(-)-5-(3',4',5'-Trihydroxyphenyl)-γ-valerolactone

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: (-)-5-(3',4',5'-Trihydroxyphenyl)-γ-valerolactone
• 英文别名: 5-(3′,4′,5′-trihydroxyphenyl)-γ-valerolactone；5-(3',4',5'-Trihydroxyphenyl)-gamma-valerolactone；5-[(3,4,5-trihydroxyphenyl)methyl]oxolan-2-one
• 化学式: C₁₁H₁₂O₅
• 分子量: 224.213
• InChiKey: CZVAQLJEUUFQCH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  87
• 氢给体数：
  3
• 氢受体数：
  5

ADMET

代谢

5-(3p,4p,5p-三羟基苯基)-γ-戊内酯已知的人类代谢物包括5-(3',4',5'-三羟基苯基)-γ-戊内酯-3'-O-葡萄糖苷酸。

5-(3p,4p,5p-Trihydroxyphenyl)-gamma-valerolactone has known human metabolites that include 5-(3',4',5'-Trihydroxyphenyl)-gamma-valerolactone-3'-O-glucuronide.

来源:NORMAN Suspect List Exchange

反应信息

• 作为产物：
  描述：

  1-(3,4,5-trimethoxyphenyl)prop-2-en-1-ol 在 palladium on activated charcoal 氢氧化钾 、 氢气 、 三溴化硼 、 sodium carbonate 、 copper(II) sulfate 、 丙酸 、 间氯过氧苯甲酸 作用下， 以 甲醇 、 二氯甲烷 、 苯 为溶剂， 生成 (-)-5-(3',4',5'-Trihydroxyphenyl)-γ-valerolactone
  参考文献：
  名称：

  Synthesis and biological activity of the tea catechin metabolites, M4 and M6 and their methoxy-derivatives

  摘要：

  Syntheses are reported for metabolites M4 (1) and M6 (2) of the green tea polyphenols epicatechin (EC) and epigallocatechin (EGC) and their gallate derivatives. Several methoxy-derivatives of 1 and 2 were also prepared. Compounds 1 and 2 were evaluated for growth inhibitory activity against a panel of immortalized and malignant human cell lines with 1 being the more active compound. The possible antiinflammatory activity of 1 and its trimethoxy derivative was also evaluated. Neither compound inhibited the release of arachidonic acid, although 1 inhibited NO production by 50% at 20 muM. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.12.070

文献信息

• Metabolism of (−)-Epigallocatechin Gallate by Rat Intestinal Flora
  作者：Akiko Takagaki、Fumio Nanjo

  DOI：10.1021/jf903375s

  日期：2010.1.27

  5′-trihydroxyphenyl)-3-(2′′,4′′,6′′-trihydroxyphenyl)propan-2-ol (3) by reductive cleavage between 1 and 2 positions of EGC, and subsequently metabolite 3 was converted to 1-(3′,5′-dihydroxyphenyl)-3-(2′′,4′′,6′′-trihydroxyphenyl)propan-2-ol (4) followed by the conversion to 5-(3,5-dihydroxyphenyl)-4-hydroxyvaleric acid (5) by decomposition of the phloroglucinol ring in metabolite 4. This degradation pathway

  体外研究了大鼠肠道细菌对（-）-表没食子儿茶素没食子酸酯（EGCg）的厌氧代谢。首先，用169株肠细菌筛选出能够将EGCg水解为（-）-表没食子儿茶素（EGC）和没食子酸（2）的肠细菌。结果，产生了产气肠杆菌，植物拉乌尔氏菌，肺炎克雷伯菌。肺炎和长双歧杆菌亚种。发现婴儿可以水解EGCg。EGCg代谢的后续步骤是EGC的降解（1）被肠道细菌感染。然后，将EGC与大鼠肠道细菌在0.1 M磷酸盐缓冲液（pH 7.1）中温育，并通过HPLC或LC-MS对降解产物进行时间分析。此外，由EGC形成的产物被分离并通过LC-MS和NMR分析鉴定。结果表明，EGC首先通过以下方法转化为1-（3'，4'，5'-三羟基苯基）-3-（2''，4''，6''-三羟基苯基）丙-2-醇（3）在EGC的1和2位之间进行还原性裂解，随后将代谢物3转化为1-（3'，5'-二羟基苯基）-3-（2''，4''，6''-三羟基苯基）丙烷-2-
• Catalytic, Enantioselective Vinylogous Mukaiyama Aldol Reaction of Furan-Based Dienoxy Silanes: A Chemodivergent Approach to γ-Valerolactone Flavan-3-ol Metabolites and δ-Lactone Analogues
  作者：Claudio Curti、Nicoletta Brindani、Lucia Battistini、Andrea Sartori、Giorgio Pelosi、Pedro Mena、Furio Brighenti、Franca Zanardi、Daniele Del Rio

  DOI：10.1002/adsc.201500705

  日期：2015.12.14

  a set of hydroxyphenyl γ-valerolactones was achieved starting from 2-silyloxyfuran and alkoxy-substituted benzaldehydes as common precursors. Key synthesis steps included an enantioselective vinylogous Mukaiyama aldol reaction and a Barton–McCombie deoxygenation. Five enantioenriched γ-valerolactone targets were obtained in 5–6 steps, 18–63% overall yields and 82–98 % ee, paving the way for the straightforward

  从2-甲硅烷氧基呋喃和烷氧基取代的苯甲醛作为常见的前体开始，实现了一组羟苯基γ-戊内酯的不对称合成。关键的合成步骤包括对映选择性的乙烯基Mukaiyama aldol反应和Barton-McCombie脱氧反应。通过5–6个步骤获得了5个对映体富集的γ-戊内酯目标，总产率为18–63％，ee为82–98％，这为直接进入此类具有生物有效性且难得的flavan -3-ol代谢物铺平了道路。同时，偶然发现了一种空前的一锅还原环扩展过程，从酚丁醇化物前体产生外消旋的δ-内酯类似物。
• Ligand‐Enabled Ni^II‐Catalyzed Hydroxylarylation of Alkenes with Molecular Oxygen
  作者：Dao‐Ming Wang、Li‐Qin She、Hao Yuan、Yichen Wu、Yong Tang、Peng Wang

  DOI：10.1002/anie.202304573

  日期：2023.8.28

  The use of molecular oxygen as the terminal oxidant in transition metal catalyzed oxidative process is an appealing and challenging task in organic synthetic chemistry. Here, we report a Ni‐catalyzed hydroxylarylation of unactivated alkenes enabled by a β‐diketone ligand with high efficiency and excellent regioselectivity employing molecular oxygen as the oxidant and hydroxyl source. This reaction features mild conditions, broad substrate scope and incredible heterocycle compatibility, providing a variety of β‐hydroxylamides, γ‐hydroxylamides, β‐aminoalcohols, γ‐aminoalcohols, and 1,3‐diols in high yields. The synthetic value of this methodology was demonstrated by the efficient synthesis of two bioactive compounds, (±)‐3′‐methoxyl citreochlorol and tea catechin metabolites M4.

  摘要在过渡金属催化的氧化过程中使用分子氧作为末端氧化剂是有机合成化学中一项既吸引人又具有挑战性的任务。在此，我们报告了一种镍催化的未活化烯烃羟基芳基化反应，该反应以分子氧为氧化剂和羟基源，由β-二酮配体促成，具有高效率和优异的区域选择性。该反应具有条件温和、底物范围广、杂环兼容性强等特点，能以高产率提供各种 β-羟基酰胺、γ-羟基酰胺、β-氨基醇、γ-氨基醇和 1,3-二醇。(±)-3′-methoxyl citreochlorol 和茶儿茶素代谢物 M4 这两种生物活性化合物的高效合成证明了该方法的合成价值。
• GLYCAN THERAPEUTICS AND RELATED METHODS THEREOF
  申请人：Kaleido Biosciences, Inc.

  公开号：EP3354282A1

  公开（公告）日：2018-08-01

  Preparations of glycan therapeutics, pharmaceutical compositions and medical foods thereof, optionally comprising micronutrients, polyphenols, prebiotics, probiotics, or other agents are provided and methods of making same. Also provided are methods of using said gycan therapeutics, e.g. for the modulation of human gastrointestinal microbiota and to treat dysbioses.

  本发明提供了可选择包含微量营养素、多酚、益生元、益生菌或其他制剂的聚糖疗法制剂、药物组合物及其医用食品，以及制造方法。还提供了使用所述糖治疗剂的方法，例如用于调节人类胃肠道微生物群和治疗菌群失调。
• METHOD FOR TREATING A SUBTERRANEAN FORMATION
  申请人：Schlumberger Technology Corporation

  公开号：US20160289544A1

  公开（公告）日：2016-10-06

  A method of treating a subterranean formation including combining an aqueous fluid, a biomaterial, an enzyme, and a deactivator to form a treatment fluid; and introducing the treatment fluid into the subterranean formation. A method is also disclosed for treating a subterranean formation by preparing a treatment fluid containing an aqueous fluid that contains bacterial and/or fungal cells that produce an enzyme that degrades the biomaterial, a biomaterial, and a deactivator; controlling degradation of the biomaterial by adding an effective amount of the deactivator to the aqueous fluid prior to the preparation of the treatment fluid; and introducing the treatment fluid into the subterranean formation. In the methods, the enzyme degrades the biomaterial and the deactivator is an oxygen-containing arene capable of inhibiting the enzyme from degrading the biomaterial.