2,5-dibromoprotocatechualdehyde | 70625-28-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,5-dibromoprotocatechualdehyde
• 英文别名: 2,5-Dibrom-brenzcatechinaldehyd；2,5-Dibromo-3,4-dihydroxybenzaldehyde
• CAS: 70625-28-4
• 化学式: C₇H₄Br₂O₃
• mdl: MFCD02060091
• 分子量: 295.915
• InChiKey: RMVZWWRDAIPUJH-UHFFFAOYSA-N

物化性质

• 沸点：
  296.4±35.0 °C(Predicted)
• 密度：
  2.270±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,5-dibromoprotocatechualdehyde 生成 2,5-dibromoveratraldehyde
  参考文献：
  名称：

  Lundgren,L. et al., Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1979, vol. 33, p. 105 - 108

  摘要：

  DOI：
• 作为产物：
  描述：

  3,4-二羟基苯甲醛 在 溴 作用下， 以 氯仿 为溶剂， 反应 18.0h， 生成 2,5-dibromoprotocatechualdehyde
  参考文献：
  名称：

  Metabolic analysis of the cinnamate/monolignol pathway in Carthamus tinctorius seeds by a stable-isotope-dilution method

  摘要：

  本研究通过使用稳定同位素稀释法建立了一个对肉桂酸/单木酚和木脂素途径进行综合代谢分析的系统。该系统成功应用于对红花胭脂树（Carthamus tinctorius cv. Round-leaved White）成熟种子中结合稳定同位素标记前体施用途径的表征。使用该技术获得的实验结果有力地表明了阿魏酸在植物木脂素生物合成中的中介作用。

  DOI：

  10.1039/b616705e

文献信息

• In<i>-</i>vitro Cytotoxic Activities of the Major Bromophenols of the Red Alga<i> Polysiphonia </i><i>l</i><i>anosa</i> and Some Novel Synthetic Isomers
  作者：Nagwa A. Shoeib、Michael C. Bibby、Gerald Blunden、Peter A. Linley、David J. Swaine、Richard T. Wheelhouse、Colin W. Wright

  DOI：10.1021/np0305268

  日期：2004.9.1

  Bioassay-guided fractionation was applied to the cytotoxic chloroform fraction of the red alga Polysiphonia lanosa, The major compounds of the most active fraction were identified using GLC-MS analysis as lanosol (1), methyl, ethyl, and n-propyl ethers of lanosol (1a, 1b, and 1c, respectively), and aldehyde of lanosol (2), although 1b appears to be an artifact arising during the fractionation procedure. These compounds and other known bromophenols were synthesized in addition to four novel isomers (3, 3a-c). The cytotoxic activities of all the synthetic compounds were determined against DLD-1 cells using the MTT assay. Compounds with IC50 < 20 mumol were also tested against HCT-116 cells. Compound 3c (2,5-dibromo-3,4-dihydroxybenzyl n-propyl ether) was the most active compound against both cell lines (IC50 = 1.72 and 0.80 mumol, respectively), and its effect on the cell cycle was studied using flow cytometry.
• Lundgren,L. et al., Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1979, vol. 33, p. 105 - 108
  作者：Lundgren,L. et al.

  DOI：——

  日期：——
• Metabolic analysis of the cinnamate/monolignol pathway in Carthamus tinctorius seeds by a stable-isotope-dilution method
  作者：Norikazu Sakakibara、Tomoyuki Nakatsubo、Shiro Suzuki、Daisuke Shibata、Mikio Shimada、Toshiaki Umezawa

  DOI：10.1039/b616705e

  日期：——

  The present study established a system for comprehensive metabolic analysis of the cinnamate/monolignol and lignan pathways by the use of a stable-isotope-dilution method. The system was successfully applied to characterization of the pathways in Carthamus tinctorius cv. Round-leaved White maturing seeds in combination with administration of stable-isotope-labelled precursors. Experimental results obtained using this technique strongly suggested the intermediacy of ferulic acid in lignan biosynthesis in the plant.

  本研究通过使用稳定同位素稀释法建立了一个对肉桂酸/单木酚和木脂素途径进行综合代谢分析的系统。该系统成功应用于对红花胭脂树（Carthamus tinctorius cv. Round-leaved White）成熟种子中结合稳定同位素标记前体施用途径的表征。使用该技术获得的实验结果有力地表明了阿魏酸在植物木脂素生物合成中的中介作用。