备进一步深入研究的潜在价值。
• Novel Sirtuin Activating Compounds and Methods for Making the Same
  申请人：Andrus Merritt B.

  公开号：US20080255382A1

  公开（公告）日：2008-10-16

  The present invention includes methods for preparing resveratrol, resveratrol esters and substituted and unsubstituted stilbenes of the formula given below; where each Y is —O or halogen, each Z is —O or halogen, each n and each m is independently the value of 0, 1, 2, 3, 4 or 5, each A and each B is independently selected from P n , R or absent, each V and each W is independently selected from P n , straight or branched alkyl of from (2) to (6) carbon atoms and cycloalkyl of from (3) to (8) carbon atoms, alkoxy, phenyl, benzyl or halogen, R is independently selected from the group comprising alkyl with at least one carbon atom, aryl and aralkyl, P n is an alcohol protecting group and diastereoisomers of the foregoing. The compounds are made from a multi-step process including a N-heterocyclic carbon-type ligand coupling in the presence of a base with benzyol halide and styrene coupling partners. These compounds show increased stability for use in the food, cosmetic and pharmaceutical industries.

  本发明涉及一种制备白藜芦醇、白藜芦醇酯和给定以下结构式的取代和未取代的stilbenes的方法；其中每个Y是—O或卤素，每个Z是—O或卤素，每个n和每个m独立地取值为0、1、2、3、4或5，每个A和每个B独立地从Pn、R或缺席中选择，每个V和每个W独立地从Pn、由（2）到（6）个碳原子的直链或支链烷基和由（3）到（8）个碳原子的环烷基、烷氧基、苯基、苄基或卤素中选择，R独立地从包括至少一个碳原子的烷基、芳基和芳基烷基的群体中选择，Pn是醇保护基和上述化合物的对映异构体。这些化合物是通过多步过程制备的，其中包括在碱存在下与苄基卤和苯乙烯偶联合成N-杂环碳型配体偶联。这些化合物在食品、化妆品和制药行业中显示出增强的稳定性。
• Regioselective Lipase-Catalyzed Synthesis of 3-<i>O</i>-Acyl Derivatives of Resveratrol and Study of Their Antioxidant Properties
  作者：Pamela Torres、Ana Poveda、Jesús Jimenez-Barbero、Antonio Ballesteros、Francisco J. Plou

  DOI：10.1021/jf903210q

  日期：2010.1.27

  affording the diester 3,4′-di-O-acetylresveratrol and finally the peracetylated derivative. Long saturated and unsaturated fatty acid vinyl esters were also effective as acyl donors with similar regioselectivity. In contrast, lipase B from Candida antarctica catalyzes the acylation of the phenolic group 4′-OH with 80% yield and negligible formation of higher esters. The analysis of the antioxidant properties

  增加白藜芦醇生物利用度的方法之一是保护其3-OH酚基。在这项工作中，白藜芦醇在3-OH上的区域选择性酰化反应是通过固定化来自Alcaligenes sp。的脂肪酶催化的乙酸乙烯酯的酯交换反应实现的。（脂肪酶QLG）。3- O-乙酰基白藜芦醇的最大产率约为75％，因为脂肪酶还催化其进一步的乙酰化，从而提供二酯3,4'-二-O-乙酰基白藜芦醇，最后得到全乙酰化的衍生物。长的饱和和不饱和脂肪酸乙烯基酯也可以作为酰基给体，具有相似的区域选择性。相反，南极假丝酵母的脂肪酶B催化酚基4'-OH的酰化反应，产率为80％，高级酯的形成可忽略不计。抗氧化剂性能的分析表明，在3-OH处，乙酰基和硬脂酰基衍生物的Trolox等效抗氧化剂能力（TEAC）值分别为白藜芦醇的40％和25％。与在4'-OH位置相比，在3-OH位置添加酰基链导致更高的活性损失。
• Immobilized Lipase Based on Hollow Mesoporous Silicon Spheres for Efficient Enzymatic Synthesis of Resveratrol Ester Derivatives
  作者：Liu-Jia Xu、Tao Yang、Jing Wang、Feng-Hong Huang、Ming-Ming Zheng

  DOI：10.1021/acs.jafc.0c07501

  日期：2021.8.18

  Enzymatic esterification of resveratrol is crucial for its potential application in lipophilic foods and drugs. However, the poor activity of the free enzyme hinders the reaction. In this work, the highly efficient enzymatic synthesis of resveratrol ester derivatives was achieved by immobilized lipase on hydrophobic modified hollow mesoporous silicon spheres (HMSS-C8). We preliminarily explored the

  白藜芦醇的酶促酯化对其在亲脂性食品和药物中的潜在应用至关重要。然而，游离酶的低活性阻碍了反应。在这项工作中，通过将脂肪酶固定在疏水改性中空介孔硅球 (HMSS-C 8 )上，实现了白藜芦醇酯衍生物的高效酶促合成。我们初步探讨了念珠菌的使用。用于白藜芦醇酰化的 99-125 脂肪酶 (CSL)，对 3-OH- 超过 4'-OH-酰化具有区域选择性。HMSS-C 8为 CSL 提供了理想的适应能力，负载能力高达 652 mg/g。CSL@HMSS-C 8的催化效率比游离 CSL 高 15 倍，白藜芦醇的转化率仅在 2 小时内达到 98.7%，是目前文献中记录的最快值。10 个循环后，转化率保持高达 86.3%。受益于更好的脂溶性，含单酯衍生物的油的相对氧化稳定性指数值分别比精制油和含白藜芦醇的油高43.1%~68.8%和23.9%~33.2%。该研究为白藜芦醇酯衍生物的高效酶法合成提供了一条新