5-[(3-Hydroxy-4-methoxyphenyl)methyl]oxolan-2-one | 848653-51-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 5-[(3-Hydroxy-4-methoxyphenyl)methyl]oxolan-2-one
• CAS: 848653-51-0
• 化学式: C₁₂H₁₄O₄
• 分子量: 222.241
• InChiKey: CEZQHDADSGTTOP-UHFFFAOYSA-N

物化性质

• 沸点：
  430.0±25.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

ADMET

代谢

5-(3p,4p-二羟基苯基)-γ-戊内酯-4p-O-甲基已知的人类代谢物包括5-(3',4'-二羟基苯基)-γ-戊内酯-4'-O-甲基-3'-O-葡萄糖苷酸酯。

5-(3p,4p-Dihydroxyphenyl)-gamma-valerolactone-4p-O-methyl has known human metabolites that include 5-(3',4'-Dihydroxyphenyl)-gamma-valerolactone-4'-O-methyl-3'-O-glucuronide.

来源:NORMAN Suspect List Exchange

反应信息

• 作为反应物：
  描述：

  5-[(3-Hydroxy-4-methoxyphenyl)methyl]oxolan-2-one 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 以34%的产率得到5-[(3,4-二羟基苯基)甲基]二氢-2(3H)-呋喃酮
  参考文献：
  名称：

  Synthesis and biological activity of the tea catechin metabolites, M4 and M6 and their methoxy-derivatives

  摘要：

  Syntheses are reported for metabolites M4 (1) and M6 (2) of the green tea polyphenols epicatechin (EC) and epigallocatechin (EGC) and their gallate derivatives. Several methoxy-derivatives of 1 and 2 were also prepared. Compounds 1 and 2 were evaluated for growth inhibitory activity against a panel of immortalized and malignant human cell lines with 1 being the more active compound. The possible antiinflammatory activity of 1 and its trimethoxy derivative was also evaluated. Neither compound inhibited the release of arachidonic acid, although 1 inhibited NO production by 50% at 20 muM. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.12.070
• 作为产物：
  描述：

  4-戊烯酸甲酯 在 palladium diacetate 、 氢氧化钾 、 copper(II) sulfate 、 三苯基膦 、 silver carbonate 作用下， 以 甲醇 、 乙腈 、 苯 为溶剂， 生成 5-[(3-Hydroxy-4-methoxyphenyl)methyl]oxolan-2-one
  参考文献：
  名称：

  Synthesis and biological activity of the tea catechin metabolites, M4 and M6 and their methoxy-derivatives

  摘要：

  Syntheses are reported for metabolites M4 (1) and M6 (2) of the green tea polyphenols epicatechin (EC) and epigallocatechin (EGC) and their gallate derivatives. Several methoxy-derivatives of 1 and 2 were also prepared. Compounds 1 and 2 were evaluated for growth inhibitory activity against a panel of immortalized and malignant human cell lines with 1 being the more active compound. The possible antiinflammatory activity of 1 and its trimethoxy derivative was also evaluated. Neither compound inhibited the release of arachidonic acid, although 1 inhibited NO production by 50% at 20 muM. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.12.070