Coniferyl p-coumarate | 67638-41-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: Coniferyl p-coumarate
• 英文别名: [(E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enyl] (E)-3-(4-hydroxyphenyl)prop-2-enoate
• CAS: 67638-41-9
• 化学式: C₁₉H₁₈O₅
• 分子量: 326.349
• InChiKey: UPNLRNQUIJXYPN-LFWRRJNUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  76
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Coniferyl p-coumarate 在 palladium on activated charcoal 氢气 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 生成 dihydroconiferyl dihydro-p-coumarate
  参考文献：
  名称：

  p-coumaroylated syringyl units in maize lignin: Implications for β-ether cleavage by thioacidolysis

  摘要：

  Recent NMR studies of lignin isolated from maize demonstrated that p-coumarate esters are attached exclusively to the gamma-position of phenylpropane side chains. Thioacidolysis/desulphuration experiments have revealed that p-coumarate units are attached primarily (ca 90%) to syringyl moieties in maize lignin. In model studies with guaiacylglycerol and syringylglycerol-beta-guaiacyl ethers, cleavage of beta-ether linkages by thioacidolysis was reduced 40% by gamma-acylation of phenylpropane side chains with p-coumarate. Our results indicate that gamma-p-coumarate esters significantly reduce the yields of syringyl products recovered after thioacidolysis of grass lignins.

  DOI：

  10.1016/s0031-9422(96)00431-1
• 作为产物：
  描述：

  反式-3-(4-羟基-3-甲氧基苯基)-2-丙烯-1-醇 在 哌嗪 、 4-二甲氨基吡啶 、 碳酸氢钠 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 27.0h， 生成 Coniferyl p-coumarate
  参考文献：
  名称：

  p-coumaroylated syringyl units in maize lignin: Implications for β-ether cleavage by thioacidolysis

  摘要：

  Recent NMR studies of lignin isolated from maize demonstrated that p-coumarate esters are attached exclusively to the gamma-position of phenylpropane side chains. Thioacidolysis/desulphuration experiments have revealed that p-coumarate units are attached primarily (ca 90%) to syringyl moieties in maize lignin. In model studies with guaiacylglycerol and syringylglycerol-beta-guaiacyl ethers, cleavage of beta-ether linkages by thioacidolysis was reduced 40% by gamma-acylation of phenylpropane side chains with p-coumarate. Our results indicate that gamma-p-coumarate esters significantly reduce the yields of syringyl products recovered after thioacidolysis of grass lignins.

  DOI：

  10.1016/s0031-9422(96)00431-1

文献信息

• p-Coumaroyl-CoA:Monolignol Transferase
  申请人：Sedbrook John

  公开号：US20160046955A1

  公开（公告）日：2016-02-18

  The invention relates to nucleic acids encoding a p-coumaroyl-CoA:monolignol transferase and to inhibitory nucleic acids adapted to inhibit the expression and/or translation of a p-coumaroyl-CoA:monolignol transferase RNA. Inhibition of p-coumaroyl-CoA:monolignol transferase in plants improves the incorporation of monolignol ferulates into the lignin of plants, giving rise to plant biomass that is more easily processed into useful products such as paper and biofuels.

  该发明涉及编码p-香豆酰辅酶A：单木质素转移酶的核酸，以及适用于抑制p-香豆酰辅酶A：单木质素转移酶RNA表达和/或翻译的抑制性核酸。在植物中抑制p-香豆酰辅酶A：单木质素转移酶可改善单木质素酰基的纤维素中的结合，使得植物生物质更容易加工成纸张和生物燃料等有用产品。
• FERULOYL-CoA:MONOLIGNOL TRANSFERASE
  申请人：Wilkerson Curtis

  公开号：US20130203973A1

  公开（公告）日：2013-08-08

  The invention relates to nucleic acids encoding a feruloyl-CoA:monolignol transferase and the feruloyl-CoA:monolignol transferase enzyme that enables incorporation of monolignol ferulates, for example, including p-coumaryl ferulate, coniferyl ferulate, and sinapyl ferulate, into the lignin of plants.

  该发明涉及编码feruloyl-CoA: monolignol转移酶的核酸和feruloyl-CoA: monolignol转移酶酶，该酶使得单木素ferulates（例如p-香豆素ferulate、coniferyl ferulate和sinapyl ferulate）能够被结合到植物的木质素中。
• FERULOYL-CoA:MONOLIGNOL-TRANSFERASE
  申请人：Board of Trustees of Michigan State University

  公开号：EP3138919A1

  公开（公告）日：2017-03-08

  The invention relates to nucleic acids encoding a feruloyl-CoA:monolignol transferase and the feruloyl-CoA:monolignol transferase enzyme that enables incorporation of monolignol ferulates, for example, including p-coumaryl ferulate, coniferyl ferulate, and sinapyl ferulate, into the lignin of plants.

  本发明涉及编码阿魏酰-CoA:单木质素转移酶的核酸和阿魏酰-CoA:单木质素转移酶，该酶可将单木质素阿魏酸酯（例如包括对羟基阿魏酸酯、针叶阿魏酸酯和山奈阿魏酸酯）掺入植物的木质素中。
• Hibiscus cannabinus feruloyl-CoA:monolignol transferase
  申请人：Wisconsin Alumni Research Foundation (WARF)

  公开号：US10059955B2

  公开（公告）日：2018-08-28

  The invention relates to isolated nucleic acids encoding a feruloyl-CoA:monolignol transferase and feruloyl-CoA:monolignol transferase enzymes. The isolated nucleic acids and/or the enzymes enable incorporation of monolignol ferulates into the lignin of plants, where such monolignol ferulates include, for example, p-coumaryl ferulate, coniferyl ferulate, and/or sinapyl ferulate. The invention also includes methods and plants that include nucleic acids encoding a feruloyl-CoA:monolignol transferase enzyme and/or feruloyl-CoA:monolignol transferase enzymes.

  本发明涉及编码阿魏酰-CoA:单木质素转移酶和阿魏酰-CoA:单木质素转移酶的分离核酸。分离的核酸和/或酶可将单木质素阿魏酸酯掺入植物的木质素中，这些单木质素阿魏酸酯包括对羟基阿魏酸酯、针叶阿魏酸酯和/或山奈阿魏酸酯。本发明还包括包括编码阿魏酰-CoA:单木质素转移酶和/或阿魏酰-CoA:单木质素转移酶的核酸的方法和植物。
• P-coumaroyl-CoA:monolignol transferase
  申请人：Wisconsin Alumni Research Foundation

  公开号：US10428342B2

  公开（公告）日：2019-10-01

  The invention relates to nucleic acids encoding a p-coumaroyl-CoA:monolignol transferase and to inhibitory nucleic acids adapted to inhibit the expression and/or translation of a p-coumaroyl-CoA:monolignol transferase RNA. Inhibition of p-coumaroyl-CoA:monolignol transferase in plants improves the incorporation of monolignol ferulates into the lignin of plants, giving rise to plant biomass that is more easily processed into useful products such as paper and biofuels.

  本发明涉及编码对香豆酰-CoA:单木质素转移酶的核酸，以及适于抑制对香豆酰-CoA:单木质素转移酶 RNA 表达和/或翻译的抑制性核酸。抑制植物中的对香豆酰-CoA:单木质素转移酶可改善单木质素铁与植物木质素的结合，从而产生更容易加工成有用产品（如纸张和生物燃料）的植物生物质。