(Z)-3-(4-Hydroxy-3-methoxy-phenyl)-2-(2-methoxy-phenoxy)-propenal

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: (Z)-3-(4-Hydroxy-3-methoxy-phenyl)-2-(2-methoxy-phenoxy)-propenal
• 英文别名: (Z)-3-(4-hydroxy-3-methoxyphenyl)-2-(2-methoxyphenoxy)prop-2-enal
• 化学式: C₁₇H₁₆O₅
• 分子量: 300.311
• InChiKey: BFNVOQPVGCQUBU-LCYFTJDESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3-(4-hydroxy-3-methoxyphenyl)-2-(2-methoxyphenoxy)-2-propenol 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 为溶剂， 生成 (Z)-3-(4-Hydroxy-3-methoxy-phenyl)-2-(2-methoxy-phenoxy)-propenal
  参考文献：
  名称：

  Cross-Coupling of Hydroxycinnamyl Aldehydes into Lignins

  摘要：

  [GRAPHICS]Pathways for hydroxycinnamyl aldehyde incorporation into lignins are revealed by examining transgenic plants deficient in cinnamyl alcohol dehydrogenase, the enzyme that converts hydroxycinnamyl aldehydes to the hydroxycinnamyl alcohol lignin monomers. In such plants the aldehydes incorporate into lignins via radical coupling reactions. As diagnostically revealed by long-range C-13-H-1 correlative NMR, sinapyl aldehyde (3,5-dimethoxy 4-hydroxy-cinnamaldehyde) 8-O-4-cross-couples with both gualacyl (3-methoxy-4-hydroxyphenyl-propanoid) and syringyl (3,5-dimethoxy-4-hydroxyphenyl-propanoid) units, whereas coniferyl aldehyde cross-couples only with syringyl units.

  DOI：

  10.1021/ol005906o

文献信息

• 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.
• US9131648B2
  申请人：——

  公开号：US9131648B2

  公开（公告）日：2015-09-15
• Cross-Coupling of Hydroxycinnamyl Aldehydes into Lignins
  作者：Hoon Kim、John Ralph、Nabila Yahiaoui、Michel Pean、Alain-M. Boudet

  DOI：10.1021/ol005906o

  日期：2000.7.1

  [GRAPHICS]Pathways for hydroxycinnamyl aldehyde incorporation into lignins are revealed by examining transgenic plants deficient in cinnamyl alcohol dehydrogenase, the enzyme that converts hydroxycinnamyl aldehydes to the hydroxycinnamyl alcohol lignin monomers. In such plants the aldehydes incorporate into lignins via radical coupling reactions. As diagnostically revealed by long-range C-13-H-1 correlative NMR, sinapyl aldehyde (3,5-dimethoxy 4-hydroxy-cinnamaldehyde) 8-O-4-cross-couples with both gualacyl (3-methoxy-4-hydroxyphenyl-propanoid) and syringyl (3,5-dimethoxy-4-hydroxyphenyl-propanoid) units, whereas coniferyl aldehyde cross-couples only with syringyl units.