2-[2-(3-羟基-4-甲氧基苯基)乙基]-6-羟基苯甲酸 | 762260-06-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 中文名称: 2-[2-(3-羟基-4-甲氧基苯基)乙基]-6-羟基苯甲酸
• 英文名称: 2-[2-(3-hydroxy-4-methoxyphenyl)ethyl]-6-hydroxybenzoic acid
• 英文别名: 3,3'-dihydroxy-4'-methoxy-bibenzyl-2-carboxylic acid；3.3'-Dioxy-4'-methoxy-dibenzyl-carbonsaeure-(2)；Desoxyphyllodulcinsaeure；3,3'-Dihydroxy-4'-methoxy-bibenzyl-2-carbonsaeure；2-Hydroxy-6-[2-(3-hydroxy-4-methoxyphenyl)ethyl]benzoic acid
• CAS: 762260-06-0
• 化学式: C₁₆H₁₆O₅
• 分子量: 288.3
• InChiKey: FSYUBSAOKUAUCZ-UHFFFAOYSA-N

物化性质

• 熔点：
  142-145 °C
• 沸点：
  477.3±45.0 °C(Predicted)
• 密度：
  1.332±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  87
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-[2-(3-羟基-4-甲氧基苯基)乙基]-6-羟基苯甲酸 在 氢氧化钾 、 permanganate(VII) ion 作用下， 生成 3,4-二甲氧基苯丙酸
  参考文献：
  名称：

  Asahina; Asano, Chemische Berichte, 1929, vol. 62, p. 172,176

  摘要：

  DOI：
• 作为产物：
  描述：

  phyllodulcin 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以100%的产率得到2-[2-(3-羟基-4-甲氧基苯基)乙基]-6-羟基苯甲酸
  参考文献：
  名称：

  Metabolic Fate of Orally Administered Phyllodulcin in Rats

  摘要：

  Naturally occurring phyllodulcin (1) was orally administered to rats to investigate its metabolic fate. Urinary metabolites were analyzed by three-dimensional HPLC. Phyllodulcin-3'-0-sulfate (2), phyllodulcin-3'-0- -glucuronide (3),2-[2-(3,4-dihydroxyphenyl)ethyl]-6-hydroxybenzoic acid (4), and one novel bibenzyl derivative, 2-[2-(3-hydroxy-4-methoxyphenyl)ethyl]-6-hydroxybenzoic acid (5), together with thunberginol G (6) and hydrangenol (7) were isolated from the phyllodulcin-treated urine. 1 was extensively metabolized to 4-6 by a rat fecal suspension after incubation for 24 h. Urinary excretion of 4-6 in rats administered phyllodulcin orally was substantially reduced when the rats were treated with antibiotics to suppress their intestinal flora. On the other hand, the incubation of 1 with rat liver S-9 mix showed the presence of 7 together with 4 and 5.

  DOI：

  10.1021/np0400353

文献信息

• Asahina; Asano, Chemische Berichte, 1929, vol. 62, p. 172,176
  作者：Asahina、Asano

  DOI：——

  日期：——
• Metabolic Fate of Orally Administered Phyllodulcin in Rats
  作者：Takaaki Yasuda、Saiko Kayaba、Kana Takahashi、Takahiro Nakazawa、Keisuke Ohsawa

  DOI：10.1021/np0400353

  日期：2004.9.1

  Naturally occurring phyllodulcin (1) was orally administered to rats to investigate its metabolic fate. Urinary metabolites were analyzed by three-dimensional HPLC. Phyllodulcin-3'-0-sulfate (2), phyllodulcin-3'-0- -glucuronide (3),2-[2-(3,4-dihydroxyphenyl)ethyl]-6-hydroxybenzoic acid (4), and one novel bibenzyl derivative, 2-[2-(3-hydroxy-4-methoxyphenyl)ethyl]-6-hydroxybenzoic acid (5), together with thunberginol G (6) and hydrangenol (7) were isolated from the phyllodulcin-treated urine. 1 was extensively metabolized to 4-6 by a rat fecal suspension after incubation for 24 h. Urinary excretion of 4-6 in rats administered phyllodulcin orally was substantially reduced when the rats were treated with antibiotics to suppress their intestinal flora. On the other hand, the incubation of 1 with rat liver S-9 mix showed the presence of 7 together with 4 and 5.