4-hydroxyphenethyl 2-(4-hydroxyphenyl)acetate | 1162640-76-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 4-hydroxyphenethyl 2-(4-hydroxyphenyl)acetate
• 英文别名: 2-(4-hydroxyphenyl)ethyl 2-(4-hydroxyphenyl)acetate
• CAS: 1162640-76-7
• 化学式: C₁₆H₁₆O₄
• 分子量: 272.301
• InChiKey: NOVMMJPPPKMRRL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 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：

  4-苄氧基苯乙酸 在 4-二甲氨基吡啶 、 palladium on activated charcoal 、 四丁基氟化铵 、 氢气 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 生成 4-hydroxyphenethyl 2-(4-hydroxyphenyl)acetate
  参考文献：
  名称：

  Cytotoxic naphthoquinone and a new succinate ester from the soil fungus Fusarium solani PSU-RSPG227

  摘要：

  A new naphthoquinone, solaninaphthoquione (1), and a new succinate ester derivative, 4-(4-hydroxyphenethoxy)-4-oxobutanoic acid (2), were isolated from the soil fungus Fusarium solani PSU-RSPG227 together with five previously reported compounds; javanicin (3), monaspilosin (4), aspergillol B (5), tyrosol (6) and 4- hydroxyphenylacetic acid (7). Their structures were elucidated primarily by NMR spectroscopic data. Due to paucity of materials, compounds 2, 4 and 5 as well as analogues of 5 were prepared for biological activity evaluation. Compound 1 showed significant cytotoxic activity against breast cancer (MCF-7) cells and mild cytotoxic activity against oral human carcinoma (KB) cells (IC50 values of 21.3 and 22.6 mu M, respectively) compared to standard compounds. Compound 1 also displayed weak antimalarial activity (IC50 of 26.1 mu M). (C) 2014 Phytochemical Society of Europe. Published by Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.phytol.2014.11.018

文献信息

• POLYMERIC BIOMATERIALS DERIVED FROM PHENOLIC MONOMERS AND THEIR MEDICAL USES
  申请人：Rutgers, The State University of New Jersey

  公开号：US20130203713A1

  公开（公告）日：2013-08-08

  The present invention provides new classes of phenol compounds, including those derived from tyrosol and analogues, useful as monomers for preparation of biocompatible polymers, and biocompatible polymers prepared from these monomeric phenol compounds, including novel biodegradable and/or bioresorbable polymers. These biocompatible polymers or polymer compositions with enhanced bioresorbabilty and processibility are useful in a variety of medical applications, such as in medical devices and controlled-release therapeutic formulations. The invention also provides methods for preparing these monomeric phenol compounds and biocompatible polymers.

  本发明提供了新型酚类化合物，包括从酪醇和类似物中衍生的化合物，用作生物相容性聚合物的单体，以及从这些单体酚化合物制备的生物相容性聚合物，包括新型可降解和/或可吸收的聚合物。这些生物相容性聚合物或具有增强生物吸收性和加工性能的聚合物组合物在各种医疗应用中非常有用，例如在医疗器械和控释治疗配方中。该发明还提供了制备这些单体酚化合物和生物相容性聚合物的方法。
• [EN] DEGRADABLE PHASE CHANGING POLYMERS FOR DENTAL/MEDICAL APPLICATIONS<br/>[FR] POLYMÈRES À CHANGEMENT DE PHASE DÉGRADABLES POUR APPLICATIONS DENTAIRES/MÉDICALES
  申请人：UNIV RUTGERS

  公开号：WO2021055090A1

  公开（公告）日：2021-03-25

  A method of effectively and efficiently forming an implant. The method employs polymers having suitable mechanical properties and a desirable range of glass transition temperatures. The ability to easily adapt pre- shaped polymer implants based on clinical need and harden the reshaped polymer upon exposure to a liquid medium make it suitable for a variety of clinical applications.

  一种有效且高效地形成植入物的方法。该方法采用具有合适机械性能和理想玻璃转变温度范围的聚合物。基于临床需要，能够轻松调整预成型聚合物植入物并在暴露于液体介质后使其硬化，使其适用于各种临床应用。
• Polymeric biomaterials derived from phenolic monomers and their medical uses
  申请人：Rutgers, The State University of New Jersey

  公开号：US10774030B2

  公开（公告）日：2020-09-15

  Disclosed are new classes of diphenol compounds, derived from tyrosol or tyrosol analogues and hydroxybenzoic acid, which are useful as monomers for preparation of biocompatible polymers. Also disclosed are biocompatible polymers prepared from these monomeric diphenol compounds, including novel biodegradable and/or bioresorbable polymers of formula. These biocompatible polymers or polymer compositions with enhanced bioresorbability and processibility are useful in a variety of medical applications, such as in medical devices and controlled-release therapeutic compositions. The invention also provides methods for preparing these monomeric diphenol compounds and biocompatible polymers.

  本发明公开了由酪醇或酪醇类似物和羟基苯甲酸衍生的新型二苯酚化合物，它们可用作制备生物相容性聚合物的单体。此外，还公开了由这些单体二苯酚化合物制备的生物相容性聚合物，包括新型生物可降解和/或生物可吸收的式聚合物。这些生物相容性聚合物或聚合物组合物具有增强的生物可吸收性和可加工性，可用于各种医疗应用，如医疗器械和控释治疗组合物。本发明还提供了制备这些单体二酚化合物和生物相容性聚合物的方法。
• Synthesized tyrosyl hydroxyphenylacetate, a novel antioxidant, anti-stress and antibacterial compound
  作者：Imen Aissa、Mohamed Bouaziz、Fakher Frikha、Riadh Ben Mansour、Youssef Gargouri

  DOI：10.1016/j.procbio.2012.09.016

  日期：2012.12

  New tyrosyl ester derivative, a naturally occurring phenol with interesting biological properties, has been synthesized in good yield by a direct esterification of tyrosol (Ty) with p-hydroxyphenylacetic acid (p-HPA) using Candida antarctica lipase as a catalyst. The response surface methodology was used to modulate the effects of the enzyme amount (10-50 mg), the tert-butanol/hexane (v/v) ratio (0.16-0.84), the temperature (35-55 degrees C) and the reaction time (15-45 h) on the tyrosyl hydroxyphenylacetate (Ty-HPA) conversion yield. Under the optimal predicted conditions (enzyme amount: 10 mg, solvents volume ratio 0.16, reaction temperature; 45 degrees C and 34 h of incubation), a high conversion yield of 79.33 +/- 4% was reached. The obtained ester was purified and characterized by NMR, LC/MS and FT-IR methods. ABTS free radical quenching potency demonstrated that the esterified tyrosol (Ty-HPA) was more effective than the natural separated antioxidants: Ty and p-HPA. Furthermore, when used at a non-cytotoxic concentration (100 mu M), tyrosyl ester showed significant effectiveness in preventing iron-induced oxidative stress in blood cells compared to the two separated compounds. The antibacterial activity of Ty, p-HPA, mixed solution of Ty + p-HPA and Ty-HPA was performed by determining the minimum inhibitory concentration (MIC) and minimum bactericidal concentration (MBC) using a micro-well dilution method. Compared to the separated substrates, synthesized ester exhibits the most antibacterial effect mainly against Gram+ bacteria. (C) 2012 Elsevier Ltd. All rights reserved.
• US9416090B2
  申请人：——

  公开号：US9416090B2

  公开（公告）日：2016-08-16