1-(4-羟基-3-甲氧基苯基)丙烷-1,3-二醇 | 3063-86-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 中文名称: 1-(4-羟基-3-甲氧基苯基)丙烷-1,3-二醇
• 英文名称: 1-Guajacyl-propandiol-(1,3)
• 英文别名: 1-(4-Hydroxy-3-methoxyphenyl)propane-1,3-diol
• CAS: 3063-86-3
• 化学式: C₁₀H₁₄O₄
• 分子量: 198.219
• InChiKey: ZWZPBECHOLTFFT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  69.9
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(4-羟基-3-甲氧基苯基)丙烷-1,3-二醇 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 150.0 ℃ 、3.55 MPa 条件下， 反应 8.0h， 以74%的产率得到3-(4-羟基-3-甲氧基苯基)-1-丙醇
  参考文献：
  名称：

  Mechanistic investigation of the Zn/Pd/C catalyzed cleavage and hydrodeoxygenation of lignin

  摘要：

  当前生物精炼过程仅利用木质素的热值，而将木质素转化为高价值化学品是一个越来越受到关注的领域。

  DOI：

  10.1039/c5gc01325a
• 作为产物：
  描述：

  3-Acetoxy-1-(4-hydroxy-3-methoxy-phenyl)-propan-1-on 在 lithium aluminium tetrahydride 作用下， 生成 1-(4-羟基-3-甲氧基苯基)丙烷-1,3-二醇
  参考文献：
  名称：

  Freudenberg; Fuchs, Chemische Berichte, 1954, vol. 87, p. 1824,1828

  摘要：

  DOI：

文献信息

• Enzymatic cleavage of lignin β-O-4 aryl ether bonds via net internal hydrogen transfer
  作者：Jochen Reiter、Harald Strittmatter、Lars O. Wiemann、Doris Schieder、Volker Sieber

  DOI：10.1039/c3gc40295a

  日期：——

  The current greening of chemical production processes going along with a rising interest for the utilization of biogenic feedstocks recently revived the research to find new ways for the degradation of the complex lignin-backbone by means of biocatalysis and combined chemo-enzymatic catalysis. Lignin, which accumulates in 50 million t/a, is regarded as a potential substitute for phenolic and other aromatic, oil-based chemicals in the upcoming post oil age. The cleavage of the β-O-4-aryl ether linkage is the most favoured, since it accounts for approximately 50% of all ether linkages in lignin. This enzymatic cleavage was proposed to be a part of the lignin catabolism in the proteobacterium Sphingobium sp. SYK6. Three enzymes, LigD, a Cα-dehydrogenase, LigF, a β-etherase and LigG, a glutathione lyase, are supposed to be involved in lignin degradation. We cloned and recombinantly expressed these genes in E. coli and determined their pH and temperature optima on the lignin model substrate 1-(4-hydroxy-3-methoxyphenyl)-2-(2-methoxyphenoxy)-1,3-propanediol 1. Using an NAD+ dependent glutathione reductase from Allochromatium vinosum (AVR) we established an efficient way to regenerate the co-substrates NAD+ and glutathione allowing for a self-sufficient balanced enzymatic cascade with net internal hydrogen transfer (hydrogen borrowing). We showed the capability of this enzyme system to release lignin monomers from complex lignin structures coming from differently prepared real lignin substrates. This novel enzyme system could become a useful tool to release lignin monomers from complex lignin structures.

  随着化学生产过程的绿色化以及对生物源原料利用兴趣的上升，研究人员最近重新关注利用生物催化和联合化学-酶催化的新方法来降解复杂的木质素骨架。木质素的年累积量达到5000万吨，被视为即将到来的后石油时代中替代酚类及其他芳香油基化学品的潜在材料。木质素中的β-O-4-芳基醚键的断裂是最受欢迎的，因为它大约占木质素中所有醚键的50%。这种酶促断裂被认为是放线菌Sphingobium sp. SYK6中木质素分解代谢的一部分。三种酶，LigD（α-去氢酶）、LigF（β-醚化酶）和LigG（谷胱甘肽裂解酶），被认为参与木质素的降解。我们在大肠杆菌中克隆和重组表达了这些基因，并测定了它们在木质素模型底物1-(4-羟基-3-甲氧基苯基)-2-(2-甲氧基苯氧基)-1,3-丙二醇 1上的pH和温度最优值。通过使用来自Allochromatium vinosum（AVR）的NAD+依赖性谷胱甘肽还原酶，我们建立了一种有效的方式来再生辅助底物NAD+和谷胱甘肽，从而实现自给自足的平衡酶级联反应（氢借用）。我们展示了这一酶系统从不同准备的真实木质素底物中释放木质素单体的能力。这个新型酶系统可能成为从复杂木质素结构中释放木质素单体的有用工具。
• Enzymatic Specific Production and Chemical Functionalization of Phenylpropanone Platform Monomers from Lignin
  作者：Yukari Ohta、Ryoichi Hasegawa、Kanako Kurosawa、Allyn H. Maeda、Toshio Koizumi、Hiroshi Nishimura、Hitomi Okada、Chen Qu、Kaori Saito、Takashi Watanabe、Yuji Hatada

  DOI：10.1002/cssc.201601235

  日期：2017.1.20

  Although well-definable aromatic monomers have been obtained from synthetic lignin-model dimers, enzymatic-selective synthesis of platform monomers from natural lignin has not been accomplished. In this study, we successfully achieved highly specific synthesis of aromatic monomers with a phenylpropane structure directly from natural lignin using a cascade reaction of β-O-4-cleaving bacterial enzymes

  酶催化是一种从木质素生产高价值低分子量芳香族化合物的环保策略。尽管已经从合成木质素模型二聚体中获得了明确的芳香族单体，但从天然木质素中酶选择性合成平台单体尚未实现。在这项研究中，我们利用一锅中β-O-4-裂解细菌酶的级联反应，成功地直接从天然木质素中高度特异性地合成了具有苯丙烷结构的芳香族单体。愈创木酰羟基丙酮 (GHP) 和 GHP/紫丁香基羟基丙酮 (SHP) 混合物是从软木（柳杉）和硬木（蓝桉）中分离出的木质素的独特单体。酶反应中的中间产物显示出在酶的底物结合位点容纳高度异源底物的能力。为了证明 GHP 作为生物基工业平台化学品的适用性，我们通过化学方法生成生物基聚合物的增值 GHP 衍生物。与这些用于木质素衍生的苯丙酮单体增值的化学转化一起，直接从天然木质素中特异性酶促生产单体预计将为可持续生物精炼厂的“白色生物技术”提供新的途径。
• METHOD FOR PRODUCING PHENYL PROPANE-BASED COMPOUNDS USING ENZYMES
  申请人：Japan Agency for Marine-Earth Science and Technology

  公开号：EP3106522A1

  公开（公告）日：2016-12-21

  The object of the invention is to provide a method which, if compared with prior art, more specifically and efficiently produces a compound having a phenol propane structure from natural biomass containing lignins by causing enzymes to act on the biomass. The object is achieved by a method for producing a phenyl propane-based compound comprising a step of producing a phenyl propane-based compound by causing enzymes derived from microorganisms of the genus Novosphingobium to act on biomass containing lignins and/or lignin-related substances in the presence of NAD and reduction type glutathione.

  本发明的目的是提供一种方法，与现有技术相比，该方法通过使酶作用于生物质，从含有木质素的天然生物质中更具体、更有效地生产具有苯丙烷结构的化合物。 本发明的目的是通过一种生产苯基丙烷基化合物的方法来实现的，该方法包括以下步骤：在NAD和还原型谷胱甘肽存在的情况下，使来自新磷脂菌属微生物的酶作用于含有木质素和/或木质素相关物质的生物质，从而生产苯基丙烷基化合物。
• METHOD FOR PRODUCING PHENYL PROPANE-BASED COMPOUND USING MICRO-ORGANISMS
  申请人：Japan Agency for Marine-Earth Science and Technology

  公开号：EP3106523A1

  公开（公告）日：2016-12-21

  ABSTRACT The object of the invention is to provide a method which specifically and efficiently produces a compound having a phenol propane structure from natural biomass containing lignins by causing microorganisms to act on biomass. The object is achieved by a method for producing a phenyl propane-based compound comprising a step of producing a phenyl propane-based compound by causing microorganisms of the genus Novosphingobium to act on biomass containing lignins and/or lignin-related substances.

  摘要 本发明的目的是提供一种方法，通过使微生物作用于生物质，从含有木质素的天然生物质中特异而有效地生产具有苯丙烷结构的化合物。本发明的目的是通过一种生产苯基丙烷基化合物的方法来实现的，该方法包括一个步骤，即通过使新鞘氨醇属微生物作用于含有木质素和/或木质素相关物质的生物质来生产苯基丙烷基化合物。
• Resin for ink and ink
  申请人：HARIMA CHEMICALS, INCORPORATED

  公开号：US10781281B2

  公开（公告）日：2020-09-22

  A method for producing a resin for ink which includes reacting a lignin, a phenol, and an aldehyde so as to obtain a lignin-containing resol phenolic resin; and reacting the obtained lignin-containing resol phenolic resin with a rosin-based resin, and polyhydric alcohol.

  一种生产油墨用树脂的方法，包括使木质素、苯酚和醛发生反应，从而获得含木质素的分解酚醛树脂；以及使获得的含木质素的分解酚醛树脂与松香基树脂和多羟基乙醇发生反应。