(2S)-7-hydroxy-8-hydroxyethyl-4'-methoxyflavane-2'-O-β-D-glucopyranoside | 1304653-67-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: (2S)-7-hydroxy-8-hydroxyethyl-4'-methoxyflavane-2'-O-β-D-glucopyranoside
• 英文别名: 7,2'-dihydroxy-8-hydroxyethyl-4'-methoxyflavane-2'-O-β-D-glucopyranoside；(2S,3R,4S,5S,6R)-2-[2-[(2S)-7-hydroxy-8-(2-hydroxyethyl)-3,4-dihydro-2H-chromen-2-yl]-5-methoxyphenoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 1304653-67-5
• 化学式: C₂₄H₃₀O₁₀
• 分子量: 478.496
• InChiKey: IEZGCKDRCQFGIH-QCZHZLPESA-N

物化性质

• 沸点：
  755.7±60.0 °C(Predicted)
• 密度：
  1.444±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  34
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  158
• 氢给体数：
  6
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  (2S)-7-hydroxy-8-hydroxyethyl-4'-methoxyflavane-2'-O-β-D-glucopyranoside 在 盐酸 、 水 作用下， 以 乙酸乙酯 为溶剂， 反应 2.0h， 生成 可得然胶
  参考文献：
  名称：

  Flavonoids from silkworm droppings and their promotional activities on heme oxygenase-1

  摘要：

  A new flavane glucoside, 7,2'-dihydroxy-8-hydroxyethyl-4'-methoxyflavane-2'-O--d-glucopyranoside (3), along with three known flavonoids, 7,2'-dihydroxy-8-prenyl-4'-methoxyflavane (1), euchrenone a7 (2), and 7,2'-dihydroxy-8-prenyl-4'-methoxy-2'-O--d-glucopyranosylflavane (4), was isolated from silkworm droppings. The structures of the compounds were elucidated on the basis of 1D and 2D NMR spectroscopic analyses and optical rotational characteristics. The compounds isolated from silkworm droppings were evaluated for their effects on heme oxygenase-1 (HO-1) activity. Compounds 1 and 3 increased the expression of HO-1 in HepG2 cells. HO-1 is an antioxidant enzyme that catabolizes heme to carbon monoxide, free iron, and biliverdin, all of which are involved in the suppression of inflammatory mediators.

  DOI：

  10.1080/10286020.2011.555331

文献信息

• Flavonoids from silkworm droppings and their promotional activities on heme oxygenase-1
  作者：Ji-Hae Park、Dae-Young Lee、Pyeong Yun、Seung-Woo Yeon、Jong Hee Ko、Yong-Soon Kim、Nam-In Baek

  DOI：10.1080/10286020.2011.555331

  日期：2011.4

  A new flavane glucoside, 7,2'-dihydroxy-8-hydroxyethyl-4'-methoxyflavane-2'-O--d-glucopyranoside (3), along with three known flavonoids, 7,2'-dihydroxy-8-prenyl-4'-methoxyflavane (1), euchrenone a7 (2), and 7,2'-dihydroxy-8-prenyl-4'-methoxy-2'-O--d-glucopyranosylflavane (4), was isolated from silkworm droppings. The structures of the compounds were elucidated on the basis of 1D and 2D NMR spectroscopic analyses and optical rotational characteristics. The compounds isolated from silkworm droppings were evaluated for their effects on heme oxygenase-1 (HO-1) activity. Compounds 1 and 3 increased the expression of HO-1 in HepG2 cells. HO-1 is an antioxidant enzyme that catabolizes heme to carbon monoxide, free iron, and biliverdin, all of which are involved in the suppression of inflammatory mediators.