methyl (E)-sinapate | 42041-51-0

• 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: methyl (E)-sinapate
• 英文别名: methyl sinapate；(E)-methyl 3-(4-hydroxy-3,5-dimethoxyphenyl)acrylate；methyl (E)-3-(4-hydroxy-3,5-dimethoxyphenyl)acrylate；sinapic acid methyl ester；(E)-sinapic acid methyl ester；methyl (E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoate
• CAS: 42041-51-0
• 化学式: C₁₂H₁₄O₅
• 分子量: 238.24
• InChiKey: JHLPYWLKSLVYOI-SNAWJCMRSA-N

物化性质

• 保留指数：
  2092.1

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl (E)-sinapate 在 sodium hydroxide 、 三氯化铁 作用下， 以 甲醇 为溶剂， 反应 64.0h， 生成 trans-7-hydroxy-1-(4-hydroxy-3,5-dimethoxyphenyl)-6,8-dimethoxy-1,2-dihydronaphthalene-2,3-dicarboxylic acid
  参考文献：
  名称：

  Sinapate Dehydrodimers and Sinapate−Ferulate Heterodimers in Cereal Dietary Fiber

  摘要：

  Two 8-8-coupled sinapic acid dehydrodimers and at least three sinapate-ferulate heterodimers have been identified as saponification products from different insoluble and soluble cereal grain dietary fibers. The two 8-8-disinapates were authenticated by comparison of their GC retention times and mass spectra with authentic dehydrodimers synthesized from methyl or ethyl sinapate using two different single-electron metal oxidant systems. The highest amounts (481 mug/g) were found in wild rice insoluble dietary fiber. Model reactions showed that it is unlikely that the dehydrodisinapates detected are artifacts formed from free sinapic acid during the saponification procedure. The dehydrodisinapates presumably derive from radical coupling of sinapate-polymer esters in the cell wall; the radical coupling origin is further confirmed by finding 8-8 and 8-5 (and possibly 8-O-4) sinapate-ferulate cross-products. Sinapates therefore appear to have an analogous role to ferulates in cross-linking polysaccharides in cereal grains and presumably grass cell walls in general.

  DOI：

  10.1021/jf020910v
• 作为产物：
  描述：

  3,5-二甲氧基-4-羟基肉桂酸 在 硫酸 作用下， 以 甲醇 为溶剂， 反应 5.0h， 生成 methyl (E)-sinapate
  参考文献：
  名称：

  O-甲基化对邻二取代苯酚碳13核磁共振信号的影响及其在结构测定中的应用。

  摘要：

  研究了 O-甲基化对正交二取代苯酚的碳-13 核磁共振化学位移的影响。在具有非共轭正交二取代基（1-10）的苯酚中，O-甲基化导致正交碳（C-2 和 -6）平均下移 5.2 ppm，对位碳（C-4）平均下移 4.6 ppm。这些移动值与在正一取代和正二取代苯酚中观察到的移动值明显不同。这种规律性对于解释某些具有正二取代酚基的天然产物的光谱以及确定甲氧基在此类化合物中的位置非常有用。从硅曲霉（Aspergillus silvaticus）中分离出了两种新的邻苯二甲酸酯，即硅烷醇（15）和 O-甲基硅烷醇（16）以及尼杜醇（17）。在确定这些化合物结构的过程中，成功地将正一取代酚和正二取代酚的 O-甲基化效应应用于这些邻苯二甲酸酯。硅烷醇和 O-甲基硅烷醇的结构分别被确定为 6-羟基-4-甲氧基-5-甲基邻苯二甲酸酯和 4，6-二甲氧基-5-甲基邻苯二甲酸酯。

  DOI：

  10.1248/cpb.32.2622

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 Antileukemic Activities of Piperlongumine and HDAC Inhibitor Hybrids against Acute Myeloid Leukemia Cells
  作者：Yi Liao、Xiaojia Niu、Bailing Chen、Holly Edwards、Liping Xu、Chengzhi Xie、Hai Lin、Lisa Polin、Jeffrey W. Taub、Yubin Ge、Zhihui Qin

  DOI：10.1021/acs.jmedchem.6b00772

  日期：2016.9.8

  Synergistic-to-additive antileukemic interactions of piperlongumine (PL) and HDAC inhibitor (HDACi) SAHA (Vorinostat) provide a compelling rationale to construct PL-HDACi hybrids, such as 1–58, which recapitulated the synergism between the parental compounds in high-risk and chemoresistant AML cells. Both PL and HDACi components, either in combination or in hybrid molecules, are essential for inducing

  哌隆定（PL）和HDAC抑制剂（HDACi）协同增效的抗白血病相互作用SAHA（Vorinostat）提供了令人信服的原理来构建PL-HDACi杂种，例如1 – 58，概述了高亲和力中亲本化合物之间的协同作用。风险和化学耐药性AML细胞。PL和HDACi成分（无论是组合分子还是杂合分子）对于诱导显着的DNA损伤和细胞凋亡都是必不可少的。将C2-氯取代基引入1 – 58可以产生3 – 35的细胞毒性，但在非癌性MCF-10A细胞中的选择性降低；消除获得的PL的C7–C8烯烃3 – 31 /3 – 98个支架在AML中仍比PL或SAHA更具活性，并且对MCF-10A细胞具有很好的耐受性。HDACi功能对于调节DNA修复和凋亡相关蛋白的表达至关重要。总的来说，PL和SAHA杂种是有效的多功能抗AML药物，部分地通过干扰细胞GSH防御，抑制DNA修复和促存活蛋白的表达以及诱导促凋亡蛋白的表达而发挥作用。
• [EN] PROSTAGLANDIN RECEPTOR EP2 ANTAGONISTS, DERIVATIVES, COMPOSITIONS, AND USES RELATED THERETO<br/>[FR] ANTAGONISTES DU RÉCEPTEUR EP2 DES PROSTAGLANDINES, DÉRIVÉS, COMPOSITIONS ET UTILISATIONS ASSOCIÉS
  申请人：UNIV EMORY

  公开号：WO2015167825A1

  公开（公告）日：2015-11-05

  The disclosure relates to Prostaglandin receptor EP2 antagonists, derivatives, compositions, and methods related thereto. In certain embodiments, the disclosure relates to methods of treating or preventing conditions and diseases in which EP2 receptor activation has a physiological role, such as but not limited to, brain injury, inflammatory diseases, neuroinflamation after a seizure, pain, endometriosis, cancer, rheumatoid arthritis, skin inflammation, vascular inflammation, colitis, and neurological disorders by administering a pharmaceutical composition comprising a compound disclosed herein to a subject in need thereof.

  该披露涉及前列腺素受体EP2拮抗剂，衍生物，组合物以及相关方法。在某些实施例中，该披露涉及治疗或预防EP2受体激活在生理作用中起作用的疾病和疾病的方法，例如但不限于脑损伤，炎症性疾病，癫痫后的神经炎症，疼痛，子宫内膜异位症，癌症，类风湿性关节炎，皮肤炎症，血管炎症，结肠炎和神经系统疾病，通过向需要的受试者给予包含本文所披露的化合物的药物组合物进行治疗。
• CONVENIENT MICROWAVE ASSISTED SYNTHESIS OF NATURALLY OCCURRING METHYL (<i>E</i>)-CINNAMATES
  作者：Rajesh P. Mahajan、Shamkant L. Patil、Raghao S. Mali

  DOI：10.1080/00304940509354962

  日期：2005.6

  ASSISTED SYNTHESIS OF NATURALLY OCCUR-RING METHYL (E)-CINNAMATESSubmitted by Rajesh P. Mahajan, Shamkant L. Patil* and Raghao S. Mali*(12/15/04)School of Chemical Sciences, North Maharashtra UniversityJalgaon - 425 001, INDIAe-mail: [e-mail]; Fax No. + (91) 0257 2258403A large number of methyl cinnamates have been isolated from various plant sources.Thus, the parent methyl (E)-cinnamate

  Rajesh P. Mahajan、Shamkant L. Patil* 和 Raghao S. Mali* (12/15/04) 化学科学学院，北马哈拉施特拉大学 -14J500 提交的自然发生的环甲基 (E)-肉桂的方便的微波辅助合成, 印度电子邮箱：[e-mail]；Fax No. + (91) 0257 2258403大量的肉桂酸甲酯已从各种植物来源中分离出来，从而分离出母体（E）肉桂酸甲酯（3a）
• Asymmetric Biomimetic Oxidations of Phenols: The Mechanism of the Diastereo- and Enantioselective Synthesis of Thomasidioic Acid
  作者：Luca Zoia、Maurizio Bruschi、Marco Orlandi、Eeva-Liisa Tolppa、Bruno Rindone

  DOI：10.3390/molecules13010129

  日期：——

  Enantiopure chiral amidic derivatives of sinapic acid were oxidised withhydrogen peroxide using horseradish peroxidase (HRP) as the catalyst to give thearyltetraline dilignol thomasidioic acid. Trans-diastereoselectivity and enantioselectivity inthe formation of thomasidioic acid was observed. Computational methods show that theenantioselectivity is controlled by the β-β oxidative coupling step, while thediastereoselectivity is controlled by the stability of the reactive conformation of theintermediate quinomethide.

  纯对映体的手性酰胺类芥子酸衍生物在辣根过氧化物酶（HRP）催化下，通过过氧化氢氧化生成芳基四氢化茚二联木脂酸托马斯二酸。在托马斯二酸的形成过程中观察到了反式非对映选择性和对映选择性。计算方法表明，对映选择性由β-β氧化偶联步骤控制，而非对映选择性则由中间体醌甲烷的反应构象的稳定性控制。