3',4,5'-trihydroxy-4'-geranylstilbene | 117047-35-5

• 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',4,5'-trihydroxy-4'-geranylstilbene
• 英文别名: 4-geranyl-3,5,4'-trihydroxy-trans-stilbene；arachidin 2；4-C-geranyl-resveratrol；2-((E)-3,7-dimethylocta-2,6-dien-1-yl)-5-((E)-4-hydroxystyryl)benzene-1,3-diol；(e)-3,5,4'-Trihydroxy-4-geranylstilbene；2-[(2E)-3,7-dimethylocta-2,6-dienyl]-5-[(E)-2-(4-hydroxyphenyl)ethenyl]benzene-1,3-diol
• CAS: 117047-35-5
• 化学式: C₂₄H₂₈O₃
• 分子量: 364.485
• InChiKey: BBTTUQSLOSGAHM-OBOBVVSZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  60.7
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  硫酸二甲酯 、 3',4,5'-trihydroxy-4'-geranylstilbene 在 potassium carbonate 作用下， 以47 mg的产率得到3',4,5'-trimethoxy-4'-geranylstilbene
  参考文献：
  名称：

  Chlorophora excelsa 的代谢物：五取代二苯乙烯生物发生的可能中间体

  摘要：

  摘要 从优质绿藻心材丙酮提取物中分离并表征了一系列含有取代羟基香叶基芪、取代苯类化合物和槲皮素类黄酮的化合物。

  DOI：

  10.1016/0031-9422(88)80149-3
• 作为产物：
  描述：

  3,4',5-三甲氧基-反-二苯代乙烯 在 吡啶盐酸盐 作用下， 以 乙醇 为溶剂， 反应 2.0h， 生成 3',4,5'-trihydroxy-4'-geranylstilbene
  参考文献：
  名称：

  Chlorophora excelsa 的代谢物：五取代二苯乙烯生物发生的可能中间体

  摘要：

  摘要 从优质绿藻心材丙酮提取物中分离并表征了一系列含有取代羟基香叶基芪、取代苯类化合物和槲皮素类黄酮的化合物。

  DOI：

  10.1016/0031-9422(88)80149-3

文献信息

• [EN] PROCESSES FOR THE PREPARATION OF ORTHO-ALLYLATED HYDROXY ARYL COMPOUNDS<br/>[FR] PROCÉDÉS DE PRÉPARATION DE COMPOSÉS HYDROXY-ARYLE ORTHO-ALLYLÉS
  申请人：UNIV MCMASTER

  公开号：WO2021237371A1

  公开（公告）日：2021-12-02

  The present application describes process for preparing an ortho-allylated hydroxy aryl compounds such as compounds of Formula (I) by reacting an allylic alcohol with a hydroxy aryl compound in the presence of aluminum compound selected from alumina and aluminum alkoxides and in a non-protic solvent wherein at least one carbon atom ortho to the hydroxy group in the hydroxy aryl compound is unsubstituted. The present application also includes compounds of Formula (I).

  本申请描述了一种制备邻烯丙基羟基芳基化合物的方法，例如通过在非质子溶剂中，在氧化铝和铝烷氧化物中选择的铝化合物存在下，将烯丙醇与羟基芳基化合物反应，其中羟基芳基化合物中至少有一个碳原子位于羟基的邻位且未被取代。本申请还包括化合物的化学式（I）。
• Total synthesis and dual PPARα/γ agonist effects of Amorphastilbol and its synthetic derivatives
  作者：Taejung Kim、Woojung Lee、Kyu Hyuk Jeong、Jung Ho Song、Soon-Hye Park、Pilju Choi、Su-Nam Kim、Seokjoon Lee、Jungyeob Ham

  DOI：10.1016/j.bmcl.2012.04.062

  日期：2012.6

  extract, is a biologically interesting natural trans-stilbene compound with dual peroxisome proliferator-activated receptor (PPAR) α/γ agonist activity. After total synthesis of APH-1 and its derivatives by Pd-catalyzed Suzuki–Miyaura cross-coupling of a common (E)-styryl bromide intermediate and various aromatic trifluoroborate compounds, we biologically evaluated APH-2–APH-12 for PPAR agonist activity

  Amorphastilbol（APH-1），从刺槐变种中分离。伞菌种子提取物，是一种生物学上有趣的天然反式二苯乙烯化合物，具有双重过氧化物酶体增殖物激活受体（PPAR）α/γ激动剂活性。一个共同的后通过Pd催化的铃木-宫浦APH-1及其衍生物的总合成的交叉偶联（É）-苯乙烯基溴化物中间体和各种芳族三氟硼酸盐化合物，我们对APH-2–APH-12的PPAR激动剂活性进行了生物学评估。与APH-1相比，APH-4和APH-11是有效的PPARα/γ转录激活因子。因此，我们建议APH-4和APH-11是新型的双重PPARα/γ激动剂，并可能通过增强葡萄糖和脂质代谢来治疗2型糖尿病。
• Heterologous biosynthesis of prenylated resveratrol and evaluation of antioxidant activity
  作者：Shengtao Bo、Sui Kiat Chang、Ting Zhou、Hong Zhu、Yueming Jiang、Bao Yang

  DOI：10.1016/j.foodchem.2022.132118

  日期：2022.6

  Prenylated stilbenoids are good candidates of nutraceuticals presented in food resources. The levels of natural prenylated stilbenoids are usually low. Biotransformation is a promising synthesis strategy to produce novel bioactive compounds. However, information regarding biosynthesis of prenylated stilbenoids is rare. In this work, prenyltransferase and geranyl diphosphate biosynthesis pathway were

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• Catalytic prenylation of natural polyphenols
  作者：Yi Du、Iman Korchi、Aleksandr E. Rubtsov、Andrei V. Malkov

  DOI：10.1039/d3nj04371a

  日期：——

  Prenylated polyphenols occur naturally and exhibit biological activity superior to the ubiquitous parent polyphenols. However, their low abundance limits the wider application of these derivatives. In this work, we present an expedient, single-step catalytic protocol for introducing terpene fragments into the aromatic rings of the widely available natural stilbenoids and flavonoids to upgrade their

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• Chemoenzymatic syntheses of prenylated aromatic small molecules using Streptomyces prenyltransferases with relaxed substrate specificities
  作者：Takuto Kumano、Stéphane B. Richard、Joseph P. Noel、Makoto Nishiyama、Tomohisa Kuzuyama

  DOI：10.1016/j.bmc.2008.07.052

  日期：2008.9

  NphB is a soluble prenyltransferase from Streptomyces sp. strain CL190 that attaches a geranyl group to a 1,3,6,8-tetrahydroxynaphthalene-derived polyketide during the biosynthesis of anti-oxidant naphterpin. Here we report multiple chemoenzymatic syntheses of various prenylated compounds from aromatic substrates including flavonoids using two prenyltransferases NphB and SCO7190, a NphB homolog from Streptomyces coelicolor A3( 2), as biocatalysts. NphB catalyzes carbon-carbon-based and carbon-oxygen-based geranylation of a diverse collection of hydroxyl-containing aromatic acceptors. Thus, this simple method using the prenyltransferases can be used to explore novel prenylated aromatic compounds with biological activities. Kinetic studies with NphB reveal that the prenylation reaction follows a sequential ordered mechanism. (C) 2008 Elsevier Ltd. All rights reserved.