Dimethyl 2-[(4-hydroxy-3-methoxyphenyl)methylidene]butanedioate | 190004-89-8

• 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: Dimethyl 2-[(4-hydroxy-3-methoxyphenyl)methylidene]butanedioate
• 英文别名: dimethyl 2-[(4-hydroxy-3-methoxyphenyl)methylidene]butanedioate
• CAS: 190004-89-8
• 化学式: C₁₄H₁₆O₆
• 分子量: 280.277
• InChiKey: GWIHOXIGTZJTAM-UHFFFAOYSA-N

物化性质

• 沸点：
  429.9±45.0 °C(Predicted)
• 密度：
  1.242±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  82.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Dimethyl 2-[(4-hydroxy-3-methoxyphenyl)methylidene]butanedioate 在 lithium aluminium tetrahydride 、 硫酸 、 palladium 10% on activated carbon 、 氢气 、 lithium 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 97.0h， 生成 (+)-开环异落叶松树脂酚
  参考文献：
  名称：

  Synthesis and evaluation of cytotoxic effects of hanultarin and its derivatives

  摘要：

  One of the known cytotoxic lignans is (-)-1-O-feruloyl-secoisolariciresinol designated as hanultarin, which was isolated from the seeds of Trichosanthes kirilowii. In this Letter, we described the first synthesis of 1-O-feruloyl-secoisolariciresinol, 1,4-O-diferuloyl-secoisolariceresinol and their analogues. The cytotoxicities of these compounds were evaluated against several cancer cell lines. Interestingly, we found that the feruloyl diester derivative of secoisolariciresinol was the most active cytotoxic compound against all the cancer cells tested in this experiment. The IC(50) values of the 1,4-O-diferuloyl-secoisolariceresinol were in the range of 7.1-9.8 mu M except one cell line. In considering that both ferulic acid and secoisolariciresinol are commonly found in many plants and have no cytotoxicity, this finding is remarkable in that simple covalent bonds between the ferulic acid and secoisolariciresinol cause a cytotoxic effect. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.09.014
• 作为产物：
  描述：

  香草醛 、 丁二酸二甲酯 在 硫酸 、 lithium 作用下， 以 甲醇 为溶剂， 反应 72.0h， 生成 Dimethyl 2-[(4-hydroxy-3-methoxyphenyl)methylidene]butanedioate
  参考文献：
  名称：

  Synthesis and evaluation of cytotoxic effects of hanultarin and its derivatives

  摘要：

  One of the known cytotoxic lignans is (-)-1-O-feruloyl-secoisolariciresinol designated as hanultarin, which was isolated from the seeds of Trichosanthes kirilowii. In this Letter, we described the first synthesis of 1-O-feruloyl-secoisolariciresinol, 1,4-O-diferuloyl-secoisolariceresinol and their analogues. The cytotoxicities of these compounds were evaluated against several cancer cell lines. Interestingly, we found that the feruloyl diester derivative of secoisolariciresinol was the most active cytotoxic compound against all the cancer cells tested in this experiment. The IC(50) values of the 1,4-O-diferuloyl-secoisolariceresinol were in the range of 7.1-9.8 mu M except one cell line. In considering that both ferulic acid and secoisolariciresinol are commonly found in many plants and have no cytotoxicity, this finding is remarkable in that simple covalent bonds between the ferulic acid and secoisolariciresinol cause a cytotoxic effect. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.09.014

文献信息

• [EN] PREPARATION OF (S,S)-SECOISOLARICIRESINOL DIGLUCOSIDE AND (R,R)-SECOISOLARICIRESINOL DIGLUCOSIDE<br/>[FR] PRÉPARATION DE (S,S)-SÉCOISOLARICIRÉSINOL DIGLUCOSIDE ET DE (R,R)-SÉCOISOLARICIRÉSINOL DIGLUCOSIDE
  申请人：UNIV PENNSYLVANIA

  公开号：WO2014200964A1

  公开（公告）日：2014-12-18

  The invention relates to processes for preparing (S,S)-secoisolariciresinol diglucoside and (R,R)-secoisolariciresinol diglucoside and compositions comprising the same.

  该发明涉及制备（S，S）-丝氨酸木脂糖苷和（R，R）-丝氨酸木脂糖苷的过程以及包含它们的组合物。
• Synthesis and antioxidant evaluation of (S,S)- and (R,R)-secoisolariciresinol diglucosides (SDGs)
  作者：Om P. Mishra、Nicholas Simmons、Sonia Tyagi、Ralph Pietrofesa、Vladimir V. Shuvaev、Roman A. Valiulin、Philipp Heretsch、K.C. Nicolaou、Melpo Christofidou-Solomidou

  DOI：10.1016/j.bmcl.2013.07.062

  日期：2013.10

  Secoisolariciresinol diglucosides (SDGs) (S,S)-SDG-1 (major isomer in flaxseed) and (R,R)-SDG-2 (minor isomer in flaxseed) were synthesized from vanillin via secoisolariciresinol (6) and glucosyl donor 7 through a concise route that involved chromatographic separation of diastereomeric diglucoside derivatives (S,S)-8 and (R,R)-9. Synthetic (S,S)-SDG-1 and (R, R)-SDG-2 exhibited potent antioxidant properties (EC50 = 292.17 +/- 27.71 mu M and 331.94 +/- 21.21 mu M, respectively), which compared well with that of natural (S,S)-SDG-1 (EC50 = 275.24 +/- 13.15 mu M). These values are significantly lower than those of ascorbic acid (EC50 = 1129.32 +/- 88.79 mu M) and a-tocopherol (EC50 = 944.62 +/- 148.00 mu M). Compounds (S,S)SDG-1 and (R, R)-SDG-2 also demonstrated powerful scavenging activities against hydroxyl [natural (S,S)-SDG-1: 3.68 +/- 0.27; synthetic (S,S)-SDG-1: 2.09 +/- 0.16; synthetic (R,R)-SDG-2: 1.96 +/- 0.27], peroxyl [natural (S,S)-SDG-1: 2.55 +/- 0.11; synthetic (S,S)-SDG-1: 2.20 +/- 0.10; synthetic (R,R)-SDG-2: 3.03 +/- 0.04] and DPPH [natural (S, S)-SDG-1: EC50 = 83.94 +/- 2.80 mu M; synthetic (S, S)-SDG-1: EC50 = 157.54 +/- 21.30 lM; synthetic (R, R)-SDG-2: EC50 = 123.63 +/- 8.67 mu M] radicals. These results confirm previous studies with naturally occurring (S,S)-SDG-1 and establish both (S, S)-SDG-1 and (R,R)-SDG-2 as potent antioxidants and free radical scavengers for potential in vivo use. (C) 2013 Elsevier Ltd. All rights reserved.
• Synthesis and evaluation of cytotoxic effects of hanultarin and its derivatives
  作者：Eunyoung Lee、V.S. Jamal Ahamed、Mahto Sanjeev Kumar、Seog Woo Rhee、Surk-Sik Moon、In Seok Hong

  DOI：10.1016/j.bmcl.2011.09.014

  日期：2011.11

  One of the known cytotoxic lignans is (-)-1-O-feruloyl-secoisolariciresinol designated as hanultarin, which was isolated from the seeds of Trichosanthes kirilowii. In this Letter, we described the first synthesis of 1-O-feruloyl-secoisolariciresinol, 1,4-O-diferuloyl-secoisolariceresinol and their analogues. The cytotoxicities of these compounds were evaluated against several cancer cell lines. Interestingly, we found that the feruloyl diester derivative of secoisolariciresinol was the most active cytotoxic compound against all the cancer cells tested in this experiment. The IC(50) values of the 1,4-O-diferuloyl-secoisolariceresinol were in the range of 7.1-9.8 mu M except one cell line. In considering that both ferulic acid and secoisolariciresinol are commonly found in many plants and have no cytotoxicity, this finding is remarkable in that simple covalent bonds between the ferulic acid and secoisolariciresinol cause a cytotoxic effect. (C) 2011 Elsevier Ltd. All rights reserved.