2,4,5-trichlorophenyl-β-D(6-O-malonyl)-glucopyranoside

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,4,5-trichlorophenyl-β-D(6-O-malonyl)-glucopyranoside
• 英文别名: 3-oxo-3-[[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-(2,4,5-trichlorophenoxy)oxan-2-yl]methoxy]propanoic acid
• 化学式: C₁₅H₁₅Cl₃O₉
• 分子量: 445.638
• InChiKey: UBTLYZOQZLKASW-SWMGHYKJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  143
• 氢给体数：
  4
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  2,4,5-三氯苯酚 在 sodium hydroxide 、 异氰酸叔丁酯 、 sodium methylate 作用下， 以 甲醇 、 丙酮 、 乙腈 为溶剂， 反应 1.0h， 生成 2,4,5-trichlorophenyl-β-D(6-O-malonyl)-glucopyranoside
  参考文献：
  名称：

  GLYCOSIDATION OF CHLOROPHENOLS BY LEMNA MINOR

  摘要：

  AbstractMetabolic fate of xenobiotics in plant tissues has an important role in the ultimate fate of these compounds in natural and engineered systems. Chlorophenols are an important class of xenobiotics used in a variety of biocides and have been shown to be resistant to microbial degradation. Three chlorophenyl glycosides were extracted from tissues ofLemna minorexposed to 2,4‐dichlorophenol (DCP). The products were identified as 2,4‐dichlorophenyl‐β‐D‐glucopyranoside (DCPG), 2,4‐dichlorophenyl‐β‐D‐(6‐O‐malonyl)‐glucopyranoside (DCPMG) and 2,4‐dichlorophenyl‐β‐D‐glucopyranosyl‐(6→1)‐β‐D‐apiofuranoside (DCPAG). Identification was based on reverse phase retention (C18), electrospray mass spectra collected in negative and positive mode (ESI‐NEG and ESI‐POS, respectively), and nuclear magnetic resonance (NMR) spectra comparisons to reference materials synthesized in the laboratory. Liquid chromatography‐mass spectrometry (LC‐MS) analysis of plants exposed to 2,4,5‐trichlorophenol (TCP) formed analogous compounds: 2,4,5‐trichlorophenyl‐β‐D‐glucopyranoside (TCPG), 2,4,5‐trichlorophenyl‐β‐D‐(6‐O‐malonyl)‐glucopyranoside (TCPMG) and 2,4,5‐trichlorophenyl‐β‐D‐glucopyranosyl‐(6→1)‐β‐D‐apiofuranoside (TCPAG). Enzyme catalyzed hydrolysis with β‐glucosidase was ineffective in releasing the β‐glucosides with chemical modifications at C6. Presence of these glucoconjugates confirmed thatL. minorwas capable of xenobiotic uptake and transformation. Identification of these products suggested that chlorophenols were incorporated into vacuoles and cell walls ofL. minor.

  DOI：

  10.1897/02-649

文献信息

• GLYCOSIDATION OF CHLOROPHENOLS BY LEMNA MINOR
  作者：James A. Day、F. Michael Saunders

  DOI：10.1897/02-649

  日期：——

  AbstractMetabolic fate of xenobiotics in plant tissues has an important role in the ultimate fate of these compounds in natural and engineered systems. Chlorophenols are an important class of xenobiotics used in a variety of biocides and have been shown to be resistant to microbial degradation. Three chlorophenyl glycosides were extracted from tissues ofLemna minorexposed to 2,4‐dichlorophenol (DCP). The products were identified as 2,4‐dichlorophenyl‐β‐D‐glucopyranoside (DCPG), 2,4‐dichlorophenyl‐β‐D‐(6‐O‐malonyl)‐glucopyranoside (DCPMG) and 2,4‐dichlorophenyl‐β‐D‐glucopyranosyl‐(6→1)‐β‐D‐apiofuranoside (DCPAG). Identification was based on reverse phase retention (C18), electrospray mass spectra collected in negative and positive mode (ESI‐NEG and ESI‐POS, respectively), and nuclear magnetic resonance (NMR) spectra comparisons to reference materials synthesized in the laboratory. Liquid chromatography‐mass spectrometry (LC‐MS) analysis of plants exposed to 2,4,5‐trichlorophenol (TCP) formed analogous compounds: 2,4,5‐trichlorophenyl‐β‐D‐glucopyranoside (TCPG), 2,4,5‐trichlorophenyl‐β‐D‐(6‐O‐malonyl)‐glucopyranoside (TCPMG) and 2,4,5‐trichlorophenyl‐β‐D‐glucopyranosyl‐(6→1)‐β‐D‐apiofuranoside (TCPAG). Enzyme catalyzed hydrolysis with β‐glucosidase was ineffective in releasing the β‐glucosides with chemical modifications at C6. Presence of these glucoconjugates confirmed thatL. minorwas capable of xenobiotic uptake and transformation. Identification of these products suggested that chlorophenols were incorporated into vacuoles and cell walls ofL. minor.