原花青素C4 | 87727-69-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 中文名称: 原花青素C4
• 英文名称: epicatechin-(4β<*>8)-catechin-(4α<*>8)-catechin
• 英文别名: epicatechin-(4β->8)-catechin-(4α->8)-catechin；epicatechin-(4β→8)-catechin-(4α→8)-catechin；arecatannin C-1；procyanidin C4；epicatechin-(4β[*]8)-catechin-(4α[*]8)-catechin；Arecatannin C1；(2R,3S,4R)-2-(3,4-dihydroxyphenyl)-4-[(2R,3S)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-chromen-8-yl]-8-[(2R,3R,4R)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-chromen-4-yl]-3,4-dihydro-2H-chromene-3,5,7-triol
• CAS: 87727-69-3
• 化学式: C₄₅H₃₈O₁₈
• 分子量: 866.786
• InChiKey: MOJZMWJRUKIQGL-LKMJJRCWSA-N

物化性质

• 密度：
  1.747±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  63
• 可旋转键数：
  5
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  331
• 氢给体数：
  15
• 氢受体数：
  18

反应信息

• 作为反应物：
  描述：

  原花青素C4 在 W-4 Raney Ni 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 4.0h， 生成 原花青素(OPC)
  参考文献：
  名称：

  Tannins from Betel Nuts

  摘要：

  AbstractFrom the acetone extract of fresh‐betel nuts, two procyanidin pentamers, two procyanidin tetramers and three procyanidin trimers, along with (+)‐catechin, (‐)‐epicatechin, procyanidin A‐l, procyanidin B‐l, procyanidin B‐2, and procyanidin B‐7 were isolated. Based on 1H NMR and 13C NMR spectral data as well as the results of thiolysis degradation, the chemical structures of two series of oligomeric arecatannins A and B have been established. The arecatannins from betel nuts were found to be condensed‐type tannins which possess (‐)‐epicatechin unit and (+)‐catechin units. All arecatannins had C4‐C8 linked (‐)‐epicatechin in the upper units whereas the (+)‐catechin in the terminal unit had C4‐C8 or C4‐C6 linkage.

  DOI：

  10.1002/jccs.199600013
• 作为产物：
  描述：

  [4,8:4'',8'']-2,3-cis-3,4-trans: 2'',3''-trans-3'',4''-trans: 2'''',3''''-trans-dodeca-O-benzyl-(-)-epicatechin-(+)-catechin-(+)-catechin 在 palladium dihydroxide 氢气 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 2.0h， 以100%的产率得到原花青素C4
  参考文献：
  名称：

  Systematic synthesis of four epicatechin series procyanidin trimers and their inhibitory activity on the Maillard reaction and antioxidant activity

  摘要：

  A systematic synthesis of four natural epicatechin series procyanidin trimers 1[4,8:4",8"]-2,3-cis-3,4-trans: 2",3"-cis-3",4"-trans: 2"",3""-trans-(-)-epi-catechin-(-)-epicatechin-(+)-catechin, [4,8:4",8"]-2,3-cis-3,4-trans: 2",3"-cis-3",4"-trans: 2"",3""-cis-tri(-)-epicatechin: procyanidin C1, [4,8:4",8"]-2,3-cis-3,4-trans: 2",3"-trans-3",4"-trans: 2"",3""-trans-(-)-epicatechin-(+)-catechin-(+)-catechin: procyanidin C4, and [4,8:4",8"]-2,3-cis-3,4-trans: 2",3"-trans-3",4"-trans: 2"",3""-cis-(-)-epicatechin-(+)-catechin-(-)-epicatechin is described. Condensation of (2R,3R,4S)-5,7,3'4'-tetra-O-benzyl-4-(2"-ethoxyethyloxy)flavan derived from (-)-epicatechin as an electrophile with the dimeric nucleophiles in the presence of TMSOTf followed by deprotection yielded trimers. Inhibitory activities on the Maillard reaction and antioxidant activity on lipid peroxide of the synthesized oligomers were also investigated. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.07.024

文献信息

• 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。
• Flavan-3-ols and procyanidins from the bark of Salix purpurea L.
  作者：Juergenliemk、Petereit、Nahrstedt, Adolf

  DOI：10.1691/ph.2007.3.6577

  日期：——

  From a commercial aqueous ethanolic extract obtained from the bark of Salix purpurea L. the flavan-3-ols catechin, epicatechin, gallocatechin, catechin-3-O-(1-hydroxy-6-oxo-2-cyclohexene-1-carboxylic acid)-ester, the dimeric procyanidins B1, B3 and the trimeric procyanidins epicatechin-(4β→8)-catechin-(4α→8)-catechin and epicatechin-(4β→8)-epicatechin-(4β→8)-catechin were isolated. Structure elucidation was performed by NMR, CD, MS, degradation and optical rotation methods. A fraction containing higher oligomeric procyanidins was investigated by 13C NMR. Data indicate an average degree of oligomerization of 4 to 5 flavan-3-ol units with dihydroxylated B-rings and predominance of 2,3-cis-stereochemistry.

  从从 Salix purpurea L. 的树皮中获得的市售水乙醇提取物中，黄烷-3-醇儿茶素、表儿茶素、没食子儿茶素、儿茶素-3-O-(1-羟基-6-氧代-2-环己烯-1-羧酸) )-酯，二聚原花青素 B1、B3 和三聚原花青素表儿茶素-(4β→8)-儿茶素-(4α→8)-儿茶素和表儿茶素-(4β→8)-表儿茶素-(4β→8)-儿茶素孤立。通过NMR、CD、MS、降解和旋光方法进行结构解析。通过 13C NMR 研究了含有高级低聚原花青素的级分。数据表明，具有二羟基化 B 环的 4 至 5 个黄烷-3-醇单元的平均低聚度和 2,3-顺式立体化学占主导地位。
• 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
• Acylated flavanols and procyanidins from Salix sieboldiana
  作者：Feng-Lin Hsu、Gen-Ichiro Nonaka、Itsuo Nishioka

  DOI：10.1016/s0031-9422(00)83128-3

  日期：1985.1
• Systematic synthesis of four epicatechin series procyanidin trimers and their inhibitory activity on the Maillard reaction and antioxidant activity
  作者：Akiko Saito、Yuki Doi、Akira Tanaka、Nobuyasu Matsuura、Makoto Ubukata、Noriyuki Nakajima

  DOI：10.1016/j.bmc.2004.07.024

  日期：2004.9

  A systematic synthesis of four natural epicatechin series procyanidin trimers 1[4,8:4",8"]-2,3-cis-3,4-trans: 2",3"-cis-3",4"-trans: 2"",3""-trans-(-)-epi-catechin-(-)-epicatechin-(+)-catechin, [4,8:4",8"]-2,3-cis-3,4-trans: 2",3"-cis-3",4"-trans: 2"",3""-cis-tri(-)-epicatechin: procyanidin C1, [4,8:4",8"]-2,3-cis-3,4-trans: 2",3"-trans-3",4"-trans: 2"",3""-trans-(-)-epicatechin-(+)-catechin-(+)-catechin: procyanidin C4, and [4,8:4",8"]-2,3-cis-3,4-trans: 2",3"-trans-3",4"-trans: 2"",3""-cis-(-)-epicatechin-(+)-catechin-(-)-epicatechin is described. Condensation of (2R,3R,4S)-5,7,3'4'-tetra-O-benzyl-4-(2"-ethoxyethyloxy)flavan derived from (-)-epicatechin as an electrophile with the dimeric nucleophiles in the presence of TMSOTf followed by deprotection yielded trimers. Inhibitory activities on the Maillard reaction and antioxidant activity on lipid peroxide of the synthesized oligomers were also investigated. (C) 2004 Elsevier Ltd. All rights reserved.