3-O-butanoyl resveratrol

• 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-butanoyl resveratrol
• 英文别名: 3-O-butanoylresveratro1；[3-hydroxy-5-[(E)-2-(4-hydroxyphenyl)ethenyl]phenyl] butanoate
• 化学式: C₁₈H₁₈O₄
• 分子量: 298.339
• InChiKey: AFGTZEQRYHMOAN-SNAWJCMRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 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：

  白藜芦醇 在 吡啶 、 Candida antarctica lipase 作用下， 以 正丁醇 为溶剂， 反应 48.0h， 生成 3-O-butanoyl resveratrol
  参考文献：
  名称：

  Chemo-enzymatic synthesis and cell-growth inhibition activity of resveratrol analogues

  摘要：

  The stilbenoid resveratrol (1) was subjected to regioselective acetylation catalysed by Candida antarctica lipase (CAL) to obtain 4'-acetylresveratrol (2). CAL biocatalysed regioselective alcoholysis of 3,5,4'-triacetylresveratrol (3), 3,5,4'-tributanoylresveratrol (6), and 3, 4, 5'-trioctanoylresveratrol (9) afforded derivatives 4, 5, 7, 8, 10, and 11. Further resveratrol analogues (12-18) were obtained through methylation and hydrogenation reactions, whereas the 3,4,4'-trimethoxystilbene (19) was obtained by complete synthesis. Resveratrol and its lipophylic analogues were subjected to cell-growth inhibition bioassays towards DU-145 human prostate cancer cells. Compounds 2-19 showed cell-growth inhibition activity comparable to or higher than resveratrol (GI(50) = 24.09 muM), displaying low or very low toxicity against non-tumorigenic human fibroblast cells. Comparison of the trimethoxy stilbenes 12 (GI(50) = 2.92 muM) and 19 (GI(50) = 25.39 muM) indicates that the position of the substituents is important for the activity. The marked activity of methyl ethers 12, 13, and 18 in comparison with that of the corresponding esters suggests that the different chemical reactivity, rather than steric factors, strongly influences the activity.(C) 2004 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.bioorg.2004.08.003

文献信息

• Separation and Identification of Resveratrol Butyrate Ester Complexes and Their Bioactivity in HepG2 Cell Models
  作者：Ming-Kuei Shih、You-Lin Tain、Chiu-Min Cheng、Chien-Ning Hsu、Yu-Wei Chen、Hung-Tse Huang、Chi-I Chang、Chih-Yao Hou

  DOI：10.3390/ijms222413539

  日期：——

  capacity and anti-fat accumulation activity in previous studies. In this study, silica gel, high-performance liquid chromatography, and 1H nuclear magnetic resonance were used for separation and identification of RBE complex components. With the exception of resveratrol, five different structures of ester derivatives were separated from silica gel: 3,4′-di-O-butanoylresveratrol (ED2, 18.8%), 3-O-butanoylresveratrol

  在先前的研究中，白藜芦醇丁酸酯 (RBE) 复合物已表现出更高的抗氧化能力和抗脂肪积累活性。本研究采用硅胶、高效液相色谱、1H核磁共振等方法对RBE复合物组分进行分离鉴定。除白藜芦醇外，从硅胶中分离出五种不同结构的酯衍生物：3,4'-二-O-丁酰白藜芦醇（ED2, 18.8%）、3-O-丁酰白藜芦醇（ED4, 35.7%）、4'- O-丁酰白藜芦醇 (ED5, 4.4%)、3,5,4'-三-O-丁酰白藜芦醇 (ED6, 1.5%) 和 3,5-二-O-丁酰白藜芦醇 (ED7, 0.7%)。在获得的酯衍生物中，ED2 和 ED4 是 RBE 复合物中的主要酯衍生物。因此，评估了 RBE 混合物、ED2 和 ED4 的细胞抗氧化活性。结果表明，ED2和ED4的抗氧化能力高于RBE混合物，表明丁酸酯化位点的数量和位置与细胞存活率和抗氧化能力有关。本研究首次报道了 RBE 复合物衍生物的成功分离、结构鉴定和细胞生物抗氧化活性，这是
• Lipophilization of Resveratrol and Effects on Antioxidant Activities
  作者：Won Young Oh、Fereidoon Shahidi

  DOI：10.1021/acs.jafc.7b03129

  日期：2017.10.4

  lipophilicity of resveratrol and its alkyl esters was calculated using ALOGPS 2.1. Resveratrol exhibited greater antioxidant activity in both 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical and 2,2′-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS) radical cation scavenging assays. Resveratrol esters with long-chain fatty acids (C18:0 and C18:1) showed higher antioxidant activity in the DPPH radical scavenging

  白藜芦醇（R）是一种多酚，通过与选定脂肪酸的酯化反应进行结构改性，以扩大其在亲脂性食品，药物和化妆品中的潜在应用。酯化反应使用12种不同的脂肪酸，具有不同的链长和不饱和度（C3：0–C22：6）。通过高效液相色谱-质谱法鉴定了两个单酯，两个二酯和一个三酯，以及单酯（R-3- O-单二十二碳六烯酸酯和R-4'- O-单十二碳六烯酸酯）在结构上通过核磁共振证实。白藜芦醇及其烷基酯的亲脂性是使用ALOGPS 2.1计算的。白藜芦醇在2,2-二苯基-1-吡啶并肼基（DPPH）和2,2'-叠氮基双（3-乙基苯并噻唑啉-6-磺酸）（ABTS）自由基阳离子清除试验中均显示出更高的抗氧化活性。在DPPH自由基清除试验中，具有长链脂肪酸（C18：0和C18：1）的白藜芦醇酯显示出更高的抗氧化活性，而短链脂肪酸（C3：0，C4：0和C6：0）显示出更高的抗氧化活性。 ABTS自由基阳离子清除测定中的抗氧化剂活
• Emulsion Cosmetic Compositions Containing Resveratrol Derivatives And Linear Or Branched Silicone
  申请人：Maes Daniel H.

  公开号：US20090035242A1

  公开（公告）日：2009-02-05

  An emulsion cosmetic composition comprising at least one resveratrol derivative, a water phase, and an oil phase containing at least one linear or branched volatile or near volatile silicone and a method for delivering active resveratrol to the skin.

  一种乳液化妆品组合物，包括至少一种白藜芦醇衍生物、水相和油相，其中油相包含至少一种线性或支链挥发性或准挥发性硅氧烷，并且提供一种向皮肤传递活性白藜芦醇的方法。
• Anhydrous Cosmetic Compositions Containing Resveratrol Derivatives
  申请人：Czarnota Anna

  公开号：US20090035243A1

  公开（公告）日：2009-02-05

  An anhydrous color cosmetic composition comprising at least one resveratrol derivative and particulates; and an anhydrous emulsion skin care composition.

  一种无水色彩化妆品组合物，包括至少一种白藜芦醇衍生物和粒状物质；以及一种无水乳化皮肤护理组合物。
• Emulsion Cosmetic Compositions Containing Resveratrol Derivatives And An Oil Phase Structuring Agent
  申请人：Maes Daniel H.

  公开号：US20090035236A1

  公开（公告）日：2009-02-05

  An emulsion cosmetic composition comprising at least one resveratrol derivative, an aqueous phase, and an oil phase having at and at least one oil phase structuring agent, and a method for preparing emulsions capable of delivering active resveratrol to the skin.

  一种乳液化妆品组合物，包括至少一种白藜芦醇衍生物、水相、油相和至少一种油相结构调节剂，并提供了一种制备乳液，能够将活性白藜芦醇输送到皮肤的方法。