O-β-D-glucopyranosyl-2,4-dichlorophenol | 28217-30-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: O-β-D-glucopyranosyl-2,4-dichlorophenol
• 英文别名: 2,4-dichlorophenol β-D-glucopyranoside；2,4-dichlorophenyl-β-D-glucopyranoside；(2,4-dichloro-phenyl)-β-D-glucopyranoside；(2,4-Dichlor-phenyl)-β-D-glucopyranosid；2,4-dichlorophenyl-β-D-glucoside；(2S,3R,4S,5S,6R)-2-(2,4-dichlorophenoxy)-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 28217-30-3
• 化学式: C₁₂H₁₄Cl₂O₆
• 分子量: 325.146
• InChiKey: FMLFENLCSTYAST-RMPHRYRLSA-N

物化性质

• 沸点：
  533.2±50.0 °C(Predicted)
• 密度：
  1.622±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  99.4
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  丙二酸 、 O-β-D-glucopyranosyl-2,4-dichlorophenol 在 异氰酸叔丁酯 作用下， 以 乙腈 为溶剂， 反应 1.0h， 生成 (6-O-malonyl)-O-β-D-glucopyranosyl-2,4-dichlorophenol
  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
• 作为产物：
  描述：

  2,4-二氯酚 在 sodium hydroxide 、 sodium methylate 作用下， 以 甲醇 、 丙酮 为溶剂， 反应 1.5h， 生成 O-β-D-glucopyranosyl-2,4-dichlorophenol
  参考文献：
  名称：

  Toxicity and metabolism of 2,4-dichlorophenol by the aquatic angiospermLemna gibba

  摘要：

  AbstractThe toxicity and metabolism of 2,4‐dichlorophenol, with regard to the aquatic macrophyte Lemna gibba (duckweed), have been studied Toxicity is described in terms of the effect of 2,4‐dichlorophenol (2,4‐DCP) on the vegetative reproduction of duckweed over a 10‐d growth period, the EC10 and EC50 were 2.5 and 9 2 μM, respectively. Metabolism of 2,4‐dichlorophenol was monitored by incubation of the plants with radiolabeled substrate, and periodic sampling and analysis by reversed‐phase HPLC of the plant growth medium Depending on the growth conditions, up to 95% of the 2,4‐DCP was metabolized over a 6‐d growth period. To analyze the metabolites, the plants were grown in the presence of sublethal concentrations of [U‐14C]‐2,4‐DCP. The growth medium was lyophihzed and then mixed with the plants, extracted, and analyzed using reversed‐phase HPLC, followed by scintillation counting of the fractions The major metabolite was isolated and identified as 2,4‐dichlo‐rophenyl‐β‐D‐glucopyranoside by high‐field NMR and MS. The structure of the metabolite was confirmed by synthesis and by enzymatic cleavage of the β‐glucosidic linkage to afford 2,4‐DCP. An important consequence of conjugate formation is the masking of the presence of 2,4‐DCP to the usual analytical techniques used for its detection and quantitation. This finding is probably applicable to other contaminants and organisms.

  DOI：

  10.1002/etc.5620130217

文献信息

• Über eine neue Synthese von Phenolglykosiden
  作者：Karl W. Rosenmund、Eckart Güssow

  DOI：10.1002/ardp.19542870109

  日期：——
• Synthetic plant hormones. Part II. Some glucosides and aldehydes
  作者：M. H. Maguire、G. Shaw

  DOI：10.1039/jr9540003669

  日期：——
• US5208151A
  申请人：——

  公开号：US5208151A

  公开（公告）日：1993-05-04
• Toxicity and metabolism of 2,4-dichlorophenol by the aquatic angiosperm<i>Lemna gibba</i>
  作者：Harry E. Ensley、John T. Barber、Michael A. Polito、Ana I. Oliver

  DOI：10.1002/etc.5620130217

  日期：1994.2

  AbstractThe toxicity and metabolism of 2,4‐dichlorophenol, with regard to the aquatic macrophyte Lemna gibba (duckweed), have been studied Toxicity is described in terms of the effect of 2,4‐dichlorophenol (2,4‐DCP) on the vegetative reproduction of duckweed over a 10‐d growth period, the EC10 and EC50 were 2.5 and 9 2 μM, respectively. Metabolism of 2,4‐dichlorophenol was monitored by incubation of the plants with radiolabeled substrate, and periodic sampling and analysis by reversed‐phase HPLC of the plant growth medium Depending on the growth conditions, up to 95% of the 2,4‐DCP was metabolized over a 6‐d growth period. To analyze the metabolites, the plants were grown in the presence of sublethal concentrations of [U‐14C]‐2,4‐DCP. The growth medium was lyophihzed and then mixed with the plants, extracted, and analyzed using reversed‐phase HPLC, followed by scintillation counting of the fractions The major metabolite was isolated and identified as 2,4‐dichlo‐rophenyl‐β‐D‐glucopyranoside by high‐field NMR and MS. The structure of the metabolite was confirmed by synthesis and by enzymatic cleavage of the β‐glucosidic linkage to afford 2,4‐DCP. An important consequence of conjugate formation is the masking of the presence of 2,4‐DCP to the usual analytical techniques used for its detection and quantitation. This finding is probably applicable to other contaminants and organisms.
• 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.