3-(8-hydroxyoctyl)phenol

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 3-(8-hydroxyoctyl)phenol
• 英文别名: 8-(3-hydroxyphenyl)octan-1-ol
• 化学式: C₁₄H₂₂O₂
• 分子量: 222.327
• InChiKey: SLVFVSVYCYGPJP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  16
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(8-hydroxyoctyl)phenol 在 Jones reagent 、 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 24.08h， 生成 8-(3-methoxyphenyl)octanoic acid
  参考文献：
  名称：

  [EN] PPAR MODULATORS
  [FR] MODULATEURS DE PPAR

  摘要：

  本申请涉及amorfrutin类似物的使用作为PPAR调节剂，用于治疗代谢综合征、肥胖症、高脂血症、空腹高血糖、高血压、低HDL胆固醇、2型糖尿病、心血管疾病、神经退行性疾病、疟疾或肠易激综合征。

  公开号：

  WO2015176153A1
• 作为产物：
  描述：

  8-(3-hydroxyphenyl)octanal 在 sodium tetrahydroborate 作用下， 以 甲醇 、 水 为溶剂， 反应 4.0h， 生成 3-(8-hydroxyoctyl)phenol
  参考文献：
  名称：

  西洋参（Anacardium occidentale）（腰果）中酚类的臭氧化作用

  摘要：

  AbstractThe phenolic lipid components cardanol and cardol, obtained from heat‐processed technical cashew nutshell liquid from Anacardium occidentale, and anacardic acid from the natural product, each containing monoene, diene, and triene constituents, were ozonized. The ozonides were reduced chemically and catalytically to give 8‐(3‐hydroxyphenyl)octanal, 8‐(3,5‐dihydroxyphenyl)octanal, and 8‐(3‐hydroxy‐2‐carboxyphenyl)octanal, respectively, together with formaldehyde, malondialdehyde, butanal, and heptanal in each case. Reduction of the 8‐(3‐hydroxyphenyl)octanal, which was synthesized from 3‐benzyloxybenzaldehyde, gave 3‐octylphenol. Oxidation of the aldehyde with potassium permanganate gave 8‐(3‐hydroxyphenyl)octanoic acid, and reduction with sodium borohydride yielded 8‐(3‐hydroxyphenyl)octanol. For comparison, the trans‐diols of cardanol were prepared by treatment of cardanol with peroxyformic acid and cleaved by periodate oxidation to give an alternative route to 8‐(3‐hydroxyphenyl)octanal but in lower yield. Likewise, the cis‐diols were obtained with potassium permanganate and cleaved without isolation to give the same product in lower yield compared with ozonization.

  DOI：

  10.1007/s11746-002-0549-8

文献信息

• Discovery of Sustainable Drugs for Neglected Tropical Diseases: Cashew Nut Shell Liquid (CNSL)‐Based Hybrids Target Mitochondrial Function and ATP Production in <i>Trypanosoma brucei</i>
  作者：Michela Cerone、Elisa Uliassi、Federica Prati、Godwin U. Ebiloma、Leandro Lemgruber、Christian Bergamini、David G. Watson、Thais de A. M. Ferreira、Gabriella Simões Heyn Roth Cardoso、Luiz A. Soares Romeiro、Harry P. de Koning、Maria Laura Bolognesi

  DOI：10.1002/cmdc.201800790

  日期：2019.3.22

  African trypanosomiasis (HAT), we developed hybrid compounds by merging the structural features of quinone 4 (2-phenoxynaphthalene-1,4-dione) with those of phenolic constituents from cashew nut shell liquid (CNSL). CNSL is a waste product from cashew nut processing factories, with great potential as a source of drug precursors. The synthesized compounds were tested against Trypanosoma brucei brucei, including

  在为人类非洲锥虫病 (HAT) 寻找有效且可持续的药物的过程中，我们通过将醌 4（2-苯氧基萘-1,4-二酮）的结构特征与腰果壳油中的酚类成分的结构特征相结合，开发出了混合化合物（ CNSL)。CNSL是腰果加工厂的一种废品，作为药物前体的来源具有很大的潜力。合成的化合物针对布鲁氏锥虫进行了测试，包括三种多重耐药菌株、刚果锥虫和一种人类细胞系。发现最有效的活性是针对 T. b. 布鲁氏菌，HAT 的病原体。短链衍生物 20 (2-(3-(8-羟基辛基)苯氧基)-5-甲氧基萘-1,4-二酮)和 22 (5-羟基-2-(3-(8-羟基辛基)苯氧基)萘- 1,4-二酮）比 4 更活跃，显示出快速的微摩尔级锥虫杀灭活性，并且没有人类细胞毒性。探索它们对锥虫的作用方式的初步研究表明，ATP 耗竭，随后是线粒体膜去极化和线粒体超微结构损伤。这伴随着活性氧的产生。我们设想，从可再生且廉价的材料中获得的此
• Sustainable Drug Discovery of Multi-Target-Directed Ligands for Alzheimer’s Disease
  作者：Michele Rossi、Michela Freschi、Luciana de Camargo Nascente、Alessandra Salerno、Sarah de Melo Viana Teixeira、Florian Nachon、Fabien Chantegreil、Ondrej Soukup、Lukáš Prchal、Marco Malaguti、Christian Bergamini、Manuela Bartolini、Cristina Angeloni、Silvana Hrelia、Luiz Antonio Soares Romeiro、Maria Laura Bolognesi

  DOI：10.1021/acs.jmedchem.1c00048

  日期：2021.4.22

  The multifactorial nature of Alzheimer’s disease (AD) is a reason for the lack of effective drugs as well as a basis for the development of “multi-target-directed ligands” (MTDLs). As cases increase in developing countries, there is a need of new drugs that are not only effective but also accessible. With this motivation, we report the first sustainable MTDLs, derived from cashew nutshell liquid (CNSL)

  阿尔茨海默病（AD）的多因素性质是缺乏有效药物的原因，也是开发“多靶点定向配体”（MTDL）的基础。随着发展中国家病例的增加，需要不仅有效而且易于获得的新药。出于这个动机，我们报告了第一个可持续的 MTDL，它源自腰果壳液 (CNSL)，这是一种具有抗炎特性的廉价食物垃圾。我们应用了功能化 CNSL 组件和成熟的乙酰胆碱酯酶 (AChE)/丁酰胆碱酯酶 (BChE) 他克林模板的框架组合。 MTDL 是根据肝、神经元和小胶质细胞毒性来选择的。酶学研究揭示了有效且选择性的AChE /BChE 抑制剂（ 5、6和12 ），具有亚纳摩尔级活性。与 BChE 复合的5的 X 射线晶体结构使观察到的活性合理化 (0.0352 nM)。对 BV-2 小胶质细胞的研究揭示了5和6 （已经在 0.01 μM）的抗神经炎症和神经保护活性，证实了设计原理。
• MULTIFUNCTIONAL ALCOHOLS OBTAINED FROM CARDANOL, MULTIFUNCTIONAL ACRYLIC CROSSLINKER AND PENDANT PHOSPHOROUS FLAME RETARDANT DERIVATIVES THEREOF
  申请人：Prasad Vadakkethonippurathu Sivankutty Nair

  公开号：US20090240078A1

  公开（公告）日：2009-09-24

  Multifunctional alcohols, polyols derived from cardanol containing at least 3 hydroxyl groups are disclosed. Such alcohols allow for synthesis of multifunctional crosslinkers such as acrylates, epoxies, and vinyl ethers and flame retardants such as >phosphates. The multifunctional alcohols or polyols can be used in polyurethanes and polycarbonates. The multifunctional crosslinkers can be used in optical coating and waveguide compositions to increase curing speed and crosslink density. The multifunctional phosphates can be used in flame resistant plastics as the highly pendant phosphorus containing phosphate non-halogen flame retardant additives.

  本文介绍了从腰果酚衍生的多元醇聚醇，其中至少含有3个羟基。这种醇可用于合成多功能交联剂，如丙烯酸酯、环氧树脂和乙烯醚，以及阻燃剂，如磷酸盐。多功能醇或聚醇可用于聚氨酯和聚碳酸酯中。多功能交联剂可用于光学涂层和波导组合物中，以增加固化速度和交联密度。多功能磷酸盐可用于阻燃塑料中，作为高度悬挂的磷含量磷酸盐非卤素阻燃添加剂。
• Discovery of sustainable drugs for Alzheimer's disease: cardanol-derived cholinesterase inhibitors with antioxidant and anti-amyloid properties
  作者：Giselle de Andrade Ramos、Andressa Souza de Oliveira、Manuela Bartolini、Marina Naldi、Irene Liparulo、Christian Bergamini、Elisa Uliassi、Ling Wu、Paul E. Fraser、Monica Abreu、Alessandra Sofia Kiametis、Ricardo Gargano、Edilberto Rocha Silveira、Guilherme D. Brand、Lukas Prchal、Ondřej Soukup、Jan Korábečný、Maria Laura Bolognesi、Luiz Antonio Soares Romeiro

  DOI：10.1039/d1md00046b

  日期：——

  As part of our efforts to develop sustainable drugs for Alzheimer's disease (AD), we have been focusing on the inexpensive and largely available cashew nut shell liquid (CNSL) as a starting material for the identification of new acetylcholinesterase (AChE) inhibitors. Herein, we decided to investigate whether cardanol, a phenolic CNSL component, could serve as a scaffold for improved compounds with

  作为开发治疗阿尔茨海默病 (AD) 的可持续药物的一部分，我们一直专注于廉价且大量可用的腰果壳液 (CNSL)，作为鉴定新型乙酰胆碱酯酶 (AChE) 抑制剂的起始材料。在此，我们决定研究腰果酚（一种酚类 CNSL 成分）是否可以作为具有抗淀粉样蛋白和抗氧化活性的改良化合物的支架。合成了十种带有完整酚官能团和氨甲基官能团的新衍生物，并首先测试了它们对乙酰胆碱酯酶和丁酰胆碱酯酶 (BChE) 的抑制效力。5和11被发现可以在个位数微摩尔浓度下抑制人类 BChE。透射电子显微镜揭示了五种衍生物调节 Aβ 聚集的潜力，包括5和11。在 HORAC 测定中，5和11作为羟基清除剂的表现与标准抗氧化剂阿魏酸类似。此外，在神经元细胞培养物的体外研究中，发现5和11在 10 μM 浓度下可有效抑制活性氧的产生。他们还表现出了良好的初始 ADME/Tox 特征。总体而言，这些结果表明 CNSL 是开发潜在的
• PPAR MODULATORS
  申请人：ROMEIRO Luiz Antonio Soares

  公开号：US20170121268A1

  公开（公告）日：2017-05-04

  The present application relates to amorfrutin analogs and uses as PPAR modulators for the treatment of metabolic syndrome, obesity, hyperlipidemia, elevated fasting blood glucose, elevated blood pressure, low HDL cholesterol, type 2 diabetes, cardiovascular disease, a neurodegenerative disease, malaria or irritable bowel syndrome.