dehydrodiconiferyl alcohol | 528814-97-3

• 物质功能分类: 有机原料 - 醇、酚、酚醇类化合物及衍生物
• 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: dehydrodiconiferyl alcohol
• 英文别名: 4-[3-(hydroxymethyl)-5-[(E)-3-hydroxyprop-1-en-1-yl]-7-methoxy-2,3-dihydro-1-benzofuran-2-yl]-2-methoxyphenol；4-[3-hydroxymethyl-5-(3-hydroxy-propenyl)-7-methoxy-2,3-dihydro-benzofuran-2-yl]-2-methoxy-phenol；Dehydro-dihydro-coniferyl-alkohol；Dehydro-diconiferyl-alkohol；Dehydro-diconiferylalkohol；Dehydrodiconiferyl-alkohol；4-[3-(hydroxymethyl)-5-[(E)-3-hydroxyprop-1-enyl]-7-methoxy-2,3-dihydro-1-benzofuran-2-yl]-2-methoxyphenol
• CAS: 528814-97-3
• 化学式: C₂₀H₂₂O₆
• 分子量: 358.391
• InChiKey: KUSXBOZNRPQEON-ONEGZZNKSA-N

物化性质

• 沸点：
  562.0±50.0 °C(Predicted)
• 密度：
  1.292±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  88.4
• 氢给体数：
  3
• 氢受体数：
  6

安全信息

• 储存条件：
  2-8℃

制备方法与用途

(E)-脱氢异烟肼醇表现出良好的对hCA IX和hCA XII的双重抑制作用[1]。此外，该化合物能够抑制愈合区结缔组织中NF-κB的核转位[2]。

反应信息

• 作为反应物：
  描述：

  dehydrodiconiferyl alcohol 生成 Balaphonin
  参考文献：
  名称：

  CEMEHOBA, E. I., SB. TR.,(1988) N7, S. 74-82

  摘要：

  DOI：
• 作为产物：
  描述：

  香草乙酮 在 carrageenan gel 、 双氧水 、 horseradish peroxidase 作用下， 以 phosphate buffer 、 丙酮 为溶剂， 反应 20.0h， 生成 dehydrodiconiferyl alcohol
  参考文献：
  名称：

  Regioselectivity in oxidative cross-coupling of phenols. Application to the synthesis of dimeric neolignans

  摘要：

  The problems of regioselectivity in oxidative coupling of phenols are outlined, and recent research on the application to the synthesis of lignans and neolignans is reviewed. Lignans and neolignans are dimers that are typically formed by oxidative coupling of propenyl phenols. The coupling of structurally different phenols (cross-coupling) is an extension of this synthesis. Recent results show that cross-coupling can be achieved if the phenols have compatible reactivities. The regioselectivity is often quite different in cross-coupling compared to dimerization. Coupling of phenols with widely different rates of oxidation is difficult but can be achieved if the concentration of the more reactive phenol can be kept low enough during the reaction, for instance by diffusion through a dialysis membrane. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00943-1

文献信息

• Phenolic compounds from roots of Urtica dioica
  作者：Rupert Kraus、Gerhard Spiteller

  DOI：10.1016/0031-9422(90)80140-c

  日期：1990.1

  Abstract Root extracts from Urtica dioica were separated into several classes of compounds by extraction with organic solvents at different pH values. The phenolic fraction was analysed by GC-MS after trimethylsilylation. This procedure allowed the identification of 18 phenolic compounds as well as the detection of eight lignans. The occurrence of some of these substances in this plant was previously

  摘要 通过用不同pH 值的有机溶剂提取，荨麻根提取物被分离成几类化合物。在三甲基甲硅烷基化后通过 GC-MS 分析酚级分。该程序允许识别 18 种酚类化合物以及检测 8 种木脂素。这些物质中的一些在这种植物中的存在以前是未知的。
• Synthesis and Characterization of New 5-Linked Pinoresinol Lignin Models
  作者：Fengxia Yue、Fachuang Lu、Runcang Sun、John Ralph

  DOI：10.1002/chem.201201506

  日期：2012.12.14

  alcohol producing pinoresinol‐containing trimers (and higher oligomers) in addition to other homo‐ and cross‐coupled products. Eight new lignin model compounds were obtained and characterized by NMR spectroscopy, and one tentatively identified cross‐coupled β‐O‐4′‐product was formed from a coniferyl alcohol 5‐O‐4′‐linked dimer. It was demonstrated that the 5‐5′‐ and 5‐O‐4′‐linked pinoresinol structures could

  松脂醇结构具有木质素单体单元之间的β-β'键，在软木木质素以及双子叶植物和单子叶植物中，特别是在丁香基特异性基因中被下调的那些中，都非常重要。虽然容易通过NMR光谱检测，松脂醇结构主要由β-醚裂解降解逃过检测分析推测由于联系的在5个位置的存在下，在5-5'-或5- ö -4'-结构。在这项研究中，旨在通过提供NMR表征所需的数据来帮助更好地理解5-连接的松脂醇结构，新的木质素模型化合物是通过仿生过氧化物酶介导的预制（游离酚）松柏树醇之间的氧化偶联反应合成的5‐5′‐或5‐ O‐4′-连接的二聚体和松柏醇单体。结果发现，除其他均相和交联产物外，此类含有游离酚类松柏醇部分的二聚体还可与产生松柏醇的三聚松脂（及高级低聚物）的松柏醇交叉偶联。获得和表征通过NMR谱八个新木质素模型化合物，和一种初步确定交叉耦合β -O- 4'-产物从一个松柏醇形成5- ö -4'-连接的二聚体。证明了5‐5′‐和5‐
• METHOD OF SELECTIVELY OXIDIZING LIGNIN
  申请人：Wisconsin Alumni Research Foundation

  公开号：US20190177259A1

  公开（公告）日：2019-06-13

  A method of selectively reacting lignin or a lignin-derived reactant to yield an aromatic product. The method includes the step of reacting lignin or a lignin-derived reactant with a molybdenum-containing catalyst, in a solvent, and optionally in the presence of an oxidant, for a time and a temperature wherein at least a portion of the lignin or lignin-derived reactant is selectively converted into an aromatic product, preferably coniferaldehyde and/or sinapaldehyde.

  一种选择性地将木质素或木质素衍生反应物反应以产生芳香产物的方法。该方法包括以下步骤：将木质素或木质素衍生反应物与含钼催化剂在溶剂中反应，可选地在氧化剂的存在下，在一定时间和温度下，使至少部分木质素或木质素衍生反应物选择性地转化为芳香产物，最好是对香豆醛和/或丁香豆醛。
• Regioselectivity in lignin biosynthesis. The influence of dimerization and cross-coupling
  作者：Kaisa Syrjänen、Gösta Brunow

  DOI：10.1039/a907919j

  日期：——

  We have studied the regioselectivity of oxidative phenol coupling in lignin formation using an oxidation system that distinguishes between dimerization reactions and cross-coupling reactions. We found that the regioselectivity of coupling was different in the two reactions. For instance, in coniferyl alcohol dimerization the formation of β–5 coupling product has a slight prevalence over the formation of β–O-4 product; in cross-coupling the β–O-4 mode is favoured in a ratio of ≈10∶1. This ratio is higher than that found in isolated softwood lignins. The degree of cross-coupling was influenced only to a small extent by changes in the rates of conventional addition of coniferyl alcohol (Zulauf versus Zutropf conditions). We found that diffusion through a dialysis membrane did effectively suppress the dimerization of coniferyl alcohol. Of the different oxidants investigated, manganese triacetate in acetic acid yielded the highest proportion of cross-coupling product.

  我们利用一种区分二聚反应和交叉偶联反应的氧化体系，研究了木质素形成过程中氧化酚偶联的区域选择性。我们发现，在这两种反应中，偶联的区域选择性是不同的。例如，在针叶醇二聚反应中，β-5 偶联产物的形成略优于 β-O-4 产物的形成；而在交叉偶联反应中，β-O-4 模式的比例为 ≈10∶1。这一比例高于在分离的软木木质素中发现的比例。交叉偶联的程度仅在很小程度上受到针叶醇常规添加速率变化（祖劳夫条件与祖特洛夫条件）的影响。我们发现，通过透析膜的扩散确实有效地抑制了松柏醇的二聚化。在所研究的不同氧化剂中，乙酸中的三乙酸锰产生的交叉偶联产物比例最高。
• Lignans from the Roots of<i>Urtica dioica</i>and their Metabolites Bind to Human Sex Hormone Binding Globulin (SHBG)
  作者：Matthias Schöttner、Dietmar Ganßer、Gerhard Spiteller

  DOI：10.1055/s-2006-957756

  日期：1997.12

  Polar extracts of the stinging nettle (Urtica dioica L.) roots contain the lignans (+)-neoolivil, (-)-secoisolariciresinol, dehydrodiconiferyl alcohol, isolariciresinol, pinoresinol, and 3,4-divanillyltetrahydrofuran. These compounds were either isolated from Urtica roots, or obtained semisynthetically. Their affinity to human sex hormone binding globulin (SHBG) was tested in an in vitro assay. In addition, the main intestinal transformation products of plant lignans in humans, enterodiol and entero-lactone, together with enterofuran were checked for their activity. All lignans except (-)-pinoresinol developed a binding affinity to SHBG in the in vitro assay. The affinity of (-)-3,4-divanillyltetrahydrofuran was outstandingly high. These findings are discussed with respect to potential beneficial effects of plant lignans on benign prostatic hyperplasia (BPH).

  刺荨麻（Urtica dioica L.）根的极性萃取物中含有木脂素（+）-neoolivil、（-）-secoisolariciresinol、dehydrodiconiferyl alcohol、isariciresinol、pinoresinol 和 3,4-divanillyltetrahydrofuran。这些化合物或从荨麻根中分离出来，或通过半合成方法获得。在体外试验中测试了它们与人类性激素结合球蛋白（SHBG）的亲和力。此外，还检测了植物木酚素在人体肠道中的主要转化产物肠二醇和肠内酯以及肠呋喃的活性。在体外试验中，除 (-)-pinoresinol 外，所有木酚素都与 SHBG 具有结合亲和力。(-)-3,4-divanillyltetrahydrofuran 的亲和力非常高。这些研究结果讨论了植物木酚素对良性前列腺增生症（BPH）的潜在有益作用。