1,2-双(4-羟基-3-甲氧基苯基)乙酮 | 5438-67-5

• 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: 1,2-双(4-羟基-3-甲氧基苯基)乙酮
• 英文名称: 1,2-bis(4-hydroxy-3-methoxyphenyl)-1-ethanone
• 英文别名: 1,2-bis(4-hydroxy-3-methoxyphenyl)ethanone；melicopone；4,4'-dihydroxy-3,3'-dimethoxy-deoxybenzoin；4,4'-Dihydroxy-3,3'-dimethoxy-desoxybenzoin
• CAS: 5438-67-5
• 化学式: C₁₆H₁₆O₅
• 分子量: 288.3
• InChiKey: URFHJEVBFJOWKL-UHFFFAOYSA-N

物化性质

• 熔点：
  154–155°C
• 沸点：
  506.0±45.0 °C(Predicted)
• 密度：
  1.272±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 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：
  76
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1,2-双(4-羟基-3-甲氧基苯基)乙酮 在 sodium hydroxide 、 镍 作用下， 生成 4-[(E)-2-(4-羟基-3-甲氧基苯基)乙烯基]-2-甲氧基苯酚
  参考文献：
  名称：

  Reactions of Vanillin and its Derived Compounds. XX.¹ The Reduction of Vanillil²

  摘要：

  DOI：

  10.1021/ja01138a043
• 作为产物：
  描述：

  1,2-双(4-羟基-3-甲氧基苯基)乙烷-1,2-二酮 在 乙醇 、 氯化铵 、 锌 作用下， 生成 1,2-双(4-羟基-3-甲氧基苯基)乙酮
  参考文献：
  名称：

  Reactions of Vanillin and its Derived Compounds. XX.¹ The Reduction of Vanillil²

  摘要：

  DOI：

  10.1021/ja01138a043

文献信息

• Identification of Enterodiol as a Masker for Caffeine Bitterness by Using a Pharmacophore Model Based on Structural Analogues of Homoeriodictyol
  作者：Jakob P. Ley、Marco Dessoy、Susanne Paetz、Maria Blings、Petra Hoffmann-Lücke、Katharina V. Reichelt、Gerhard E. Krammer、Silke Pienkny、Wolfgang Brandt、Ludger Wessjohann

  DOI：10.1021/jf301335z

  日期：2012.6.27

  Starting from previous structure-activity relationship studies of taste modifiers based on homoeriodictyol, dihydrochalcones, deoxybenzoins, and trans-3-hydroxyflavones as obvious analogues were investigated for their masking effect against caffeine. The most active compounds of the newly investigated taste modifiers were phloretin, the related dihydrochalcones 3-methoxy-2',4,4'-trihydroxydihydrochalcone and 2',4-dihydroxy-3-methoxydihydrochalcone, and the deoxybenzoin 2-(4-hydroxy-3-methoxyphenyl)-1-(4-hydroxyphenyl)ethanone. Starting with the whole set of compounds showing activity >22%, a (Q)SAR pharmacophore model for maskers of caffeine bitterness was calculated to explain the structural requirements. After docking of the pharmacophore into a structural model of the broadly tuned bitter receptor hTAS2R10 and docking of enterolactone and enterodiol as only very weakly related structures, it was possible to predict qualitatively their modulating activity. Enterodiol (25 mg L-1) reduced the bitterness of the 500 mg L-1 caffeine solution by about 30%, whereas enterolactone showed no masking but a slight bitter-enhancing effect.
• The early oxidative biodegradation steps of residual kraft lignin models with laccase
  作者：Claudia Crestini、Dimitris S. Argyropoulos

  DOI：10.1016/s0968-0896(98)00173-4

  日期：1998.11

  A number of model compounds resembling the fundamental bonding patterns of residual kraft lignin, including a series of stilbenes, were incubated with laccase from Trametes versicolor in the presence and absence of delignification 'mediators' ABTS and HBT. The condensed kraft lignin model compounds seem to undergo initial degradation by laccase mainly via benzylic oxidation, demethylation and hydroxylation reactions. Phenolic 5-5', diphenylmethane and alpha-5 lignin models were found to be degraded mainly via side-chain oxidation reactions. Among the models studied, a phenolic stilbene was found to be the most reactive, yielding several products showing side-chain oxidation/transposition, demethoxylation and hydroxylation reactions. Non-phenolic 5-5', diphenylmethane and stilbene model compounds were found unreactive even in the presence of the laccase-mediator system. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Berndtsson, Ingmar; Khanna, Bhushan L.; Lundquist, Knut, Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1980, vol. 34, # 6, p. 453 - 455
  作者：Berndtsson, Ingmar、Khanna, Bhushan L.、Lundquist, Knut

  DOI：——

  日期：——
• Studies on Lignin and Related Products. IX.¹ Cupric Oxide Oxidation of Lignin Model Substances^2,3
  作者：Irwin A. Pearl、Donald L. Beyer

  DOI：10.1021/ja01637a060

  日期：1954.4