sinapyl p-coumarate | 186023-58-5

• 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: sinapyl p-coumarate
• 英文别名: [(E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enyl] (E)-3-(4-hydroxyphenyl)prop-2-enoate
• CAS: 186023-58-5
• 化学式: C₂₀H₂₀O₆
• 分子量: 356.375
• InChiKey: OHILCANPGNXJLQ-YZQQHVNFSA-N

物化性质

• 沸点：
  574.2±50.0 °C(Predicted)
• 密度：
  1.269±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  85.2
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  sinapyl p-coumarate 在 palladium on activated charcoal 氢气 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 以60%的产率得到dihydrosinapyl 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：

  反式芥子醇 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 sinapyl 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：US20130219547A1

  公开（公告）日：2013-08-22

  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转移酶的核酸以及feruloyl-CoA:monolignol转移酶酶，该酶能够将单体木质素酰基转移，例如p-香豆酰基，coniferyl香豆酰基和sinapyl香豆酰基，将其纳入植物的木质素中。
• 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。
• 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。
• Feruloyl-CoA:monolignol transferases
  申请人：WISCONSIN ALUMNI RESEARCH FOUNDATION

  公开号：US10883089B2

  公开（公告）日：2021-01-05

  The invention relates to feruloyl-CoA:monolignol transferase enzymes and nucleic acids encoding the feruloyl-CoA:monolignol transferase enzymes. The enzymes and/or the nucleic acids enable incorporation of monolignol ferulates into the lignin of plants. The monolignol ferulates include, for example, p-coumaryl ferulate, coniferyl ferulate, and/or sinapyl ferulate.

  本发明涉及阿魏酰-CoA：单木质素转移酶和编码阿魏酰-CoA：单木质素转移酶的核酸。这些酶和/或核酸可以将单木酚阿魏酸酯掺入植物的木质素中。例如，单木质素阿魏酸酯包括对羟基阿魏酸酯、针叶基阿魏酸酯和/或山奈基阿魏酸酯。