(2R,3S)-8-bromo-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-chromene-3,5,7-triol | 88489-00-3

• 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: (2R,3S)-8-bromo-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-chromene-3,5,7-triol
• CAS: 88489-00-3
• 化学式: C₁₅H₁₃BrO₆
• 分子量: 369.169
• InChiKey: QYFXGKOAAJLYBV-GXTWGEPZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  110
• 氢给体数：
  5
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2R,3S)-8-bromo-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-chromene-3,5,7-triol 在 吡啶 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 48.0h， 生成 3-O-acetyl-8-bromo-3',4',5,7-tetra-O-methyl-(+)-catechin
  参考文献：
  名称：

  Kolodziej, Herbert; Ferreira, Daneel; Roux, David G., Journal of the Chemical Society. Perkin transactions I, 1984, # 3, p. 343 - 350

  摘要：

  DOI：
• 作为产物：
  描述：

  2H-1-benzopyran,3,4-dihydro-2-[3,4 bis[(trimethylsilyl)oxy]phenyl] 生成 (2R,3S)-8-bromo-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-chromene-3,5,7-triol
  参考文献：
  名称：

  BALLENEGGER, M. E.;RIMBAULT, C. G.;ALBERT, A. I.;WEITH, A. J.;COURBAT, P.+

  摘要：

  DOI：

文献信息

• [EN] SYNTHETIC METHODS FOR POLYPHENOLS<br/>[FR] PROCEDES SYNTHETIQUES DE PRODUCTION DE POLYPHENOLS
  申请人：MARS INCORPORATED

  公开号：WO1999019319A1

  公开（公告）日：1999-04-22

  (EN) A process is disclosed for the production of polyphenol oligomers having n polyphenol monomeric units, n being an integer from 2-18. The process includes coupling of a protected polyphenol, having protected phenolic hydroxyl groups, which a C-4 functionalized polyphenol monomer. The protected polyphenol may be a protected polyphenol monomer or a protected polyphenol oligomer having 2-17 monomeric units. Advantageously, polyphenol monomeric units forming the polyphenol oligomers may be the same or different flavanoid compounds.(FR) L'invention concerne un procédé de production d'oligomères polyphénoliques possédant n motifs monomères de polyphénol, n représentant un entier compris entre 2 et 18. Le procédé consiste à coupler un polyphénol protégé, comportant des groupes hydroxyles phénoliques protégés, avec un monomère polyphénolique fonctionnalisé C-4. Le polyphénol protégé peut être un monomère polyphénolique protégé ou un oligomère polyphénolique protégé possédant 2 à 17 motifs monomères. Pour plus d'efficacité, les motifs monomères polyphénoliques formant les oligomères polyphénoliques peuvent être les mêmes ou peuvent être différents de composés flavonoïdes.

  该方法用于生产具有n个聚合物单元的多酚寡聚体，其中n是2-18的整数。该方法包括将具有保护酚羟基的保护多酚与具有C-4功能化的多酚单体偶联。保护多酚可以是具有2-17个单体单元的保护多酚单体或保护多酚寡聚体。有利地，形成多酚寡聚体的多酚单体单元可以是相同或不同的类黄酮化合物。
• Food products having enhanced cocoa polyphenol content
  申请人：Mars Incorporated

  公开号：EP2090177A1

  公开（公告）日：2009-08-19

  The invention provides a dry cocoa mix having conserved concentrations of polyphenols, and in particular cocoa polyphenols. The method of this invention avoids the significant and detrimental polyphenol losses that occur during conventional manufacture by controlling the handling of ingredients in the batching process to provide a product containing a significant amount of the cocoa polyphenols present in the raw materials used to formulate the finished product. The cocoa polyphenol containing ingredient is partially defatted cocoa solids.

  本发明提供一种干可可混合物，其多酚，特别是可可多酚的浓度保持不变。本发明的方法通过控制配料过程中配料的处理，避免了传统生产过程中出现的大量有害的多酚损失，从而提供一种含有大量用于配制成品的原料中的可可多酚的产品。含可可多酚的配料是部分脱脂的可可固体。
• Synthetic methods for polyphenols
  申请人：Mars, Incorporated

  公开号：US20020128493A1

  公开（公告）日：2002-09-12

  A process is disclosed for the production of polyphenol oligomers having n polyphenol monomeric units, n being an integer from 2-18. The process includes coupling of a protected polyphenol, having protected phenolic hydroxyl groups, with a C-4 functionalized polyphenol monomer. The protected polyphenol may be a protected polyphenol monomer or a protected polyphenol oligomer having 2-17 monomeric units. Advantageously, polyphenol monomeric units forming the polyphenol oligomers may be the same or different flavanoid compounds.

  本发明公开了一种生产具有 n 个多酚单体单元（n 为 2-18 之间的整数）的多酚低聚物的工艺。该工艺包括将具有受保护酚羟基的受保护多酚与 C-4 官能化多酚单体偶联。受保护的多酚可以是具有 2-17 个单体单元的受保护多酚单体或受保护多酚低聚物。有利的是，形成多酚低聚物的多酚单体单元可以是相同或不同的类黄酮化合物。
• Products containing polyphenol (s) and L-arginine to stimulate nitric oxide production
  申请人：Mars Incorporated

  公开号：US20030104075A1

  公开（公告）日：2003-06-05

  Foods and pharmaceuticals which contain cocoa and/or nut procyanidin(s) in combination with L-arginine are effective to induce a physiological increase in nitric oxide production in a mammal having ingested the product. A preferred food product is a confection, particularly a dark or milk chocolate containing nuts. The procyanidins may be natural or synthetic and may be provided by food ingredients such as chocolate liquor and/or cocoa solids prepared from underfermented beans and nut skins. The L-arginine may be natural or synthetic and may be provided by food ingredients such as nut meats, nut pastes, and/or nut flours, seeds, seed pastes, and/or seed flours, or gelatin. The beneficial health effects may include, for example, reduced blood pressure, resistance to cardiovascular disease, and anticancer activity.

  含有可可和/或坚果原花青素以及 L-精氨酸的食品和药品能有效地诱导摄入该产品的哺乳动物体内一氧化氮的生理性增加。首选的食品是糖果，特别是含有坚果的黑巧克力或牛奶巧克力。原花青素可以是天然的，也可以是人工合成的，可以由食品配料提供，如巧克力液和/或由发酵不足的豆类和坚果皮制备的可可固体。L-精氨酸可以是天然的或合成的，可以由坚果肉、坚果糊和/或坚果粉、种子、种子糊和/或种子粉或明胶等食品配料提供。有益健康的效果可包括降低血压、抵抗心血管疾病和抗癌活性等。
• Synthesis of 4alpha-arylepicatechins
  申请人：Mars Incorporated

  公开号：US20030100775A1

  公开（公告）日：2003-05-29

  Oligomeric procyanidins containing 4&agr;-linked epicatechin units are rare in nature and have hitherto not been accessible through stereoselective synthesis. Provided herein is the preparation of the prototypical dimer, epicatechin-4&agr;,8-epicatechin, by reaction of the protected 4-ketones with aryllithium reagents derived by halogen/metal exchange from the aryl bromides. Removal of the 4-hydroxyl group from the resulting tertiary benzylic alcohols is effected by tri-n-butyltin hydride and trifluoroacetic acid in a completely stereoselective manner, resulting in hydride delivery exclusively from the &bgr; face.

  含有 4&agr;-连接表儿茶素单元的低聚原花青素在自然界中非常罕见，迄今为止还无法通过立体选择性合成获得。本文提供了一种制备原型二聚体表儿茶素-4&agr;,8-表儿茶素的方法，该方法是将受保护的 4-酮与通过卤素/金属交换从芳基溴化物中得到的芳基锂试剂进行反应。氢化三正丁基锡和三氟乙酸以完全立体选择性的方式从生成的叔苄醇中去除 4-羟基，结果氢化物完全从&bgr;面传递。