(2R,3R,4S)-4-(2,4,6-trihydroxyphenyl)flavan-3,3',4',5,7-pentaol | 61541-06-8

• 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: (2R,3R,4S)-4-(2,4,6-trihydroxyphenyl)flavan-3,3',4',5,7-pentaol
• 英文别名: (-)-epicatechin-(4β->2)-phloroglucinol；epicatechin-(4β->2)-phloroglucinol；epicatechin-(4β→2)-phloroglucinol；epicatechin-(4β-2)-phloroglucinol；(-)-epicatechin-4-phloroglucinol；4-(2-phloroglucinol)-(-)-epicatechin；Prodelphinidin B6；(2R,3R,4S)-2-(3,4-dihydroxyphenyl)-4-(2,4,6-trihydroxyphenyl)-3,4-dihydro-2H-chromene-3,5,7-triol
• CAS: 61541-06-8；78284-51-2；79199-52-3；79199-53-4；104320-35-6；141605-03-0；61541-02-4
• 化学式: C₂₁H₁₈O₉
• 分子量: 414.369
• InChiKey: OKJJBTUOKCQSPH-PWRODBHTSA-N

物化性质

• 熔点：
  225-230 °C
• 沸点：
  723.3±60.0 °C(Predicted)
• 密度：
  1.714±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  30
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  171
• 氢给体数：
  8
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (2R,3R,4S)-4-(2,4,6-trihydroxyphenyl)flavan-3,3',4',5,7-pentaol 在 盐酸 、 ammonium ferric sulfate 作用下， 以 甲醇 、 正丁醇 为溶剂， 反应 0.67h， 生成 花色素
  参考文献：
  名称：

  The conversion of procyanidins and prodelphinidins to cyanidin and delphinidin

  摘要：

  DOI：

  10.1016/s0031-9422(00)94533-3
• 作为产物：
  描述：

  2-((2R,3R,4S)-5,7-bis(benzyloxy)-2-(3,4-bis(benzyloxy)phenyl)-3-hydroxychroman-4-yl)benzene-1,3,5-triol 在 20% palladium hydroxide on carbon 、 氢气 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 20.0 ℃ 、200.0 kPa 条件下， 反应 4.0h， 以86%的产率得到(2R,3R,4S)-4-(2,4,6-trihydroxyphenyl)flavan-3,3',4',5,7-pentaol
  参考文献：
  名称：

  Synthesis and ribonuclease A inhibition activity of resorcinol and phloroglucinol derivatives of catechin and epicatechin: Importance of hydroxyl groups

  摘要：

  The reported ribonuclease A inhibitory activity of the green tea extracts prompted us to synthesize novel catechin/epicatechin based conjugates with resorcinol and phloroglucinol with the aim to increase the number of phenolic OH groups. These are found to be more effective inhibitors of ribonuclease A as compared to catechin and epicatechin thus indicating the importance of number of phenolic OH groups for the inhibition of ribonucleolytic activity. Fluorescence studies have been carried out to evaluate the binding parameters. The protein-ligand docking studies are also performed to gain insight into the protein-polyphenols interactions. The epicatechin based polyphenols 1 and 2 also showed inhibition of angiogenin-induced angiogenesis, as determined by chorioallantoic membrane (CAM) assay. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.06.077

文献信息

• Procyanidin polymers of Douglas fir bark: Structure from degradation with phloroglucinol
  作者：Lai Yeap Foo、Joseph J. Karchesy

  DOI：10.1016/0031-9422(89)80303-6

  日期：1989.1

  Abstract Reaction of the condensed tannin polymers of Douglas fir inner bark with phloroglucinol yielded catechin, epicatechin, procyanidin B-2, catechin-(4α→2)-phloroglucinol, epicatechin-(4β→2)-phloroglucinol, the novel compound epicatechin-(4α→2)-phloroglucinol and 1,3-di (2,4,6-trihydroxyphenyl)-1-(3,4-di-hydroxyphenyl)-propan-2-ol. Also isolated were epicatechin-(4β→8)-epicatechin-(4β→2)-phloroglucinol

  摘要 花旗松内皮的缩合单宁聚合物与间苯三酚反应生成儿茶素、表儿茶素、原花青素 B-2、儿茶素-(4α→2)-间苯三酚、表儿茶素-(4β→2)-间苯三酚、新型化合物表儿茶素-( 4α→2)-间苯三酚和1,3-二(2,4,6-三羟基苯基)-1-(3,4-二-羟基苯基)-丙-2-醇。还分离出了表儿茶素-(4β→8)-表儿茶素-(4β→2)-间苯三酚、表儿茶素-(4β→6)-表儿茶素-(4β→2)-间苯三酚和其他三种新型间苯三酚加合物，儿茶素-(4α →8)-表儿茶素-(4β→2)-间苯三酚、表儿茶素-(4β→8)-表儿茶素-(4β→8)-表儿茶素-(4β→2)-间苯三酚和表儿茶素-(4β→6)-表儿茶素- (4β→8)-表儿茶素-(4β→2)-间苯三酚。结果表明，扩展单元的配置几乎完全是 2,3-顺式，而终端单元则是混合的，有 2, 3-顺式略占优势。C-4 到 C-8 间黄酮连接以 4:1 的比例超过
• Condensed tannins: preferential substitution at the interflavanoid bond by sulphite ion
  作者：L. Yeap Foo、Gerald W. McGraw、Richard W. Hemingway

  DOI：10.1039/c39830000672

  日期：——

  The reaction of loblolly pine (Pinus taeda L.) bark tannins with sodium hydrogen sulphite gave sodium epicatechin-(4β)-sulphonate (1) and sodium epicatechin-(4β→ 8)-epicatechin-(4β)-sulphonate (2) in high yield with only a minor amount of sodium 1-(3,4-dihydroxyphenys)-2-hydroxy-3-(2,4,6-trihdroxyphenyl)-propane-1-sulphonate (3).

  火炬松的反应（火炬松L.）树皮的单宁酸与亚硫酸氢钠，得到钠表儿茶素- （4 β） -磺酸盐（1）和钠表儿茶素（4 β →交通8） -表儿茶素- （4 β） -磺酸盐（2）仅以少量的1-（3,4-二羟基苯基）-2-羟基-3-（2,4,6-三苯氧基苯基）-丙烷-1-磺酸钠（3）高收率。
• Proanthocyanidins from Lotus corniculatus
  作者：L.Y. Foo、R. Newman、G. Waghorn、W.C. McNabb、M.J. Ulyatt

  DOI：10.1016/0031-9422(95)00602-8

  日期：1996.2

  The chemical structure of the purified proanthocyanidin polymers of Lotus corniculatus was analysed by 13C NMR and by mild acid catalysed degradation in the presence of excess of phloroglucinol. The NMR data showed that the polymer was partially glycosidated with a number average Mr in the range 1800–2100 (six to seven flavanoid units). The products from phloroglucinol scission reaction indicated the

  通过 13 C NMR 和在过量间苯三酚存在下的弱酸催化降解分析了莲花的纯化原花色素聚合物的化学结构。NMR 数据显示，聚合物部分糖苷化，平均 Mr 范围为 1800-2100（六到七个类黄酮单元）。间苯三酚裂解反应的产物表明，增量剂黄烷单元主要由表儿茶素 (67%) 和表没食子儿茶素 (30%) 组成，还有少量的儿茶素和表儿茶素单元，它们主要由 C-4/C-8 间黄酮连接在一起债券。聚合物链主要由儿茶素 (83%) 终止，并在较小程度上由表儿茶素 (16%) 终止。
• Oligomeric flavanoids. Part 17. Absolute configurations of flavan-3-ols and 4-arylflavan-3-ols via the Mosher method
  作者：Wanda Rossouw、Alexander F. Hundt、Jacobus A. Steenkamp、Daneel Ferreira

  DOI：10.1016/s0040-4020(01)89554-5

  日期：1994.1

  1H NMR analysis of R-(+)- and S-(−)-α-methoxy-α-trifluoromethylphenyl acetic acid (MTPA) esters of flavan-3-ols and 4-arylflavan-3-ols permits assessment of absolute configurations of C-3 of these condensed tannin structural units.

  flavan-3-ols和4-芳基flavan-3-ols的R -（+）-和S -（-）-α-甲氧基-α-三氟甲基苯基乙酸（MTPA）酯的1 H NMR分析这些缩合的单宁结构单元的C-3中
• METHOD OF PRODUCING PROANTHOCYANIDIN OLIGOMER
  申请人：Tanaka Takashi

  公开号：US20090047305A1

  公开（公告）日：2009-02-19

  The present invention relates to a composition containing as its main component proanthocyanidin oligomer to which a substance having a phloroglucinol ring structure or resorcinol ring structure has been bonded, and reduced in the molecular weight, which is obtained by heating plant materials containing proanthocyanidin polymer or extract thereof with a substance having a phloroglucinol ring structure or resorcinol ring structure in an acidic aqueous solution, production method thereof, and uses of the composition in health products and pharmaceutical products. According to the invention, proanthocyanidin oligomer having physiological activity, to which a substance having a phloroglucinol ring structure or resorcinol ring structure has been bonded and reduced in the molecular weight to such a level that the oligomer can be absorbed into living body, which has been conventionally difficult to obtain at high yield from plant raw materials, can be produced efficiently and easily.

  本发明涉及一种组合物，其主要成分为与具有邻苯二酚环结构或间苯二酚环结构的物质键合并分子量降低的原花青素寡聚体，该组合物通过在酸性水溶液中将含有原花青素聚合物或其提取物的植物材料与具有邻苯二酚环结构或间苯二酚环结构的物质加热而得到，以及该组合物在健康产品和药品中的用途和其制备方法。根据本发明，具有生理活性的原花青素寡聚体，其分子量已经被降低到能够被生物体吸收的水平，并且与具有邻苯二酚环结构或间苯二酚环结构的物质键合，这在以往从植物原材料中高产得到是困难的，现在可以高效、容易地生产。