2H-1-苯并吡喃-3,7,8-三醇,2-(3,4-二羟基苯基)-3,4-二氢-,(2R,3S)- | 109671-55-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 中文名称: 2H-1-苯并吡喃-3,7,8-三醇,2-(3,4-二羟基苯基)-3,4-二氢-,(2R,3S)-
• 英文名称: 2,3-trans-3',4',7,8-tetrahydroxyflavan-3-ol
• 英文别名: (+)-Mesquitol；mesquitol；(-)-mesoquitol；(2R,3S)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-chromene-3,7,8-triol
• CAS: 109671-55-8
• 化学式: C₁₅H₁₄O₆
• 分子量: 290.273
• InChiKey: TXULLYMENMRLHL-GXTWGEPZSA-N

物化性质

• 沸点：
  604.4±55.0 °C(Predicted)
• 密度：
  1.593±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  110
• 氢给体数：
  5
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2H-1-苯并吡喃-3,7,8-三醇,2-(3,4-二羟基苯基)-3,4-二氢-,(2R,3S)- 在 吡啶 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 48.0h， 生成 (2R,3S)-2,3-trans-3-acetoxy-3',4',7,8-tetramethoxyflavan
  参考文献：
  名称：

  Young, Esme; Brandt, Edward V.; Young, Desmond A., Journal of the Chemical Society. Perkin transactions I, 1986, p. 1737 - 1750

  摘要：

  DOI：

文献信息

• An unusual reaction of flavan-3-ols with acetone of relevance to the formation of the tetracyclic ring system in peltogynoids
  作者：Jan H. Van Der westhuizen、Jacobus A. Steenkamp、Daneel Ferreira

  DOI：10.1016/s0040-4020(01)90082-1

  日期：1990.1

  Flavan-3-ols are in moist acetone subject to acid-catalyzed incorporation of an 1-methylethylidene fragment between 3-OH and C-2 (B-ring) to give a tetracyclic ring system reminiscent of the peltogynoid series of flavonoids.

  黄烷-3-醇在潮湿的丙酮中，经过酸催化的3-OH和C-2之间的1-甲基亚乙基片段的掺入（B环），产生了一个四环系统，让人联想到类雌激素的类黄酮。
• Tyrosinase catalysed biphenyl construction from flavan-3-ol substrates
  作者：Werner Janse van Rensburg、Daneel Ferreira、Elfranco Malan、Jacobus A. Steenkamp

  DOI：10.1016/s0031-9422(99)00476-8

  日期：2000.1

  Mushroom tyrosinase catalysed oxidation of three flavan-3-ols, viz. catechin, fisetinidol and mesquitol, was conducted to construct biphenyl bonds. Exposure of the flavan-3-ols to tyrosinase and subsequent trapping of the o-quinone intermediates resulted in the formation of novel flavan-3-ol derivatives, the structures of which were elucidated by mono- and two-dimensional 1H-NMR experiments. Application of the methodology resulted in the improved synthesis of the natural flavan-3-ol dimer, mesquitol-[5-->8]-catechin, previously isolated from Prosopis glandulosa.
• Unusual amount of (−)-mesquitol from the heartwood of <i>Prosopis juliflora</i>
  作者：Peter Sirmah、Stéphane Dumarçay、Eric Masson、Philippe Gérardin

  DOI：10.1080/14786410801940968

  日期：2009.1.20

  A large amount of flavonoid has been extracted and isolated from the heartwood of Prosopis juliflora, an exogenous wood species of Kenya. Structural and physicochemical elucidation based on FTIR, 1H and 13C NMR, GC-MS and HPLC analysis clearly demonstrated the presence of (-)-mesquitol as the sole compound without any noticeable impurities. The product was able to slow down oxidation of methyl linoleate induced by AIBN. The important amount and high purity of (-)-mesquitol present in the acetonic extract of P. juliflora could therefore be of valuable interest as a potential source of antioxidants from a renewable origin.
• Brandt, E. Vincent; Young, Desmond A.; Young, Esme, Journal of the Chemical Society. Perkin transactions II, 1987, p. 1365 - 1368
  作者：Brandt, E. Vincent、Young, Desmond A.、Young, Esme、Ferreira, Daneel

  DOI：——

  日期：——
• Young, Desmond A.; Young, Esme; Roux, David G., Journal of the Chemical Society. Perkin transactions I, 1987, p. 2345 - 2352
  作者：Young, Desmond A.、Young, Esme、Roux, David G.、Brandt, E. Vincent、Ferreira, Daneel

  DOI：——

  日期：——