α,β-epoxy-3,2',4',6'-tetrakis(benzyloxy)-4-methoxychalcone | 76260-66-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: α,β-epoxy-3,2',4',6'-tetrakis(benzyloxy)-4-methoxychalcone
• 英文别名: [3-(4-Methoxy-3-phenylmethoxyphenyl)oxiran-2-yl]-[2,4,6-tris(phenylmethoxy)phenyl]methanone
• CAS: 76260-66-7
• 化学式: C₄₄H₃₈O₇
• 分子量: 678.782
• InChiKey: BFCUTAUNFVITPV-UHFFFAOYSA-N

物化性质

• 沸点：
  834.2±65.0 °C(Predicted)
• 密度：
  1.237±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.7
• 重原子数：
  51
• 可旋转键数：
  16
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  75.8
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  α,β-epoxy-3,2',4',6'-tetrakis(benzyloxy)-4-methoxychalcone 在 palladium on activated charcoal 盐酸 、 氢气 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以88%的产率得到3,5,7,3'-tetrahydroxy-4'-methoxyflavanone
  参考文献：
  名称：

  Potential sweetening agents of plant origin. 13. An intensely sweet dihydroflavonol derivative based on a natural product lead compound

  摘要：

  The dihydroflavonol dihydroquercetin 3-acetate (1) was isolated as a sweet constituent of the young shoots of Tessaria dodoneifolia (Hook. & Arn.) Cabrera (Compositae). Compound 1 and dihydroquercetin 3-acetate 4'-(methyl ether) (2), a novel synthetic analogue of this natural product lead compound, were rated by a taste panel as being 80 and 400 times sweeter than a 2% w/v sucrose solution, respectively. Synthetic dihydroquercetin 4'-(methyl ether) (3) showed a reduced sweetness intensity when compared to 2, while (+)-dihydroquercetin (4) was devoid of sweetness. Dihydroflavonol derivatives 1-3 represent a new class of potentially noncaloric and noncariogenic intense sweeteners.

  DOI：

  10.1021/jm00401a030
• 作为产物：
  描述：

  (S)-2,3-dihydro-5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-4-benzopyrone 在 sodium hydroxide 、 双氧水 、 potassium carbonate 作用下， 以 甲醇 、 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 23.0h， 生成 α,β-epoxy-3,2',4',6'-tetrakis(benzyloxy)-4-methoxychalcone
  参考文献：
  名称：

  Potential sweetening agents of plant origin. 13. An intensely sweet dihydroflavonol derivative based on a natural product lead compound

  摘要：

  The dihydroflavonol dihydroquercetin 3-acetate (1) was isolated as a sweet constituent of the young shoots of Tessaria dodoneifolia (Hook. & Arn.) Cabrera (Compositae). Compound 1 and dihydroquercetin 3-acetate 4'-(methyl ether) (2), a novel synthetic analogue of this natural product lead compound, were rated by a taste panel as being 80 and 400 times sweeter than a 2% w/v sucrose solution, respectively. Synthetic dihydroquercetin 4'-(methyl ether) (3) showed a reduced sweetness intensity when compared to 2, while (+)-dihydroquercetin (4) was devoid of sweetness. Dihydroflavonol derivatives 1-3 represent a new class of potentially noncaloric and noncariogenic intense sweeteners.

  DOI：

  10.1021/jm00401a030

文献信息

• [EN] DIHYDROFLAVONOL DERIVATIVES USEFUL AS SWEETENERS
  申请人：UNIVERSITY PATENTS, INC.

  公开号：WO1988008256A1

  公开（公告）日：1988-11-03

  (EN) Certain dihydroflavonol derivatives are disclosed as being intensely sweet.(FR) Certains dérivés de dihydroflavonol sont des édulcorants très forts.
• Potential sweetening agents of plant origin. 13. An intensely sweet dihydroflavonol derivative based on a natural product lead compound
  作者：N. P. Dhammika Nanayakkara、Raouf A. Hussain、John M. Pezzuto、D. Doel Soejarto、A. Douglas Kinghorn

  DOI：10.1021/jm00401a030

  日期：1988.6

  The dihydroflavonol dihydroquercetin 3-acetate (1) was isolated as a sweet constituent of the young shoots of Tessaria dodoneifolia (Hook. & Arn.) Cabrera (Compositae). Compound 1 and dihydroquercetin 3-acetate 4'-(methyl ether) (2), a novel synthetic analogue of this natural product lead compound, were rated by a taste panel as being 80 and 400 times sweeter than a 2% w/v sucrose solution, respectively. Synthetic dihydroquercetin 4'-(methyl ether) (3) showed a reduced sweetness intensity when compared to 2, while (+)-dihydroquercetin (4) was devoid of sweetness. Dihydroflavonol derivatives 1-3 represent a new class of potentially noncaloric and noncariogenic intense sweeteners.