4-benzylsulfanylcatechin | 698998-85-5

• 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: 4-benzylsulfanylcatechin
• 英文别名: 4-benzylthioether of catechin；benzylthiocatechin；catechin 4-benzylthioether；catechin-benzthiol ether；(2R,3R)-4-benzylsulfanyl-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-chromene-3,5,7-triol
• CAS: 698998-85-5
• 化学式: C₂₂H₂₀O₆S
• 分子量: 412.463
• InChiKey: YYEFTOIQHQHUQZ-JAZPPYFYSA-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：

  4-benzylsulfanylcatechin 在 silver tetrafluoroborate 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 原花青素C2
  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：

  苄硫醇 、 花旗松素 在 sodium tetrahydroborate 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 12.0h， 生成 4-benzylsulfanylcatechin
  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

文献信息

• Polyphenolic compounds from Croton lechleri
  作者：Y. Cai、F.J. Evans、M.F. Roberts、J.D. Phillipson、M.H. Zenk、Y.Y. Gleba

  DOI：10.1016/0031-9422(91)85063-6

  日期：1991.1

  The blood-red sap of Croton lechleri was found to contain proanthocyanidins as major constituents which accounted for up to 90% of the dried weight. In addition to (+)-catechin, (−)-epicatechin, (+)-gallocatechin, (−)-epigallocatechin and dimeric procyanidins B-1 and B-4, five novel dimers and trimers were isolated and characterized as catechin-(4α→8)- epigallocatechin, gallocatechin-(4α→8)-epicatechin

  巴豆的血红色汁液被发现含有原花青素作为主要成分，占干重的 90%。除了 (+)-儿茶素、(-)-表儿茶素、(+)-没食子儿茶素、(-)-表没食子儿茶素和二聚体原花青素 B-1 和 B-4 外，还分离了五种新型二聚体和三聚体，并将其表征为儿茶素-( 4α→8)-表没食子儿茶素、没食子儿茶素-(4α→8)-表儿茶素、没食子儿茶素-(4α→6)-表没食子儿茶素、儿茶素-(4α→8)-没食子儿茶素-(4α→8)-没食子儿茶素和没食子儿茶素-(4α→) 8)-没食子儿茶素-(4α→8)-表没食子儿茶素。还获得了更高的低聚物。已开发出一种将化学降解与 1 H NMR 光谱相结合的新程序，用于测定低聚/聚合原花色素的组成和分子大小。树液低聚物的平均聚合度分别为 4,5-6 和 6-7，Mr 高达 2130。各种黄烷的存在清楚地表明了低聚物的异质性。 3-ols 作为扩展和终端单元。在低聚物中观察到异常高含量的没食子儿茶素和表没食子儿茶素。
• Synthesis of dimeric, trimeric, tetrameric pentameric, and higher oligomeric epicatechin-derived procyanidins having 4beta,8-interflavan linkages and their use to inhibit cancer cell growth through cell cycle arrest
  申请人：——

  公开号：US20040116718A1

  公开（公告）日：2004-06-17

  Various processes are disclosed for preparing protected epicatechin oligomers having (4&bgr;,8)-interflavan linkages. In one process, a tetra-O-protected epicatechin monomer or oligomer is coupled with a protected, C-4 activated epicatechin monomer in the presence of an acidic clay such as a mortmorillonite clay. In another process, a 5,7,3′,4′-benzyl protected or a 3-acetyl-, 5,7,3′,4′-benzyl protected epicatechin or catechin monomer or oligomer is reacted with 3-O-acetyl-4-[(2-benzothiazolyl)thio]-5,7,3′,4′-tetra-O-benzylepicatechin in the presence of silver tetrafluoroborate. In another process, two 5,7,3′,4′-benzyl protected epicatechin monomers activated with 2-(benzothiazolyl)thio groups at the C-4 positions are cross-coupled in the presence of silver tetrofluoroborate. A process is also disclosed for reacting an unprotected epicatechin or catechin monomer with 4-(benzylthio) epicatechin or catechin. The use of naturally-derived and synthetically-prepared procyanidin (4&bgr;,8) 4 -pentamers to treat cancer is also disclosed.

  揭示了多种制备具有（4'，8）-交互缬氨酸连接的受保护表儿茶素寡聚物的过程。在一种过程中，通过在存在酸性粘土（如蒙脱石粘土）的情况下，将四重受保护的表儿茶素单体或寡聚体与受保护的C-4活化的表儿茶素单体偶联。在另一种过程中，通过在存在四氟硼酸银的情况下，将5,7,3′,4′-苄基保护或3-乙酰基-，5,7,3′,4′-苄基保护的表儿茶素或儿茶素单体或寡聚体与3-O-乙酰基-4-[（2-苯并噻唑基）硫]-5,7,3′,4′-四重苄基表儿茶素反应。在另一种过程中，两个在C-4位置激活了2-（苯并噻唑基）硫基团的5,7,3′,4′-苄基保护表儿茶素单体交叉偶联，在四氟硼酸银的存在下。还揭示了一种过程，用于将未受保护的表儿茶素或儿茶素单体与4-（苄硫基）表儿茶素或儿茶素反应。还揭示了使用天然衍生和合成制备的（4'，8）4-五聚体前花青素来治疗癌症。
• Flavan-3-ol and procyanidin glycosides from quercus miyagii
  作者：Kanji Ishimaru、Gen-Ichiro Nonaka、Itsuo Nishioka

  DOI：10.1016/s0031-9422(00)82371-7

  日期：1987.1

  Abstract A chemical examination of the leaves and bark of Quercus miyagii has led to the isolation and characterization of two flavan-3-ol glycosides and two procyanidin rhamnosides in which the sugar residue is located at C-3.

  摘要 通过对宫城栎叶和树皮的化学检测，分离和表征了两种 flavan-3-ol 苷和两种原花青素鼠李糖苷，其中糖残基位于 C-3。
• Polyphenols from peanut skins and their free radical-scavenging effects
  作者：Hongxiang Lou、Huiqing Yuan、Bin Ma、Dongmei Ren、Mei Ji、Syuichi Oka

  DOI：10.1016/j.phytochem.2004.06.026

  日期：2004.8

  catalyzed degradation, their structures were determined to be epicatechin-(2beta-->O -->7, 4beta -->6)-[epicatechin-(4beta-->8)]-catechin (1), epicatechin-(2beta-->O -->7, 4beta-->8) epicatechin-(4beta-->8)-catechin-(4alpha-->8)-epicatechin (2), and procyanidins B2 (3), B3 (4) and B4 (5). The absolute configuration of the new compounds was determined from their circular dichroism curves and the (1)H NMR spectra

  花生皮水溶性部分的分离导致了五种原花色素的分离。基于光谱研究和部分酸催化降解，它们的结构被确定为表儿茶素-(2beta-->O -->7, 4beta -->6)-[epicatechin-(4beta-->8)]-catechin (1), 表儿茶素-(2beta-->O -->7, 4beta-->8) 表儿茶素-(4beta-->8)-儿茶素-(4alpha-->8)-表儿茶素 (2), 和原花青素B2 (3)、B3 (4) 和 B4 (5)。新化合物的绝对构型是由它们的圆二色性曲线和 (1) H NMR 光谱确定的，在手性二铑配合物（四氢二铑）存在下通过硫解降解 1 和 2 形成的 flavan-3-ols (R)-(三氟甲基)苯乙酸酯)。
• Tannins and related compounds. XXXIII. Isolation and characterization of procyanidins in Dioscorea cirrhosa Lour.
  作者：FENGLIN HSU、GENICHIRO NONAKA、ITSUO NISHIOKA

  DOI：10.1248/cpb.33.3293

  日期：——

  Dimeric, trimeric and tetrameric procyanidins have been isolated, together with (+)-catechin (1) and (-)-epicatechin (2), from the tubers of Dioscorea cirrhosa LOUR. (Dioscoreaceae). By comparisons of the physical and spectral data, the dimers (3-5), trimers (6-8) and tetramer (9) were identified as procyanidins obtained previously. The structures of two other trimers (10 and 11) were established by acid-catalyzed thiolytic degradation, while the formation of the tetramer (12) by condensation of the 4-carbocation of 1 with 6, in conjunction with 1H- and 13C-nuclear magnetic resonance examinations, established the structure of 12.

  从薯蓣科植物薯蓣（Dioscorea cirrhosa LOUR.）的块茎中分离出二聚体、三聚体和四聚体原花青素，以及(+)-儿茶素(1)和(-)-表儿茶素(2)。(薯蓣科）块茎中分离出来。通过物理和光谱数据的比较，二聚体（3-5）、三聚体（6-8）和四聚体（9）被确定为之前获得的原花青素。另外两种三聚体（10 和 11）的结构是通过酸催化硫解作用确定的，而四聚体（12）是通过 1 与 6 的 4-配位缩合形成的，结合 1H 和 13C 核磁共振检查，确定了 12 的结构。