4'-rhamnoglucosyloxy-2',4,6'-trihydroxychalcone | 50376-43-7

• 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: 4'-rhamnoglucosyloxy-2',4,6'-trihydroxychalcone
• 英文别名: 4'-rhamnoglucosyl-2',6',4-trihydroxychalcone；naringin chalcone；4,2',6'-trihydroxy-4'-(O²-α-L-rhamnopyranosyl-β-D-glucopyranosyloxy)-trans--chalcone；4,2',6'-Trihydroxy-4'-(O²-α-L-rhamnopyranosyl-β-D-glucopyranosyloxy)-trans--chalkon；(E)-1-[4-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-2,6-dihydroxyphenyl]-3-(4-hydroxyphenyl)prop-2-en-1-one
• CAS: 50376-43-7
• 化学式: C₂₇H₃₂O₁₄
• 分子量: 580.543
• InChiKey: IXVXIWLKOMVSFY-GOZPEMRWSA-N

物化性质

• 熔点：
  201-202 °C
• 沸点：
  932.7±65.0 °C(Predicted)
• 密度：
  1.65±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  41
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  236
• 氢给体数：
  9
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  4'-rhamnoglucosyloxy-2',4,6'-trihydroxychalcone 在 盐酸 、 palladium on activated charcoal 、 乙醇 作用下， 生成 根皮素
  参考文献：
  名称：

  Jorio, Annali di Chimica, 1959, vol. 49, p. 1929,1936

  摘要：

  DOI：
• 作为产物：
  描述：

  naringin 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 生成 4'-rhamnoglucosyloxy-2',4,6'-trihydroxychalcone
  参考文献：
  名称：

  Gonzalez, Evangelina A.; Nazareno, Monica A.; Borsarelli, Claudio D., Journal of the Chemical Society. Perkin Transactions 2 (2001), 2002, # 12, p. 2052 - 2056

  摘要：

  DOI：

文献信息

• The kinetics and mechanism, and the equilibrium position as a function of pH, of the isomerisation of naringin and the 4′-rhamnoglucoside of 2′,4,4′,6′-tetrahydroxychalcone
  作者：Christopher O. Miles、Lyndsay Main

  DOI：10.1039/p29880000195

  日期：——

  quantitatively accommodated for the first time. The rate data have been used to calculate the position of the equilibrium and its rate of attainment as a function of pH, and this information should be of general value for optimising conditions for synthesis of 2′,4,6′-trihydroxychalcones by ring-opening 4′,5-dihydroxyflavanones.

  已经确定了标题反应的pH值速率分布，并根据各种离子化物种的贡献进行了解释。查耳酮4-OH基团的电离对环化速率的影响是第一次定量地获得。速率数据已用于计算平衡的位置及其达到pH的函数，该信息对于优化环式合成2'，4,6'-三羟基查耳酮的条件应具有一般价值。开口4'，5-二羟基黄酮。
• Interconversion of Chalcones and Flavanones of a Phloroglucinol-type Structure
  作者：Masami Shimokoriyama

  DOI：10.1021/ja01572a057

  日期：1957.8
• METHOD FOR THE BIOTECHNOLOGICAL PRODUCTION OF FLAVONE GLYCOSIDE DIHYDROCHALCONES
  申请人：Symrise AG

  公开号：US20180216152A1

  公开（公告）日：2018-08-02

  The invention relates to a method for producing flavone glycoside dihydrochalcones, having the following steps: (a) providing a transgenic microorganism containing (i) a first nucleic acid portion (A) containing a gene which codes for a bacterial chalcone isomerase and (ii) a second nucleic acid portion (B) containing a gene which codes for a bacterial enoate reductase, (b) adding one or more flavone glycosides to the transgenic microorganism under conditions which allow the simultaneous isomerization and reduction of the flavone glycoside into the flavone glycoside dihydrochalcone, and optionally (d) isolating and purifying the final product, wherein the nucleic acid portion (A) (1) is a nucleotide sequence according to SEQ ID NO:1, in which the nucleic acid portion (A′) according to SEQ ID NO:3 has been cut out, or (2) is an amino acid sequence according to SEQ ID NO:2, in which the amino acid portion (A′) according to SEQ ID NO:4 has been cut out.
• Jorio, Annali di Chimica, 1959, vol. 49, p. 1929,1936
  作者：Jorio

  DOI：——

  日期：——
• Gonzalez, Evangelina A.; Nazareno, Monica A.; Borsarelli, Claudio D., Journal of the Chemical Society. Perkin Transactions 2 (2001), 2002, # 12, p. 2052 - 2056
  作者：Gonzalez, Evangelina A.、Nazareno, Monica A.、Borsarelli, Claudio D.

  DOI：——

  日期：——