(3R,4R)-3,4-bis(3-hydroxybenzyl)-tetrahydrofuran-2-ol | 1176223-72-5

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 呋喃类木脂素
• 英文名称: (3R,4R)-3,4-bis(3-hydroxybenzyl)-tetrahydrofuran-2-ol
• 英文别名: enterolactol
• CAS: 1176223-72-5
• 化学式: C₁₈H₂₀O₄
• 分子量: 300.354
• InChiKey: UQDJKRBMWCHPCE-ZGRMHCKUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.46
• 重原子数：
  22.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  69.92
• 氢给体数：
  3.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  (-)-enterolactone 在 三乙基硼氢化锂 作用下， 生成 (3R,4R)-3,4-bis(3-hydroxybenzyl)-tetrahydrofuran-2-ol
  参考文献：
  名称：

  Further Studies on a Human Intestinal Bacterium Ruminococcus sp. END-1 for Transformation of Plant Lignans to Mammalian Lignans

  摘要：

  A human intestinal bacterium Ruminococcus (R.) sp. END-1 capable of oxidizing (-)-enterodiol to (-)-enterolactone, enantioselectively, was further investigated from the perspective of transformation of plant lignans to mammalian lignans; A cell-free extract of the bacterium transformed (-)-enterodiol to (-)-enterolactone through an intermediate, enterolactol. The bacterium showed not only oxidation but also demethylation and deglucosylation activities for plant lignans. Arctiin and secoisolariciresinol diglucoside were converted to (-)-dihydroxyenterolactone and (+)-dihydroxyenterodiol, respectively. Moreover, by coincubation with Eggerthella sp. SDG-2, the bacterium transformed arctiin and secoisolariciresinol diglucoside to (-)-enterolactone and (+)-enterodiol, respectively.

  DOI：

  10.1021/jf900902p