2-丙烯酸,3-(4-羟基苯基)-,(2E)-3-(4-羟基苯基)-2-丙烯基酯,(2E)- | 122135-45-9

• 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
• 中文名称: 2-丙烯酸,3-(4-羟基苯基)-,(2E)-3-(4-羟基苯基)-2-丙烯基酯,(2E)-
• 英文名称: p-coumaryl coumarate
• 英文别名: 4-Coumaryl-4-coumarate；[(E)-3-(4-hydroxyphenyl)prop-2-enyl] (E)-3-(4-hydroxyphenyl)prop-2-enoate
• CAS: 122135-45-9
• 化学式: C₁₈H₁₆O₄
• 分子量: 296.323
• InChiKey: AMABNLPAOLRCOD-BRPQVOEQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  在 哌嗪 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以80%的产率得到2-丙烯酸,3-(4-羟基苯基)-,(2E)-3-(4-羟基苯基)-2-丙烯基酯,(2E)-
  参考文献：
  名称：

  Chavicol formation in sweet basil (Ocimum basilicum): cleavage of an esterified C9 hydroxyl group with NAD(P)H-dependent reduction

  摘要：

  丙烯基和烯丙基苯酚（如甲基茶维醇、对乙醇和丁香酚）作为调味剂和 9,9′-脱氧木酚素生物合成的假定前体（其中许多具有潜在的药用价值），其重要性日益凸显。然而，尽管经过了几十年的研究，丙烯基/烯丙基酚的完整生物合成途径仍未见报道。我们对一种积累了相对大量最简单挥发性烯丙基酚（甲基芹维醇）的泰国罗勒品种进行了体内放射性标记前体给药和体外蛋白质制备试验。通过这些实验，证明了俏皮醇的生物合成是通过苯丙醇途径转化为对迷迭香醇的。研究了导致后者脱氧的各种可能性，包括还原侧链双键形成对二氢香豆醇，然后脱水生成茶维醇，以及形成对甲氧基肉桂醇，进一步修饰侧链生成甲基茶维醇。研究的第三种可能性是通过酯化等方式活化对羟基肉桂醇的侧链醇，从而通过还原消除形成更容易离开的基团。研究表明，将对香豆素酯作为 NAD(P)H 依赖性还原酶的潜在底物，可以生成茶维醇，然后将茶维醇 O-甲基化，生成甲基茶维醇。

  DOI：

  10.1039/b605407b

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。
• 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。
• P-coumaroyl-CoA:monolignol transferases
  申请人：WISCONSIN ALUMNI RESEARCH FOUNDATION

  公开号：US10883090B2

  公开（公告）日：2021-01-05

  The invention is directed to p-coumaroyl-CoA:monolignol transferase enzymes, nucleic acids encoding p-coumaroyl-CoA:monolignol transferase enzymes, and inhibitory nucleic acids adapted to inhibit the expression and/or translation of p-coumaroyl-CoA:monolignol transferase RNA; expression cassettes, plant cells, and plants that have or encode such nucleic acids and enzymes; and methods of making and using such nucleic acids, enzymes, expression cassettes, cells, and plants.

  本发明涉及对香豆酰-CoA:单木质素转移酶、编码对香豆酰-CoA:单木质素转移酶的核酸、抑制对香豆酰-CoA:单木质素转移酶的表达和/或翻译的抑制性核酸；具有或编码这种核酸和酶的表达盒、植物细胞和植物；以及制造和使用这种核酸、酶、表达盒和植物的方法：单木质素转移酶 RNA；具有或编码这种核酸和酶的表达盒、植物细胞和植物；以及制造和使用这种核酸、酶、表达盒、细胞和植物的方法。
• GENES ENCODING CHAVICOL/EUGENOL SYNTHASE FROM THE CREOSOTE BUSH LARREA TRIDENTATA
  申请人：Lewis Norman G.

  公开号：US20100031398A1

  公开（公告）日：2010-02-04

  Particular aspects provide novel methods for redirecting carbon allocation in plants or cell culture from lignification to inherently more useful and tractable materials, and to facilitate the generation of, e.g., biofuels from the remaining plant roculture biomass. Particular aspects provided novel methods for converting monolignols into allyl/propenyl phenols, and for chavicol/eugenol formation or production. Additional aspects relate to the discovery of novel chavicol/eugenol synthases that convert p-coumaryl/coniferyl alcohol esters into chavicol/eugenol, and to novel compositions (e.g., novel proteins and nucleic acids encoding same), and novel methods using same for producing or forming chavicol/eugenol and other derivatives in cell culture and/or genetically modified plants, and for re-engineering the composition of plant biomass. Particular aspects provide novel methods for generation in culture or in planta of liquid/combustible allyl/propenyl phenols, and these phenolic products are utilized for (non-ethanol) biofuel/bioenergy purposes, while the remaining plant biomass facilitates the generation of other biofuels.
• P-COUMAROYL-COA:MONOLIGNOL TRANSFERASES
  申请人：WISCONSIN ALUMNI RESEARCH FOUNDATION

  公开号：US20210095263A1

  公开（公告）日：2021-04-01

  The invention is directed to p-coumaroyl-CoA:monolignol transferase enzymes, nucleic acids encoding p-coumaroyl-CoA:monolignol transferase enzymes, and inhibitory nucleic acids adapted to inhibit the expression and/or translation of p-coumaroyl-CoA:monolignol transferase RNA; expression cassettes, plant cells, and plants that have or encode such nucleic acids and enzymes; and methods of making and using such nucleic acids, enzymes, expression cassettes, cells, and plants.