procyanidin B-1 | 660832-10-0

• 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: procyanidin B-1
• 英文别名: (2R,3S)-2-(3,4-dihydroxyphenyl)-8-[(2R,3R)-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: 660832-10-0
• 化学式: C₃₀H₂₆O₁₂
• 分子量: 578.529
• InChiKey: XFZJEEAOWLFHDH-PXAFTKFOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  42
• 可旋转键数：
  3
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  221
• 氢给体数：
  10
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  procyanidin B-1 、 聚合甲醛 生成 [(2R,3S)-2-(3,4-dihydroxyphenyl)-8-[(2R,3R)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-6,8-bis(sulfonatomethyl)-3,4-dihydro-2H-chromen-4-yl]-3,5,7-trihydroxy-3,4-dihydro-2H-chromen-6-yl]methanesulfonate
  参考文献：
  名称：

  MCGRAW, GERALD W.;LAKS, PETER E.;HEMINGWAY, RICHARD W., J. WOOD CHEM. AND TECHNOL., 8,(1988) N 1, 91-109

  摘要：

  DOI：
• 作为产物：
  描述：

  [4,8]-2,3-cis-3,4-trans-2”,3”-trans-3,5,7,3’4’-penta-O-acetyl-5”,7”,3”’,4”’-tetra-O-benzyl-(-)-epicatechin-(+)-catechin 在 potassium carbonate 、 10 wt% Pd(OH)2 on carbon 作用下， 以 甲醇 、 二氯甲烷 、 四氢呋喃 、 水 为溶剂， 反应 0.5h， 以56%的产率得到procyanidin B-1
  参考文献：
  名称：

  Development of a New Synthetic Strategy for Procyanidin Dimer Condensation Using Peracetylated Electrophiles

  摘要：

  Proanthocyanidins, also known as condensed tannins and/or oligomeric flavonoids, are found in many edible plants and show interesting various biological activities. We report a simple new proanthocyanidin synthesis strategy in which an electrophile derived from a flavan-3-ol peracetate is condensed with 1.5 eq. of a benzylated nucleophile. We demonstrate here the synthesis of procyanidin B1, a (-)-epicatechin-(4 beta-8)-(+)-catechin dimer, to demonstrate the utility of this method. This strategy is applicable for the synthesis of various commercially available flavan-3-ol and various oligomeric flavonoids.

  DOI：

  10.3987/com-13-s(s)103

文献信息

• Processes for the preparation of protected-(+)-catechin and (-)-epicatechin monomers, for coupling the protected monomers with an activated, protected epicatechin monomer, and for the preparation of epicatechin-(4B,8)-epicatechin or -catechin dimers and their digallates
  申请人：Romanczyk Leo

  公开号：US20070004796A1

  公开（公告）日：2007-01-04

  Improved processes for the preparation of tetra-O-benzyl protected catechin, for the coupling of the tetra-O-benzyl protected catechin or epicatechin with a C-4 activated, tetra-O-benzyl protected epicatechin for the galloylation of the epicatechin-(4β,8)-catechin or -epicatechin dimer-the dimer digallates, and for the deprotection (i.e., debenzylation) of the protected epicatechin dimers and protected epicatechin dimer digallates are disclosed.

  揭示了用于制备四重O-苄基保护的儿茶素的改进工艺，用于将四重O-苄基保护的儿茶素或表儿茶素与C-4活化的四重O-苄基保护的表儿茶素偶联以进行表儿茶素-(4β,8)-儿茶素或-表儿茶素二聚体的没食子酸化，以及用于去保护（即去苄基化）保护的表儿茶素二聚体和保护的表儿茶素二聚体二没食子酸酯的工艺。
• ARIGA, TOSHIAKI;KOSHIYAMA, IKUNORI;FUKUSHIMA, DANJI, AGR. AND BIOL. CHEM., 52,(1988) N1, C. 2717-2722
  作者：ARIGA, TOSHIAKI、KOSHIYAMA, IKUNORI、FUKUSHIMA, DANJI

  DOI：——

  日期：——
• Synergistic Pharmaceutical And/Or Neutraceutical Flavanoid Composition For Management Of Diabetes Mellitus
  申请人：Bhaskaran Sunil

  公开号：US20070219146A1

  公开（公告）日：2007-09-20

  The present invention relates to a synergistic pharmaceutical and/or neutraceutical flavanoid composition for management of Diabetes Mellitus, said composition comprising polyphenol of concentration ranging between 85 to 95% (w/w) GAE, theobromine of concentration ranging between 1 to 5% (w/w), and moisture content ranging between 0.5 to 10% (v/w).