3-O-acetylresveratrol

• 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: 3-O-acetylresveratrol
• 英文别名: [3-Hydroxy-5-[2-(4-hydroxyphenyl)ethenyl]phenyl] acetate
• 化学式: C₁₆H₁₄O₄
• 分子量: 270.285
• InChiKey: FATXNQWLANBPPI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3,5,4'-tri-O-acetylresveratrol 、 resveratrol 在 potassium carbonate 作用下， 以 二甲基亚砜 为溶剂， 反应 2.0h， 以76%的产率得到3,5-di-O-acetylresveratrol
  参考文献：
  名称：

  利用固有亲核试剂通过分子间合作酯交换反应进行多酚的区域选择性O酰化

  摘要：

  已经开发了一种绿色有效的多酚区域选择性O-酰化方法。可以在温和条件下通过分子间合作酯交换利用“固有亲核试剂”，在碳酸钾/二甲亚砜体系中进行酰化反应。该方法在带有2'，4'-二羟基苯乙酮部分的多酚的区域选择性酰化中显示出特别的优势，并且可以扩展为不具有该部分的多酚的单乙酸酯或多种乙酸酯的合成。与其他已报道的方法相比，该方法具有原子经济性，并且在避免使用任何金属基催化剂方面更加环保。

  DOI：

  10.1016/j.tet.2016.05.048

文献信息

• 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。
• Compositions for manipulating the lifespan and stress response of cells and organisms
  申请人：Howitz T. Konrad

  公开号：US20060084135A1

  公开（公告）日：2006-04-20

  Provided herein are methods and compositions for modulating the activity of sirtuin deacetylase protein family members; p53 activity; apoptosis; lifespan and sensitivity to stress of cells and organisms. Exemplary methods comprise contacting a cell with an activating compound, such as a flavone, stilbene, flavanone, isoflavone, catechin, chalcone, tannin or anthocyanidin; or an inhibitory compound, such as a sphingolipid, e.g., sphingosine.

  本文提供了一种调节sirtuin去乙酰化酶蛋白家族成员、p53活性、细胞和生物的凋亡、寿命和对压力敏感性的方法和组合物。其中一种示例方法包括使用活化化合物（如黄酮、双苯乙烯、黄烷酮、异黄酮、儿茶素、查尔酮、单宁或花青素）或抑制化合物（如鞘脂类化合物，例如鞘氨醇）与细胞接触。
• NOVEL SIRTUIN ACTIVATING COMPOUNDS AND PROCESSES FOR MAKING THE SAME
  申请人：Andrus Merritt B.

  公开号：US20100185006A1

  公开（公告）日：2010-07-22

  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 carbene-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.

  本发明涉及制备白藜芦醇、白藜芦醇酯和给出下列式子的取代和未取代的苯乙烯的方法；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是独立地取值为0、1、2、3、4或5，每个A和每个B是独立地从Pn、R或缺失中选择，每个V和每个W是独立地从Pn、2到6个碳原子的直链或支链烷基和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是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反应制备的，包括在碱存在下与苯乙烯偶联反应的N-杂环卡宾型配体偶联反应。这些化合物表现出增强的稳定性，可用于食品、化妆品和制药工业中。
• SIRT1 modulators for manipulating cell/organism lifespan/stress response
  申请人：President and Fellows of Harvard College

  公开号：EP2289504A2

  公开（公告）日：2011-03-02

  Provided herein are methods and compositions for modulating the activity of sirtuin deacetylase protein family members; p53 activity; apoptosis; lifespan and sensitivity to stress of cells and organisms. Exemplary methods comprise contacting a cell with an activating compound, such as a flavone, stilbene, flavanone, isoflavone, catechin, chalcone, tannin or anthocyanidin; or an inhibitory compound, such as a sphingolipid, e.g., sphingosine.

  本文提供了用于调节 sirtuin 去乙酰化酶家族成员活性、p53 活性、细胞凋亡、寿命以及细胞和生物体对应激的敏感性的方法和组合物。示例性方法包括使细胞与激活化合物接触，如黄酮、链烯、黄烷酮、异黄酮、儿茶素、查尔酮、单宁或花青素；或与抑制化合物接触，如鞘磷脂，如鞘磷脂。
• Formulation and process for modulating wound healing
  申请人：BioMendics, LLC

  公开号：US10426742B2

  公开（公告）日：2019-10-01

  Methods and compounds are disclosed for wound healing by modulating autophagy. A formulation for modulating autophagy comprises a first modulating compound (FAM) selected from compounds having the general structure (I): wherein: L represents a linker selected from —C≡C—, (a tolan), —CH═CH— (a stilbene, preferably trans); or —CRa═CRb— a stilbene derivative; where Ra and Rb are independently H or phenyl optionally substituted with —(R3)p or —(R4)q; R1 to R4 are independent substituents at any available position of the phenyl rings, preferably at 3, 3′, 4, 4′, and/or 5, 5′; and m, n, p, and q are independently 0, 1, 2, or 3 representing the number of substituents of the rings, respectively, but at least one of m or n must be ≥1. Each R1 to R2 is independently selected from substituents described herein, including but not limited to hydroxyl, alkoxy, halo, halomethyl and glycosides. The formulation may also include an auxiliary autophagy modulating compound (AAM) as described herein. The formulation may include a hydrogel formed by the compounds themselves or otherwise and may include salts and/or complexes.

  本发明公开了通过调节自噬促进伤口愈合的方法和化合物。用于调节自噬的制剂包括选自具有一般结构 (I) 的化合物的第一调节化合物 (FAM)： 其中L 代表选自-C≡C-（甲苯）、-CH═CH-（二苯乙烯，最好是反式）或-CRa═CRb-二苯乙烯衍生物的连接体；其中 Ra 和 Rb 独立地是 H 或任选被-(R3)p 或-(R4)q 取代的苯基； R1至R4是独立的取代基，位于苯基环的任何可用位置，优选位于3，3′、4，4′和/或5，5′；m、n、p和q分别独立地为0、1、2或3，代表环的取代基数目，但m或n中至少有一个必须≥1。每个 R1 至 R2 独立地选自本文所述的取代基，包括但不限于羟基、烷氧基、卤代、卤代甲基和苷。制剂还可包括本文所述的辅助自噬调节化合物（AAM）。制剂可包括由化合物本身或以其它方式形成的水凝胶，并可包括盐和/或复合物。