4'-acetoxyresveratrol | 411233-11-9

• 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: 4'-acetoxyresveratrol
• 英文别名: 4'-Acetoxy-3,5-dihydroxystilbene；[4-[2-(3,5-dihydroxyphenyl)ethenyl]phenyl] acetate
• CAS: 411233-11-9
• 化学式: C₁₆H₁₄O₄
• 分子量: 270.285
• InChiKey: MEMZFJTYLFBJEC-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

• 作为反应物：
  描述：

  4'-acetoxyresveratrol 在 二叔丁基过氧化物 作用下， 以 苯 为溶剂， 生成
  参考文献：
  名称：

  叔丁氧基从白藜芦醇和两个亲脂性衍生物中提取氢原子。激光闪光光解研究。

  摘要：

  的反应中叔-butoxyl自由基与白藜芦醇（1）和两种乙酰化衍生物（2和3）已通过激光闪光光解 1∶2（v / v）中的技巧 苯–二-叔丁基过氧化在室温下。瞬态吸收光谱叔丁氧基从氢原子夺取H原子时产生的苯氧基酚类已被检测到并已分配。绝对速率常数用于这些反应已被评估为45×10 7，25×10 7 4×10 7中号-1小号-1为1，2和3分别。反应性的顺序1 ≥ 2 » 3已被合理化，在芳环上的乙酰基的位置和作用方面。存在于三个OH基团中白藜芦醇，由于相应的苯氧基自由基通过与环的共轭具有很大的稳定性，因此位置4'的一个反应性最高。但是，在我们的系统中，白藜芦醇事实证明，其在α-生育酚方面逊色于α-生育酚。一个数量级。

  DOI：

  10.1039/b410802g
• 作为产物：
  描述：

  乙酸乙烯酯 、 resveratrol 在 Candida antarctica lipase 作用下， 以 2-甲基-2-丁醇 为溶剂， 反应 10.78h， 生成 4'-acetoxyresveratrol
  参考文献：
  名称：

  Kinetic aspects of ultrasound-accelerated lipase catalyzed acetylation and optimal synthesis of 4′-acetoxyresveratrol

  摘要：

  Ultrasonic assistance of lipase (Candida antarctica; Novozym (R) 435) catalyzed synthesis of 4'-acetoxyresveratrol from resveratrol and vinyl acetate was investigated. Response surface methodology and a three-level-three-factor Box-Behnken design were adopted to evaluate the effects of synthesis variables, including reaction time (4-12 h), enzyme amount (2500-4500 PLU), and ultrasonic power (90-150 W) on the percentage molar conversion of 4'-acetoxyresveratrol. Based on ridge max analysis, the optimum conditions for synthesis were: reaction time 10.78 h, enzyme amount 5492 PLU, and ultrasonic power 147.8 W. With ultrasound assistance, not only the phenolic compound acetylation time decreased, but also a high yield (95.2%) was achieved. The reaction kinetic model agreed with Ping-Pong mechanism, and the apparent kinetic constant V'(m)/K-2 ratio related to enzyme performance was 2.4 times higher in the ultrasound-assisted reaction than in the mechanical-mixing reaction. The apparent kinetic constant K-2 indicated that ultrasound enhanced the vinyl acetate affinity to the enzyme. The simplified Ping-Pong kinetic model was employed to simulate 4'-acetoxyresveratrol production in batch reaction. It was found that a good prediction existed between the fitting results and the experimental data. (c) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ultsonch.2012.05.009

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.

  本发明涉及制备白藜芦醇、白藜芦醇酯和给定公式的取代和未取代的苯乙烯衍生物的方法; 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或不存在中选择，每个V和每个W独立地从(2)到(6)碳原子的直链或支链烷基、(3)到(8)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而成，其中包括在碱的存在下使用苯甲酰卤和苯乙烯偶合物进行N-杂环碳型配体偶合。这些化合物在食品、化妆品和制药工业中具有增强的稳定性。
• 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。
• Methods for Providing Enhanced Resveratrol Activity Using 4-Acetoxy-Resveratrol
  申请人：Lephart Edwin Douglas

  公开号：US20130123357A1

  公开（公告）日：2013-05-16

  The present invention relates to a method of providing enhanced resveratrol activity comprising: administering a therapeutically effective amount of 4-acetoxy-resveratrol for the treatment of and preventing physiological and pathophysiological conditions mediated by (1) sirtuins, (2) estrogen and anti-estrogen hormone actions and (3) chemical interventions important for male and female health, aging, anti-aging and age-related disorders.

  本发明涉及一种提供增强白藜芦醇活性的方法，包括：通过给予治疗有效量的4-乙酰氧基白藜芦醇来治疗和预防由(1)sirtuins、(2)雌激素和抗雌激素激素作用以及(3)对男性和女性健康、衰老、抗衰老和与年龄相关的疾病重要的化学干预介导的生理和病理生理状态。
• Sirtuin activating compounds and processes for making the same
  申请人：Andrus Merritt B.

  公开号：US08841477B2

  公开（公告）日：2014-09-23

  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 Pn, R or absent, each V and each W is independently selected from Pn, 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, Pn 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、白藜芦醇酯和给出的式子中的取代和未取代的苯乙烯衍生物的方法;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独立地选择自Pn、R或不存在，每个V和每个W独立地选择自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，R独立地选择自包括至少一个碳原子的烷基、芳基和芳基烷基的群，Pn是醇保护基和上述化合物的对映异构体。这些化合物通过多步反应制备，包括在碱的存在下与苯乙烯偶联合成苯甲酰卤和苯乙烯偶联配对的N-杂环卡宾型配体偶联。这些化合物在食品、化妆品和制药行业中显示出增加的稳定性。
• Sirtuin activating compounds and methods for making the same
  申请人：Brigham Young University

  公开号：US07714161B2

  公开（公告）日：2010-05-11

  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 Pn, R or absent, each V and each W is independently selected from Pn, 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, Pn 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、白藜芦醇酯和下列公式的取代和未取代的苯乙烯类化合物的方法；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独立地选择自Pn、R或缺失，每个V和每个W独立地选择自Pn、(2)至(6)碳原子的直链或支链烷基和(3)至(8)碳原子的环烷基、烷氧基、苯基、苄基或卤素，R独立地选择自包括至少一个碳原子的烷基、芳基和芳基烷基的群，Pn是醇保护基和上述化合物的对映异构体。这些化合物通过多步过程制备，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。这些化合物在食品、化妆品和制药行业中具有增加的稳定性。