2,3',6-trihydroxy-4-(carboxymethoxy)-4'-methoxydihydrochalcone | 61497-77-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 2,3',6-trihydroxy-4-(carboxymethoxy)-4'-methoxydihydrochalcone
• 英文别名: 4-O-Carboxymethyl-hesperetin-dihydrochalcon；2-[3,5-Dihydroxy-4-[3-(3-hydroxy-4-methoxyphenyl)propanoyl]phenoxy]acetic acid
• CAS: 61497-77-6
• 化学式: C₁₈H₁₈O₈
• 分子量: 362.336
• InChiKey: HHVUOGRDZDYFTL-UHFFFAOYSA-N

物化性质

• 沸点：
  663.3±55.0 °C(Predicted)
• 密度：
  1.434±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  134
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2,3',6-trihydroxy-4-(carboxymethoxy)-4'-methoxydihydrochalcone 在 sodium hydroxide 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.33h， 生成 6-(2-{3,5-Dihydroxy-4-[3-(3-hydroxy-4-methoxy-phenyl)-propionyl]-phenoxy}-acetylamino)-hexanoic acid
  参考文献：
  名称：

  与ω-氨基酸或其低聚物相关的橙皮素二氢查尔酮衍生物的甜度

  摘要：

  合成并品尝了具有ω-氨基酸、低聚甘氨酸或低聚-(γ-氨基丁酸)的橙皮素二氢查耳酮衍生物。引入基团的疏水性对于理解这些化合物的结构-甜味关系很重要，但还必须考虑除疏水性之外的其他因素。

  DOI：

  10.1246/bcsj.56.347
• 作为产物：
  描述：

  3-<2-(3-hydroxy-4-methoxyphenyl)ethyl>-4-hydroxy-6-(carboxymethoxy)-1,2benzisoxazole 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 、 水 为溶剂， 反应 0.5h， 生成 2,3',6-trihydroxy-4-(carboxymethoxy)-4'-methoxydihydrochalcone 、 1-<2,6-dihydroxy-4-(carboxymethoxy)phenyl>-3-<3-hydroxy-4-methoxyphenyl>propan-1-imine
  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

文献信息

• Sweetness of Hesperetin Dihydrochalcone Derivatives Linked to ω-Amino Acid or Its Oligomer
  作者：Masao Kawai、Kyoko Kuwabara、Ritsuko Kimura、Sachiko Sekido

  DOI：10.1246/bcsj.56.347

  日期：1983.1

  Derivatives of hesperetin dihydrochalcone having ω-amino acid, oligoglycine, or oligo-(γ-aminobutyric acid) were synthesized and tasted. The hydrophobicity of the introduced group is important for understanding the structure-sweet taste relationship of these compounds, though other factors than hydrophobicity also must be taken into account.

  合成并品尝了具有ω-氨基酸、低聚甘氨酸或低聚-(γ-氨基丁酸)的橙皮素二氢查耳酮衍生物。引入基团的疏水性对于理解这些化合物的结构-甜味关系很重要，但还必须考虑除疏水性之外的其他因素。
• Dihydrochalcone sweeteners. A study of the atypical temporal phenomena
  作者：Grant E. DuBois、Guy A. Crosby、Rebecca A. Stephenson

  DOI：10.1021/jm00136a011

  日期：1981.4

  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.