3-{3-ethoxy-2-β-D-glucopyranosyloxy-5-[(isopropoxycarbonyl)amino]phenylthio}-2-hydroxypropionic acid

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-{3-ethoxy-2-β-D-glucopyranosyloxy-5-[(isopropoxycarbonyl)amino]phenylthio}-2-hydroxypropionic acid
• 英文别名: 3-[3-ethoxy-5-(propan-2-yloxycarbonylamino)-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]sulfanyl-2-hydroxypropanoic acid
• 化学式: C₂₁H₃₁NO₁₂S
• 分子量: 521.543
• InChiKey: QWGWFSLNTRFRRJ-OJFAPVQASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  35
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  230
• 氢给体数：
  7
• 氢受体数：
  13

反应信息

• 作为产物：
  描述：

  4-硝基儿茶酚 在 palladium on activated charcoal lead(IV) acetate 、 氢氧化钾 、 sodium hydroxide 、 氢气 、 sodium hydride 、 N,N-二甲基苯胺 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 乙二醇甲醚 、 N,N-二甲基甲酰胺 为溶剂， 生成 3-{3-ethoxy-2-β-D-glucopyranosyloxy-5-[(isopropoxycarbonyl)amino]phenylthio}-2-hydroxypropionic acid
  参考文献：
  名称：

  Metabolism of Fungicide Diethofencarb in Grape (Vitis vinifera L.):  Definitive Identification of Thiolactic Acid Conjugated Metabolites

  摘要：

  The metabolic fate of diethofencarb (isopropyl 3,4-diethoxycarbanilate) separately labeled with C-14 at the phenyl ring and 2-position of the isopropyl moiety was studied in grape (Vitis vinifera L.). The acetonitrile solution of C-14-diethofencarb at a rate of 500 g a.i. ha(-1) was once applied topically to fruits or leaves at the maturity stage of fruits (PHI 35 days), and the plants were grown in the greenhouse until harvest. In the grape plants, diethofencarb was scarcely translocated to the untreated portion and was degraded more in the fruit as compared to the leaf. For the fruit, diethofencarb primary underwent O-deethylation at the 4-position of the phenyl ring to form the phenolic derivative, isopropyl 3-ethoxy-4-hydroxycarbanilate (0.9% of the total radioactive residue, TRR). This metabolite was successively transformed via conjugation with glucose at the phenolic hydroxy group (8.1-18.1% TRR) or with thiolactic acid at the 5-position of the phenyl ring (1.5-1.7% TRR). The thiolactic acid conjugate was further metabolized mainly to two different types of glucose conjugates at the 4-position of the phenyl ring (8.7-13.5% TRR) and the hydroxy group in the thiolactic acid moiety (6.4-7.3% TRR), as evidenced by H-1 NMR and atmospheric pressure chemical ionization-liquid chromatography-mass spectrometry together with cochromatographies with synthetic standards.

  DOI：

  10.1021/jf034367+

文献信息

• Metabolism of Fungicide Diethofencarb in Grape (<i>Vitis vinifera </i>L.):  Definitive Identification of Thiolactic Acid Conjugated Metabolites
  作者：Takuo Fujisawa、Keiko Ichise-Shibuya、Toshiyuki Katagi、Luis O. Ruzo、Yoshiyuki Takimoto

  DOI：10.1021/jf034367+

  日期：2003.8.1

  The metabolic fate of diethofencarb (isopropyl 3,4-diethoxycarbanilate) separately labeled with C-14 at the phenyl ring and 2-position of the isopropyl moiety was studied in grape (Vitis vinifera L.). The acetonitrile solution of C-14-diethofencarb at a rate of 500 g a.i. ha(-1) was once applied topically to fruits or leaves at the maturity stage of fruits (PHI 35 days), and the plants were grown in the greenhouse until harvest. In the grape plants, diethofencarb was scarcely translocated to the untreated portion and was degraded more in the fruit as compared to the leaf. For the fruit, diethofencarb primary underwent O-deethylation at the 4-position of the phenyl ring to form the phenolic derivative, isopropyl 3-ethoxy-4-hydroxycarbanilate (0.9% of the total radioactive residue, TRR). This metabolite was successively transformed via conjugation with glucose at the phenolic hydroxy group (8.1-18.1% TRR) or with thiolactic acid at the 5-position of the phenyl ring (1.5-1.7% TRR). The thiolactic acid conjugate was further metabolized mainly to two different types of glucose conjugates at the 4-position of the phenyl ring (8.7-13.5% TRR) and the hydroxy group in the thiolactic acid moiety (6.4-7.3% TRR), as evidenced by H-1 NMR and atmospheric pressure chemical ionization-liquid chromatography-mass spectrometry together with cochromatographies with synthetic standards.