benzyl 1α,3β,4β-trihydroxy-5α-<<3-(3-hydroxy-4-methoxyphenyl)propenoyl>oxy>cyclohexane-β-carboxylate | 76799-19-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzyl 1α,3β,4β-trihydroxy-5α-<<3-(3-hydroxy-4-methoxyphenyl)propenoyl>oxy>cyclohexane-β-carboxylate
• 英文别名: benzyl 1α,3β,4β-trihydroxy-5α-{[3-(3-hydroxy-4-methoxyphenyl)propenoyl]oxy}cyclohexane-β-carboxylate
• CAS: 76799-19-4
• 化学式: C₂₄H₂₆O₉
• 分子量: 458.465
• InChiKey: AKVJQESEEURMTF-HLEPYXMKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.32
• 重原子数：
  33.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  142.75
• 氢给体数：
  4.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  benzyl 1α,3β,4β-trihydroxy-5α-<<3-(3-hydroxy-4-methoxyphenyl)propenoyl>oxy>cyclohexane-β-carboxylate 在 palladium on activated charcoal 氢气 作用下， 以 四氢呋喃 为溶剂， 反应 96.0h， 以38%的产率得到1α,3β,4β-trihydroxy-5α-{[3-(3-hydroxy-4-methoxyphenyl)propanoyl]oxy}cyclohexane-β-carboxylic acid
  参考文献：
  名称：

  Dihydrochalcone sweeteners. A study of the atypical temporal phenomena

  摘要：

  Neohesperidin dihydrochalcone (NHDHC), known since 1963 as an intensely sweet compound, is determined to be 340 +/- 60 (p less than 0.05) times more potent than sucrose. The unusual temporal properties of this material are hypothesized as being due to the effects of metabolism, conformation, chelation, or hydrophobicity. Forty-four analogues are synthesized to test the four hypotheses, none of which are strongly supported. A method of quantitation of temporal characteristics of tastant molecules is developed so as to allow comparison of taste appearance time (AT) and extinction time (ET) of experimental compounds. Four of the new compounds, 40 and 43-45, exhibit high sweetness potencies, ranging from 280 and 440 times sucrose, and may be useful in selected food systems. The temporal taste characteristics remain unimproved over NHDHC, however.

  DOI：

  10.1021/jm00136a011
• 作为产物：
  描述：

  (-)-5-咖啡酰奎宁酸 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 162.0h， 生成 benzyl 1α,3β,4β-trihydroxy-5α-<<3-(3-hydroxy-4-methoxyphenyl)propenoyl>oxy>cyclohexane-β-carboxylate
  参考文献：
  名称：

  Dihydrochalcone sweeteners. A study of the atypical temporal phenomena

  摘要：

  Neohesperidin dihydrochalcone (NHDHC), known since 1963 as an intensely sweet compound, is determined to be 340 +/- 60 (p less than 0.05) times more potent than sucrose. The unusual temporal properties of this material are hypothesized as being due to the effects of metabolism, conformation, chelation, or hydrophobicity. Forty-four analogues are synthesized to test the four hypotheses, none of which are strongly supported. A method of quantitation of temporal characteristics of tastant molecules is developed so as to allow comparison of taste appearance time (AT) and extinction time (ET) of experimental compounds. Four of the new compounds, 40 and 43-45, exhibit high sweetness potencies, ranging from 280 and 440 times sucrose, and may be useful in selected food systems. The temporal taste characteristics remain unimproved over NHDHC, however.

  DOI：

  10.1021/jm00136a011