(E)-1-hydroxy-4-(4-hydroxy-3-methoxyphenyl)-but-3-en-2-one | 336784-86-2

• 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: (E)-1-hydroxy-4-(4-hydroxy-3-methoxyphenyl)-but-3-en-2-one
• 英文别名: (E)-1-hydroxy-4-(4-hydroxy-3-methoxyphenyl)but-3-en-2-one
• CAS: 336784-86-2
• 化学式: C₁₁H₁₂O₄
• 分子量: 208.214
• InChiKey: NPMHZTTYMXAUIV-DUXPYHPUSA-N

物化性质

• 沸点：
  394.6±37.0 °C(Predicted)
• 密度：
  1.269±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-1-hydroxy-4-(4-hydroxy-3-methoxyphenyl)-but-3-en-2-one 以100%的产率得到(E)-1-hydroxy-4-(3-methoxy-4-trimethylsilyloxyphenyl)but-3-en-2-one
  参考文献：
  名称：

  Pharmaceutical compositions useful in prevention and treatment of beta-Amyloid protein-induced disease

  摘要：

  这项发明提供了用于治疗β-淀粉样蛋白诱导疾病的方法，以及用于相同目的的药物组合物和化合物，以及利用这些化合物制造治疗该疾病的药物的用途。更具体地说，该发明涉及利用从姜黄、银杏和姜中分离的天然产物化合物以及其合成化学类似物，用于治疗β-淀粉样蛋白诱导的疾病。

  公开号：

  US06887898B1
• 作为产物：
  描述：

  3-甲氧基-4-[(四氢-2H-吡喃-2-基)氧基]苯甲醛 在 4-甲基苯磺酸吡啶 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 1.0h， 生成 (E)-1-hydroxy-4-(4-hydroxy-3-methoxyphenyl)-but-3-en-2-one
  参考文献：
  名称：

  Total synthesis of calebin-A, preparation of its analogues, and their neuronal cell protectivity against β-amyloid insult

  摘要：

  A total synthesis of Calebin-A (1), a novel curcuminoid isolated from turmeric (Curcuma longa, Zingiberaceae) that has been demonstrated to protect neuronal cells from beta -amyloid insult, was successfully achieved in four steps. Elaborating on this synthetic route. 13 analogues were prepared for a structure-activity relationship (SAR) study. It was found that the parent compound 1 and derivatives 21, 28, and 30 protect PC12 rat pheocromocytoma and IMR-32 human neuroblastoma cells from beta -amyloid(25-35) insult. These results suggest that hydroxy group at para-position is most critical for the expression of biological activity. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00489-9

文献信息

• SYNTHESIS OF CALEBIN-A AND ITS BIOLOGICALLY ACTIVE ANALOGS
  申请人：Majeed Muhammed

  公开号：US20160002141A1

  公开（公告）日：2016-01-07

  Disclosed is a simple, economical, industrially scalable green synthetic process for Calebin-A and its biologically active analogs.

  本发明公开了一种简单、经济、工业可扩展的绿色合成过程，用于合成Calebin-A及其生物活性类似物。
• Contribution of Hydroxycinnamic Acids to Color Formation in Nonenzymatic Browning Reactions with Key Maillard Reaction Intermediates
  作者：Leon Valentin Bork、Nicolas Proksch、Sascha Rohn、Clemens Kanzler

  DOI：10.1021/acs.jafc.3c07168

  日期：2024.1.24

  was to characterize early reactions, underlying the formation of phenol-containing melanoidins. For this purpose, binary model systems of the prominent phenolic compounds caffeic acid and ferulic acid combined with α-dicarbonyl compounds typically formed in the Maillard reaction such as glyoxal, methylglyoxal, and diacetyl were analyzed after heat treatment. High-resolution mass spectrometry revealed

  美拉德反应是食品加工的重要组成部分，涉及大量复杂的反应途径，最终产生高分子量着色剂。迄今为止，研究主要集中在碳水化合物和氨基化合物的转化上，但详细阐述酚类化合物对有色最终产品形成的贡献的文献仍然很少。本研究的目的是表征含酚类黑素形成的早期反应。为此，在热处理后对主要酚类化合物咖啡酸和阿魏酸与通常在美拉德反应中形成的α-二羰基化合物（例如乙二醛、甲基乙二醛和二乙酰）结合的二元模型系统进行了分析。高分辨率质谱分析表明，脱羧、芳香族亲电取代和亲核加成是产生有色异质低聚物的重要反应步骤。芳香体系中具有高电子密度的酚类化合物和带有醛官能团的α-二羰基化合物有利于聚合。
• Synthesis of Calebin-A and its biologically active analogs
  申请人：Majeed, Muhammed

  公开号：EP2963007A1

  公开（公告）日：2016-01-06

  Disclosed is a simple, economical, industrially scalable green synthetic process for Calebin-A and its biologically active analogs.

  所公开的是一种简单、经济、可工业化扩展的 Calebin-A 及其生物活性类似物的绿色合成工艺。
• Synergistic pharmaceutical compositions useful in prevention and treatment of beta-amyloid protein-induced disease
  申请人：Kim S. H. L. Darrick

  公开号：US20070003641A1

  公开（公告）日：2007-01-04

  Disclosed are combinations of natural and synthetic turmeric, ginger, ginko biloba, sage, and rosemary compounds suitable for treatment of beta-amyloid-disease induced disease that have synergistic anti-βA peptide effects when members of the five groups of compounds are combined. Suitable members of the compounds include both natural compounds derived from extracts of each of Curcuma sp., Zingiber sp., Ginkgo biloba, Salvia sp., or Rosmarinus sp. as well as synthetic homologues and analogues of such natural compounds. Sage and rosemary derived compounds suitable alone for treatment of beta-amyloid induced disease is also described.
• US7728043B2
  申请人：——

  公开号：US7728043B2

  公开（公告）日：2010-06-01