4-(1-hydroxyprop-2-enyl)guaiacol

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 4-(1-hydroxyprop-2-enyl)guaiacol
• 英文别名: 4-(1-hydroxyallyl)-2-methoxyphenol；1'-Hydroxyeugenol；4-(1-hydroxyprop-2-enyl)-2-methoxyphenol
• 化学式: C₁₀H₁₂O₃
• 分子量: 180.203
• InChiKey: CAQJZUXHKMYJEF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.62
• 重原子数：
  13.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  49.69
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  4-(1-hydroxyprop-2-enyl)guaiacol 在 S-α,α-双(3,5-二三氟甲基苯基)脯氨醇三甲基硅醚 、 sodium tetrahydroborate 、 bis(1,5-cyclooctadiene)diiridium(I) dichloride 、 5-((11bS)-dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin-4-yl)-5H-dibenzo[b,f]azepine 作用下， 以 甲醇 、 1,2-二氯乙烷 为溶剂， 反应 14.25h， 生成
  参考文献：
  名称：

  金属/手性胺共催化 α-烯丙基化和 [4+2] 环加成中的糖辅助动力学拆分：糖和色烷衍生物的高度对映选择性合成

  摘要：

  通过标题反应合成了功能化的丙糖、呋喃糖和苯并二氢吡喃衍生物。通过使用金属和手性胺助催化剂的简单组合，CC 键形成级联过程以高度对映选择性方式（高达 >99% ee）生成具有季立构中心的功能化糖衍生物。值得注意的是，当使用外消旋胺催化剂（0％ee）和金属催化剂的组合时，手性糖底物和手性氨基酸衍生物之间的相互作用允许构建具有高对映选择性（高达99％）的功能化糖产品。

  DOI：

  10.1002/chem.202301725
• 作为产物：
  描述：

  溴乙烯 、 香草醛 在 碘 、 magnesium 作用下， 以 乙醚 为溶剂， 反应 2.0h， 生成 4-(1-hydroxyprop-2-enyl)guaiacol
  参考文献：
  名称：

  Anti-proliferative, apoptotic induction, and anti-migration effects of hemi-synthetic 1&prime;<em>S</em>-1&prime;-acetoxychavicol acetate analogs on MDA-MB-231 breast cancer cells

  摘要：

  Nine analogs of 1' S-1'-acetoxychavicol acetate (ACA) were hemi-synthesized and evaluated for their anticancer activities against seven human cancer cell lines. The aim of this study was to investigate the anti-proliferative, apoptotic, and anti-migration effects of these compounds and to explore the plausible underlying mechanisms of action. We found that ACA and all nine analogs were non toxic to human mammary epithelial cells (HMECs) used as normal control cells, and only ACA, 1'-acetoxyeugenol acetate (AEA), and 1'-acetoxy-3,5-dimethoxychavicol acetate (AMCA) inhibited the growth of MDA-MB-231 breast cancer cells with a half-maximal inhibitory concentration (IC50) value of <30.0 mu M based on 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay results, and were selected for further investigation. DNA fragmentation assays showed that these three compounds markedly induced apoptosis of MDA-MB-231 cells. Western blot analysis revealed increased expression levels of cleaved PARP, p53, and Bax, while decreased expression levels of Bcl-2 and Bcl-xL were seen after treatment, indicating that apoptosis was induced via the mitochondrial pathway. Moreover, ACA, AEA, and AMCA effectively inhibited the migration of MDA-MB-231 cells. They also downregulated the expression levels of pFAK/FAK and pAkt/Akt via the integrin beta 1-mediated signaling pathway. Collectively, ACA and its hemi-synthetic analogs, AEA and AMCA are seen as potential anticancer agents following their abilities to suppress growth, induce apoptosis, and inhibit migration of breast cancer cells.

  DOI：

  10.2147/dddt.s130349

文献信息

• Non-plasmonic Ni nanoparticles catalyzed visible light selective hydrogenolysis of aryl ethers in lignin under mild conditions
  作者：Peifeng Li、Yixuan Ouyang、Gang Xiao、Yilin Zhao、Sarina Sarina、Jan Baeyens、Haijia Su、Huai-Yong Zhu

  DOI：10.1039/d1gc01953h

  日期：——

  solar-to-chemical conversion. We report a novel photocatalysis process for the selective hydrogenolysis of aryl ethers in lignin on a heterogeneous catalyst of non-precious Ni nanoparticles supported on ZrO2. Three aryl ether bonds in lignin were successfully cleaved under mild conditions with excellent conversion and good to excellent selectivity under visible light irradiation. We also used solar irradiation to

  广泛用于热催化的多功能 VIII 族金属的光驱动催化在太阳能到化学转化方面具有巨大潜力。我们报告了一种新的光催化工艺，用于在 ZrO 2上负载的非贵镍纳米颗粒的多相催化剂上选择性氢解木质素中的芳基醚. 木质素中的三个芳基醚键在温和条件下成功裂解，在可见光照射下具有优异的转化率和良好的选择性。我们还使用太阳辐射来证明总能耗显着降低。光照射激发了 Ni 纳米颗粒中的带间跃迁，由此产生的高能电子增强了芳醚的还原裂解活性。其应用潜力通过脱碱性木质素的解聚得到9.84wt%的总单体产率来说明，其中香草醛、愈创木酚和夹竹桃素作为三种主要产物。
• Flavorant compositions
  申请人：Givaudan Roure (International) SA

  公开号：US06476252B1

  公开（公告）日：2002-11-05

  The invention is related to a flavorant composition containing 1′-acetoxychavicol acetate and 1′-acetoxyeugenol acetate derivatives thereof as well as a flavorant acceptable carrier. The flavorant composition may be used for flavoring foods, beverages or healthcare products with warm/hot, spicy and pungent sensations related to Galangal.

  这项发明涉及一种含有1'-乙酰氧基巴豆酚醋酸酯和1'-乙酰氧基丁香酚醋酸酯衍生物的风味剂组合物，以及可接受的风味剂载体。该风味剂组合物可用于赋予食品、饮料或保健产品温暖/辣味和刺激感，与高良姜相关。
• Pungent flavor components
  申请人：Givaudan SA

  公开号：EP0933030B1

  公开（公告）日：2006-07-26
• HIGH PURITY LIGNIN, LIGNIN COMPOSITIONS, AND HIGHER STRUCTURED LIGNIN
  申请人：Renmatix Inc.

  公开号：EP2970595B1

  公开（公告）日：2018-07-11
• STAGED BIOMASS PYROLYSIS PROCESS AND APPARATUS
  申请人：Hornung Andreas

  公开号：US20110278149A1

  公开（公告）日：2011-11-17

  A biomass pyrolysis process in which biomass feedstock particles (having a d5o mean particle size of at least 1 mm) are thermally treated substantially in the absence of oxygen to pyrolyse the biomass feedstock particles. The thermal treatment of the biomass feedstock particles includes a heat treatment drying step at a temperature in the range 100° C. to 250° C. Then, at a pre-pyrolysis heating location in a heat treatment system, the biomass feedstock particles are heated to a temperature in the range 280° C. to 350° C., held within the same temperature range for a time of at least 5 seconds and then moved from the pre-pyrolysis heating location to a pyrolysis heating location by a conveyor system for heating to a temperature above 350° C. for pyrolysis.