4β-benzylthioepicatechin | 37064-35-0

• 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: 4β-benzylthioepicatechin
• 英文别名: (2R,3S,4S)-4-benzylthioflavan-3,5,7,3',4'-pentaol；epicatechin-(4β->S)-benzylthioether；(-)-epicatechin 4-β-benzylthioether；(-)-epicatechin 4β-benzylthioether；(-)-epicatechin-4β-benzylthioether；epicatechin-(4β-S)-benzylthioether；(2R,3S,4S)-4-benzylsulfanyl-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-chromene-3,5,7-triol
• CAS: 37064-35-0
• 化学式: C₂₂H₂₀O₆S
• 分子量: 412.463
• InChiKey: YYEFTOIQHQHUQZ-BDTNDASRSA-N

物化性质

• 沸点：
  707.7±60.0 °C(Predicted)
• 密度：
  1.56±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  136
• 氢给体数：
  5
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4β-benzylthioepicatechin 、 儿茶提取物 在 silver tetrafluoroborate 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以38%的产率得到原花青素(OPC)
  参考文献：
  名称：

  Oligomeric flavanoids. Part 27. Interflavanyl bond formation in procyanidins under neutral conditions

  摘要：

  Dimethyl(methylthio)sulfonium tetrafluoroborate (DMTSF) and silver tetrafluoroborate (AgBF4) activate the CI-S bond in the Lt-thioethers of flavan-3-ols toward carbon nucleophiles to permit formation of the interflavanyl bond in procyanidins under neutral conditions. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00454-2
• 作为产物：
  描述：

  epicatechin-(4β->8)-epiafzelechin 在 溶剂黄146 、 苄硫醇 作用下， 以 乙醇 为溶剂， 反应 8.0h， 以8 mg的产率得到4β-benzylthioepicatechin
  参考文献：
  名称：

  Morimoto, Satoshi; Nonaka, Gen-Ichiro; Chen, Rong-Fu, Chemical and pharmaceutical bulletin, 1988, vol. 36, # 1, p. 39 - 47

  摘要：

  DOI：

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
• Plant proanthocyanidins. Part 7. Prodelphinidins from Pinus sylvestris
  作者：Raj K. Gupta、Edwin Haslam

  DOI：10.1039/p19810001148

  日期：——

  A dimeric prodelphinidin and a polymeric proanthocyanidin have been isolated from male flowers of Pinus sylvestris. Structural analyses of the dimer and the polymer are reported and a biomimetic synthesis of the dimer is noted.

  从樟子松（Pinus sylvestris）的雄花中分离到了二聚前地黄素和聚合原花青素。报告了对二聚体和聚合物的结构分析，并指出了对二聚体的仿生合成。
• Tannins and related compounds. XXXI. Isolation and characterization of proanthocyanidins in Kandelia candel (L.) Druce.
  作者：FENGLIN HSU、GENICHIRO NONAKA、ITSUO NISHIOKA

  DOI：10.1248/cpb.33.3142

  日期：——

  Together with propelargonidin dimers (14, 15 and 16), and procyanidin trimers (23, 24 and 25) of common types, two novel proanthocyanidin dimers, kandelins A-1 (12) and A-2 (13), and four trimers, kandelins B-1 (19), B-2 (20), B-3 (21) and B-4 (22), which all contain a phenylpropanoid substituent in the upper flavan unit, have been isolated from the bark of Kandelia candel (L.) DRUCE (Rhizophoraceae). Spectroscopic evidence combined with chemical studies involving acid-catalyzed thiolytic degradation permitted the assignment of their structures. The presence in this plant source of flavan-3-ols, (+)-afzelechin (2), (+)-catechin (3), (-)-epicatechin (4) and (+)-gallocatechin (5), known proanthocyanidins B-1 (8), B-2 (9), C-1 (17) and trimer (18), and cinchonains Ia (6), Ib (7), IIa (10) and IIb (11) was also demonstrated.

  除了常见类型的丙炔苷二聚体（14、15 和 16）和原花青素三聚体（23、24 和 25）外，还有两种新型原花青素二聚体，即蒲公英苷 A-1 (12)和 A-2 (13)，以及四种三聚体、从 Kandelia candel (L.) DRUCE（根状茎）的树皮中分离出了四种三聚体，即蒲公英素 B-1 (19)、B-2 (20)、B-3 (21) 和 B-4 (22)，它们都在上部黄烷单元中含有一个苯基丙酮取代基。DRUCE）（Rhizophoraceae）树皮中分离出来。光谱证据与酸催化硫解降解的化学研究相结合，确定了它们的结构。此外，还证明了该植物来源中存在黄烷-3-醇、(+)-阿夫茶精（2）、(+)-儿茶素（3）、(-)-表儿茶素（4）和(+)-儿茶素（5），已知的原花青素 B-1 (8)、B-2 (9)、C-1 (17) 和三聚体 (18)，以及金鸡纳素 Ia (6)、Ib (7)、IIa (10) 和 IIb (11)。
• 4-Carboxymethyl flavan-3-ols and procyanidins from Davallia divaricata
  作者：Tieh-Horng Hwang、Yoshiki Kashiwada、Gen-ichiro Nonaka、Itsuo Nishioka

  DOI：10.1016/0031-9422(90)89050-j

  日期：1990.1

  Abstract A series of flavan-3-ols and procyanidins, possessing a carboxymethyl group, and a procyanidin tetramer have been isolated from the fern, Davallia divaricata . The structures were characterized on the basis of chemical and spectral evidence.

  摘要 从蕨类植物Davallia divaricata 中分离得到一系列具有羧甲基的黄烷醇和原花青素以及原花青素四聚体。基于化学和光谱证据表征结构。
• Studies on the Constituents of Bark of Parameria laevigata Moldenke.
  作者：Kohei KAMIYA、Chiharu WATANABE、Hanani ENDANG、Mansur UMAR、Toshiko SATAKE

  DOI：10.1248/cpb.49.551

  日期：——

  One new trimeric proanthocyanidin, epicatechin-(2β→O→7, 4β→6)-epicatechin-(2β→O→7, 4β→8)-epicatechin (5) and two new tetrameric proanthocyanidins, epicatechin-(2β→O→7, 4β→8)-[epicatechin-(4β→6)]-epicatechin-(4β→8)-epicatechin, named as parameritannin A-1 (6), and epicatechin-(2β→O→5, 4β→6)-[epicatechin-(2β→O→7, 4β→8)]-epicatechin-(4β→8)-epicatechin, named as parameritannin A-2 (7), have been isolated from the bark of Parameria laevigata Moldenke (Apocynaceae) along with the two known dimers, proanthocyanidin A-2 (1) and proanthocyanidin A-6 (2), and two trimers, cinnamtannin B-1 (3) and aesculitannin B (4). These structures were elucidated by spectral and chemical evidence.

  一种新的三聚原花青素，表儿茶素-(2β→O→7，4β→6)-表儿茶素-(2β→O→7，4β→8)-表儿茶素(5)和两种新的四聚原花青素、表儿茶素-(2β→O→7, 4β→8)-[表儿茶素-(4β→6)]-表儿茶素-(4β→8)-表儿茶素，被命名为副花青素 A-1 (6)，以及表儿茶素-(2β→O→5、表儿茶素-(2β→O→7, 4β→8)]-表儿茶素-(4β→8)-表儿茶素，被命名为副花色单宁 A-2（7）、原花青素 A-2 (1) 和原花青素 A-6 (2)，以及两种三聚体肉桂单宁 B-1 (3) 和茎叶单宁 B (4)。这些结构通过光谱和化学证据得以阐明。