(-)-epicatechin-(2β→O→7,4β→8)-(-)-catechin | 111466-29-6

• 物质功能分类: 分析化学 - 标准品
• 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: (-)-epicatechin-(2β→O→7,4β→8)-(-)-catechin
• 英文别名: (-)-epicatechin-(2β→7,4β→8)-(-)-catechin；proanthocyanidin A-4；proanthocyanidin A₄；Proanthocyanidin A4；(1R,5S,6R,13S,21R)-5,13-bis(3,4-dihydroxyphenyl)-4,12,14-trioxapentacyclo[11.7.1.02,11.03,8.015,20]henicosa-2(11),3(8),9,15,17,19-hexaene-6,9,17,19,21-pentol
• CAS: 111466-29-6
• 化学式: C₃₀H₂₄O₁₂
• 分子量: 576.513
• InChiKey: NSEWTSAADLNHNH-IVJIMCHNSA-N

物化性质

• 沸点：
  946.0±65.0 °C(Predicted)
• 密度：
  1.766±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  42
• 可旋转键数：
  2
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  210
• 氢给体数：
  9
• 氢受体数：
  12

安全信息

• WGK Germany：
  3

制备方法与用途

生物活性

Proanthocyanidin A4 是从玉叶金花根部分离出来的一种多酚，广泛存在于多种植物中。研究显示，Proanthocyanidin A4 具有显著的抗炎作用。

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 (-)-epicatechin-(2β→O→7,4β→8)-(-)-catechin 在 吡啶 作用下， 生成 proanthocyanidin A-4 nona-acetate
  参考文献：
  名称：

  A-type Proanthocyanidins from stem-bark of Pavetta owariensis

  摘要：

  In a chemical investigation on the stem-bark of Pavetta owariensis, a new proanthocyanidin A-type, ent-epicatechin (4-alpha --> 8,2-alpha --> O --> 7)-ent-catechin designated as pavetannin A1, was isolated as second representative of a (2-alpha, 4-alpha) A-type proanthocyanidin. Additionally, the occurrence of (+)-catechin, (-)-epicatechin, ent-epicatechin, proanthocyanidin A-2 and proanthocyanidin A-4 was demonstrated, the latter being reported from a natural source for the second time.

  DOI：

  10.1016/0031-9422(91)84150-q
• 作为产物：
  描述：

  procyanidin A2 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 0.17h， 以450 mg的产率得到(-)-epicatechin-(2β→O→7,4β→8)-(-)-catechin
  参考文献：
  名称：

  Nonaka, Gen-Ichiro; Morimoto, Satoshi; Kinjo, Jun-Ei, Chemical and pharmaceutical bulletin, 1987, vol. 35, # 1, p. 149 - 155

  摘要：

  DOI：

文献信息

• Oligomeric flavanoids. Part W. base-catalyzed pyran rearrangements of procyanidin B-2, and evidence for the oxidative transformation of B- to A-type procyanidins
  作者：Johann F.W. Burger、Herbert Kolodziej、Richard W. Hemingway、Jan P. Steynberg、Desmond A. Young、Daneel Ferreira

  DOI：10.1016/s0040-4020(01)87771-1

  日期：1990.1

  Procyanidin B-2 is subject to facile C-ring isomerizations in 0.1M NaHCO3 solution to form a novel series of 3,4,9, 10-tetrahydro-2H, 8-pyrano[2,3-h]chromenes , , and . The low percentage conversion of B- to A-type procyanidin is rationalized in terms of an initial oxidative removal of hydride ion at C-2 (C-ring).

  原花色素B-2是受在0.1M的NaHCO容易C-环异构化3溶液中以形成一种新的一系列的3,4,9,10-四氢-2- ħ，8吡喃并[2,3- ħ ]色烯，，和。从最初在C-2（C环）处氧化氢离子的氧化作用，可以合理地将B-型原花青素转化为A-型原花青素的比例很低。
• Methods to isolate anti-microbials from fruit or seed extracts
  申请人：WiSys Technology Foundation, Inc.

  公开号：US11357811B2

  公开（公告）日：2022-06-14

  The invention provides a method of isolating one or more compounds present in fruit juice or seed extracts that have anti-microbial activity.

  本发明提供了一种方法，用于从果汁或籽提取物中分离出一种或多种具有抗微生物活性的化合物。
• Morimoto, Satoshi; Nonaka, Gen-ichiro; Nishioka, Itsuo, Chemical and pharmaceutical bulletin, 1987, vol. 35, # 12, p. 4717 - 4729
  作者：Morimoto, Satoshi、Nonaka, Gen-ichiro、Nishioka, Itsuo

  DOI：——

  日期：——
• Procyanidin A2 and Its Degradation Products in Raw, Fermented, and Roasted Cocoa
  作者：Cédric De Taeye、Gilles Caullet、Victor Jos Eyamo Evina、Sonia Collin

  DOI：10.1021/acs.jafc.6b05262

  日期：2017.3.1

  Cocoa is known as an important source of flavan-3-ols, but their fate "from the bean to the bar" is not yet clear. Here, procyanidin A2 found in native cocoa beans (9-13 mg/kg) appeared partially epimerized into A2(E1) through fermentation, whereas a second epimer (A2(E2)) emerged after roasting. At m/z 575, dehydrodiepicatechin A was revealed to be the major HPLC peak before fermentation, whereas F1, a marker of well-conducted fermentations, becomes the most intense after roasting.RP-HPLC-ESI(-)-HRMS/MS analysis performed on a procyanidin A2 model medium after 12 h at 90 degrees C revealed many more degradation products than those identified in fermented cocoa, including the last epimer of A2, A2 open structure intermediates (m/z 577), and oxidized A -type dimers (m/z 573).
• METHODS TO ISOLATE ANTI-MICROBIALS FROM FRUIT OR SEED EXTRACTS
  申请人：Wisconsin Alumni Research Foundation

  公开号：US20140004214A1

  公开（公告）日：2014-01-02

  The invention provides a method of isolating one or more compounds present in fruit juice or seed extracts that have anti-microbial activity.