4-[3-(Hydroxymethyl)-5-(3-hydroxyprop-1-enyl)-7-methoxy-2,3-dihydro-1-benzofuran-2-yl]-2,6-dimethoxyphenol | 172702-55-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 2-芳基苯并呋喃类黄酮
• 英文名称: 4-[3-(Hydroxymethyl)-5-(3-hydroxyprop-1-enyl)-7-methoxy-2,3-dihydro-1-benzofuran-2-yl]-2,6-dimethoxyphenol
• 英文别名: 4-[3-(hydroxymethyl)-5-(3-hydroxyprop-1-enyl)-7-methoxy-2,3-dihydro-1-benzofuran-2-yl]-2,6-dimethoxyphenol
• CAS: 172702-55-5
• 化学式: C₂₁H₂₄O₇
• 分子量: 388.417
• InChiKey: SGRRPSBKBJVKJE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  97.6
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  松柏醇 、 芥子醇 在 PRX₃₄ Arabidopsis thaliana peroxidase 、 双氧水 作用下， 生成 4-[3-(Hydroxymethyl)-5-(3-hydroxyprop-1-enyl)-7-methoxy-2,3-dihydro-1-benzofuran-2-yl]-2,6-dimethoxyphenol 、 、 、 、 、 、 4,4'-[六氢呋喃并[3,4-c]呋喃-1,4-二基]双(2-甲氧基苯酚) 、 (+)-丁香树脂酚 、 (±)-dehydrodiconiferyl alcohol
  参考文献：
  名称：

  Arabidopsis peroxidase-catalyzed copolymerization of coniferyl and sinapyl alcohols: Kinetics of an endwise process

  摘要：

  In order to determine the mechanism of the earlier copolymerization steps of two main lignin precursors, sinapyl (S) alcohol and coniferyl (G) alcohol, microscale in vitro oxidations were carried out with a PRX34 Arabidopsis thaliana peroxidase in the presence of H2O2. This plant peroxidase was found to have an in vitro polymerization activity similar to the commonly used horseradish peroxidase. The selected polymerization conditions lead to a bulk polymerization mechanism when G alcohol was the only phenolic substrate available. In the same conditions, the presence of S alcohol at a 50/50 S/G molar ratio turned this bulk mechanism into an endwise one. A kinetics monitoring (size-exclusion chromatography and liquid chromatography-mass spectrometry) of the different species formed during the first 24 h oxidation of the S/G mixture allowed sequencing the bondings responsible for oligomerization. Whereas G homodimers and GS heterodimers exhibit low reactivity, the SS pinoresinol structure act as a nucleating site of the polymerization through an endwise process. This study is particularly relevant to understand the impact of S units on lignin structure in plants and to identify the key step at which this structure is programmed. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2010.06.011

文献信息

• Arabidopsis peroxidase-catalyzed copolymerization of coniferyl and sinapyl alcohols: Kinetics of an endwise process
  作者：Nathalie Demont-Caulet、Catherine Lapierre、Lise Jouanin、Stéphanie Baumberger、Valérie Méchin

  DOI：10.1016/j.phytochem.2010.06.011

  日期：2010.10

  In order to determine the mechanism of the earlier copolymerization steps of two main lignin precursors, sinapyl (S) alcohol and coniferyl (G) alcohol, microscale in vitro oxidations were carried out with a PRX34 Arabidopsis thaliana peroxidase in the presence of H2O2. This plant peroxidase was found to have an in vitro polymerization activity similar to the commonly used horseradish peroxidase. The selected polymerization conditions lead to a bulk polymerization mechanism when G alcohol was the only phenolic substrate available. In the same conditions, the presence of S alcohol at a 50/50 S/G molar ratio turned this bulk mechanism into an endwise one. A kinetics monitoring (size-exclusion chromatography and liquid chromatography-mass spectrometry) of the different species formed during the first 24 h oxidation of the S/G mixture allowed sequencing the bondings responsible for oligomerization. Whereas G homodimers and GS heterodimers exhibit low reactivity, the SS pinoresinol structure act as a nucleating site of the polymerization through an endwise process. This study is particularly relevant to understand the impact of S units on lignin structure in plants and to identify the key step at which this structure is programmed. (C) 2010 Elsevier Ltd. All rights reserved.