3,5,7,3'-tetrahydroxy-4'-methoxyflavanone | 70411-27-7

• 物质功能分类: 天然产物 - 黄酮类化合物
• 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: 3,5,7,3'-tetrahydroxy-4'-methoxyflavanone
• 英文别名: dihydroquercetin 4'-(methyl ether)；dihydroquercetin-4'-methyl ether；dihydrotamarixetin；3,5,7-trihydroxy-2-(3-hydroxy-4-methoxy-phenyl)-chroman-4-one；3,5,7-Trihydroxy-2-(3-hydroxy-4-methoxy-phenyl)-chroman-4-on；3,5,7-Trihydroxy-2-(3-hydroxy-4-methoxyphenyl)-2,3-dihydrochromen-4-one
• CAS: 70411-27-7；82517-11-1；114179-12-3
• 化学式: C₁₆H₁₄O₇
• 分子量: 318.283
• InChiKey: KQNGHARGJDXHKF-UHFFFAOYSA-N

物化性质

• 熔点：
  172-174 °C
• 沸点：
  642.9±55.0 °C(Predicted)
• 密度：
  1.558±0.06 g/cm3(Predicted)
• 物理描述：
  Solid

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  116
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3,5,7,3'-tetrahydroxy-4'-methoxyflavanone 在 potassium pyrosulfite 作用下， 以 乙醇 为溶剂， 以50%的产率得到柽柳黄素
  参考文献：
  名称：

  Synthesis and antioxygenic activities of seabuckthorn flavone-3-ols and analogs

  摘要：

  A practical synthesis of polyhydroxy- and regiospecifically methylated flavone-3-ols which are components of commercial 'seabuckthorn flavone' has been achieved by modified Algar-Flynn-Oyamada method. Antioxidant activities of seabuckthorn extracts, isolated products and a number of flavone-3-ols have been determined. Structure-activity relationships have been discussed. Amongst the compounds tested, gallic acid, which is also present in seabuckthorn, was found to be the most effective antioxidant and radioprotectant. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.07.008
• 作为产物：
  描述：

  (S)-2,3-dihydro-5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-4-benzopyrone 在 palladium on activated charcoal 盐酸 、 sodium hydroxide 、 氢气 、 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 27.0h， 生成 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

文献信息

• Goel; Seshadri, Proceedings - Indian Academy of Sciences, Section A, 1958, # 47, p. 191,193
  作者：Goel、Seshadri

  DOI：——

  日期：——
• NANAYAKKARA, N. P. DHAMMIKA;HUSSAIN, RAOUF A.;PEZZUTO, JOHN M.;SOEJARTO, +, J. MED. CHEM., 31,(1988) N 6, 1250-1253
  作者：NANAYAKKARA, N. P. DHAMMIKA、HUSSAIN, RAOUF A.、PEZZUTO, JOHN M.、SOEJARTO, +

  DOI：——

  日期：——
• CONJUGATES OF HUPERZINE AND ANALOGS THEREOF
  申请人：INSERO HEALTH INC.

  公开号：US20150191430A1

  公开（公告）日：2015-07-09

  Compounds and compositions for treating neurodegenerative diseases are described. The compounds include a therapeutic agent covalently linked with huperzine or an analog thereof through a linker. Methods of preparing the compounds are described. Methods of treating a neurodegenerative disease by administering compounds and compositions including a therapeutic agent covalently linked with huperzine or an analog thereof are described. Methods for delivering a therapeutic agent by administering the therapeutic agent covalently linked to huperzine or an analog thereof are described.
• Synthesis and antioxygenic activities of seabuckthorn flavone-3-ols and analogs
  作者：N. Pandurangan、Chinchu Bose、A. Banerji

  DOI：10.1016/j.bmcl.2011.07.008

  日期：2011.9

  A practical synthesis of polyhydroxy- and regiospecifically methylated flavone-3-ols which are components of commercial 'seabuckthorn flavone' has been achieved by modified Algar-Flynn-Oyamada method. Antioxidant activities of seabuckthorn extracts, isolated products and a number of flavone-3-ols have been determined. Structure-activity relationships have been discussed. Amongst the compounds tested, gallic acid, which is also present in seabuckthorn, was found to be the most effective antioxidant and radioprotectant. (C) 2011 Elsevier Ltd. All rights reserved.
• 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.