4-(4-hydroxy-3-methoxyphenyl)-2-oxo-3-butenyl 3-(4-hydroxyphenyl)-propenoate

• 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: 4-(4-hydroxy-3-methoxyphenyl)-2-oxo-3-butenyl 3-(4-hydroxyphenyl)-propenoate
• 英文别名: feruloylmethyl 4-hydroxycinnamate；demethoxycalebin-A1；[(E)-4-(4-hydroxy-3-methoxyphenyl)-2-oxobut-3-enyl] (E)-3-(4-hydroxyphenyl)prop-2-enoate
• 化学式: C₂₀H₁₈O₆
• 分子量: 354.359
• InChiKey: BJZHFDWMVXWBJF-WOARVNPXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  93.1
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  3-甲氧基-4-[(四氢-2H-吡喃-2-基)氧基]苯甲醛 在 4-二甲氨基吡啶 、 4-(dimethylamino)pyridine hydrochloride 、 4-甲基苯磺酸吡啶 、 potassium carbonate 、 N,N'-二环己基碳二亚胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 氯仿 为溶剂， 反应 1.0h， 生成 4-(4-hydroxy-3-methoxyphenyl)-2-oxo-3-butenyl 3-(4-hydroxyphenyl)-propenoate
  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。
• 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。
• POLYMERIC NANOPARTICLES COMPRISING TURMERIC
  申请人：XEROX CORPORATION

  公开号：US20150232642A1

  公开（公告）日：2015-08-20

  Disclosed herein are latex emulsion compositions comprising water, turmeric, at least one surfactant, and at least one organic monomer, wherein the latex emulsion composition has an average particle size of less than about 250 nm. Also disclosed herein are processes for preparing a latex emulsion composition comprising water, turmeric, at least one surfactant, and at least one organic monomer, wherein the latex emulsion composition has an average particle size of less than about 250 nm. Further disclosed herein is the use of turmeric-containing latex emulsion compositions as paints, inks, toners, cosmetics, health aids, beauty aids, foods, and coatings.
• US9365486B2
  申请人：——

  公开号：US9365486B2

  公开（公告）日：2016-06-14
• Total synthesis of calebin-A, preparation of its analogues, and their neuronal cell protectivity against β-amyloid insult
  作者：Darrick S.H.L Kim、Jin Yung Kim

  DOI：10.1016/s0960-894x(01)00489-9

  日期：2001.9

  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.