3-O-dodecanoyl-(+)-catechin

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: 3-O-dodecanoyl-(+)-catechin
• 英文别名: 3-lauroyl-(+)-catechin；[(2R,3S)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3,4-dihydro-2H-chromen-3-yl] dodecanoate
• 化学式: C₂₇H₃₆O₇
• 分子量: 472.579
• InChiKey: KOSUCDKDCCNEII-AHKZPQOWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  34
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  116
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  3',4',3,5,7-pentadodecanoyl (+)-catechin 在 肼 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 8.0h， 以75%的产率得到3-O-dodecanoyl-(+)-catechin
  参考文献：
  名称：

  Targeted acylation for all the hydroxyls of (+)-catechin and evaluation of their individual contribution to radical scavenging activity

  摘要：

  The reactivity profile of all the hydroxyl groups in (+)-catechin towards acylation and their respective contribution to radical scavenging activity were systematically explored in this work. Selective acylation of the hydroxyls on different rings was carried out employing either a basic or acidic activation strategy. Monoacylation of B ring was achieved effectively with the aid of dimethyltin dichloride. Monoacylation of A ring was accomplished by sequential protection and deprotection of B and C rings. Based on specific acylation of all the individual hydroxyls of (+)-catechins, the structure radical scavenging activity relationship of each hydroxyl of (+)-catechin was established. It was demonstrated that the vicinal phenolic hydroxyls on B ring played the most important role in the ABTS radical scavenging activity and those on A and C rings made a much smaller contribution. This study has laid solid groundwork for further modification of the catechins and improvement of their properties.

  DOI：

  10.1016/j.foodchem.2015.10.134

文献信息

• Antimicrobial Activity of 3-<i>O</i>-Acyl-(-)-epicatechin and 3-<i>O</i>-Acyl-(+)-catechin derivatives
  作者：Park, Ki Duk、Park, Yoon Sun、Cho, Sung Jin、Sun, Won Suck、Kim, Sung Han、Jung, Do Hyun、Kim, Jung Han

  DOI：10.1055/s-2004-818923

  日期：2004.3

  compounds, 3- O-acyl-(-)-epicatechins and 3- O-acyl-(+)-catechins possessing various aromatic groups and aliphatic chains of varying length from C4 to C16 for increasing lipophilicity were synthesized and tested for antimicrobial activities against Gram-positive, Gram-negative bacteria and fungi. The (-)-epicatechin and (+)-catechin derivatives comprised of aromatic groups increased activity and derivatives

  作为抗菌促进化合物的探索性研究，3-O-酰基-（-）-表儿茶素和3-O-酰基-（+）-儿茶素具有不同的芳香族基团和从C4到C16的不同长度的脂族链，以增加亲脂性。合成并测试了对革兰氏阳性，革兰氏阴性细菌和真菌的抗菌活性。由芳族基团组成的（-）-表儿茶素和（+）-儿茶素衍生物的活性增强，并且在C8至C10的附近具有碳原子酰基链基的衍生物表现出很强的抗菌活性（MIC = 2-8 microg / ml）抵抗革兰氏阳性细菌，抗真菌活性弱。然而，当取代基的碳链长度太短（C4至C6）或太长（C16）时，活性降低。
• Synthesis of Lipophilic Poly-Lauroyl-(+)-Catechins and Radical-Scavenging Activity
  作者：Guangzhi JIN、Hisashi YOSHIOKA

  DOI：10.1271/bbb.69.440

  日期：2005.1

  Lipophilic catechins were synthesized to improve absorption into living bodies and obtain new antioxidants effective in lipid bilayers. The hydroxyl (OH) groups of (+)-catechin was acylated randomly using lauroyl chloride. The mixture was separated by preparative HPLC, and 3-lauroyl-, 3′,4′-dilauroyl- and 3,3′,4′-trilauroyl-catechins (3-LC, 3′,4′-LC, and 3,3′,4′-LC) were obtained, their structures being determined by 1H NMR. Their radical scavenging activity was measured in a ethanol solution using the 1,1-diphenyl-2-picrylhydrazyl radical, and was compared with that of (+)-catechin. The activity of 3-LC was almost same as that of (+)-catechin, but those of 3′,4′-LC and 3,3′,4′-LC were small, showing that the blocking of phenolic OH groups in the B ring lowered the activity. The scavenging activity on lipophilic radicals in a liposome system was also measured, and the activities were in the order of 3-LC > 3′,4′-LC = (+)-catechin. These results suggested that radical scavenging activity in the lipid membrane depended not only on the number and the relative positions of phenolic OH groups of catechins but also on affinity to the membrane.

  合成亲脂性儿茶素的目的是提高活体吸收率，并获得在脂质双分子层中有效的新型抗氧化剂。用月桂酰氯随机酰化(+)-儿茶素的羟基（OH）。混合物经制备型高效液相色谱分离，得到 3-月桂酰基、3′,4′-二月桂酰基和 3,3′,4′-三月桂酰基儿茶素（3-LC、3′,4′-LC 和 3,3′,4′-LC），并通过 1H NMR 确定了它们的结构。在乙醇溶液中用 1,1-二苯基-2-苦基肼自由基测定了它们的自由基清除活性，并与(+)-儿茶素的自由基清除活性进行了比较。3-LC的活性与(+)-儿茶素基本相同，但3′,4′-LC和3,3′,4′-LC的活性较小，这表明B环中的酚羟基受阻降低了活性。此外，还测定了脂质体系统中的亲脂自由基清除活性，其顺序为 3-LC > 3′,4′-LC=（+）-儿茶素。这些结果表明，儿茶素在脂膜中的自由基清除活性不仅取决于酚羟基的数量和相对位置，还取决于与膜的亲和性。
• Inhibitory Effects of 3-O-Acyl-(+)-catechins on Epstein-Barr Virus Activation
  作者：Shinichi Uesato、Keisuke Taniuchi、Ayako Kumagai、Yasuo Nagaoka、Ryota Seto、Yukihiko Hara、Harukuni Tokuda、Hoyoku Nishino

  DOI：10.1248/cpb.51.1448

  日期：——

  exploratory investigation of antitumor-promoting catechins, 3-O-acyl-(+)-catechins of varying carbon lengths from C(4) to C(18) were assessed for inhibitory effects on the activation of the Epstein-Barr virus early antigen. Like 3-O-acyl-(-)-epigallocatechins, the (+)-catechin derivatives showed promising effects with the C-3 acyl chain of C(8)-C(11) carbon atoms.

  在对促进肿瘤的儿茶素进行探索性研究的过程中，评估了碳长度从C（4）到C（18）的3-O-酰基-（+）-儿茶素对Epstein-活化的抑制作用巴尔病毒早期抗原。像3-O-酰基-（-）-表没食子儿茶素一样，（+）-儿茶素衍生物在C（8）-C（11）碳原子的C-3酰基链上显示出可喜的效果。
• [EN] ANTIMICROBIAL COMPOSITIONS AND METHODS OF USE<br/>[FR] COMPOSITIONS ANTIMICROBIENNES ET PROCEDES D'UTILISATION
  申请人：STAPLETON PAUL

  公开号：WO2005034976A1

  公开（公告）日：2005-04-21

  A catechin is modified in at least one position (most preferably in the 3-position of the C-ring) to increase its lipophilicity. Contemplated catechins are demonstrated to have significantly improved antibacterial properties, likely due to catastrophic membrane damage.

  一种儿茶素至少在一个位置上进行改变（最好是在C环的3号位置）以增加其亲脂性。考虑到的儿茶素已被证明具有显著改善的抗菌性能，可能是由于破坏细胞膜所致。
• ANTIMICROBIAL COMPOSITIONS AND METHODS OF USE
  申请人：Stapleton, Paul

  公开号：EP1663124A1

  公开（公告）日：2006-06-07