catechin-(4α->S)-benzylthioether | 72448-81-8

• 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: catechin-(4α->S)-benzylthioether
• 英文别名: catechin-(4α-S)-benzylthioether；4α-benzylsulfanylcatechin；(+)-catechin 4-benzylthioether；4α-benzylthiocatechin；(2R,3R,4R)-4-benzylsulfanyl-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-chromene-3,5,7-triol
• CAS: 72448-81-8
• 化学式: C₂₂H₂₀O₆S
• 分子量: 412.463
• InChiKey: YYEFTOIQHQHUQZ-YPAWHYETSA-N

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

• 作为产物：
  描述：

  (2R,2''R,3S,3''R,4S)-[4,8]-2,3-trans-3,4-trans-(+)-catechin-(-)-epigallocatechin 、 苄硫醇 生成 catechin-(4α->S)-benzylthioether
  参考文献：
  名称：

  HASHIMOTO, FUMIO;NONAKA, GEN-ICHIRO;NISHIOKA, ITSUO, CHEM. AND PHARM. BULL., 37,(1989) N, C. 77-85

  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
• 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。
• Prenylated flavan-3-ols and procyanidins from Illicium anisatum
  作者：Satoshi Morimoto、Hisako Tanabe、Gen-Ichiro Nonaka、Itsuo Nishioka

  DOI：10.1016/0031-9422(88)84117-7

  日期：1988.1

  Abstract Two prenylated flavan-3-ols were isolated from Illicium anisatum and their structures characterized by chemical and spectroscopic means as 8-(3,3-dimethylallyl)-(+)-catechin and 6-(3,3-dimethylallyl)-(+)-catechin. In addition, a new proanthocyanidin was isolated, together with several known compounds. The structure of the procyanidin was established as catechin-(4α→8)-epicatechin-(4β→8)-catechin

  摘要 从八角茴香中分离出两种异戊二烯化黄烷-3-醇，通过化学和光谱学手段对其结构表征为8-(3,3-二甲基烯丙基)-(+)-儿茶素和6-(3,3-二甲基烯丙基)-( +)-儿茶素。此外，还分离出了一种新的原花青素以及几种已知的化合物。原花青素的结构确定为儿茶素-(4α→8)-表儿茶素-(4β→8)-儿茶素。
• Hashimoto, Fumio; Nonaka, Gen-ichiro; Nishioka, Itsuo, Chemical and pharmaceutical bulletin, 1989, vol. 37, # 1, p. 77 - 85
  作者：Hashimoto, Fumio、Nonaka, Gen-ichiro、Nishioka, Itsuo

  DOI：——

  日期：——
• Procyanidin dimers and trimers from Douglas fir inner bark
  作者：Lai Yeap Foo、Joseph J. Karchesy

  DOI：10.1016/s0031-9422(00)97836-1

  日期：1989.1