flavan-3, 4-diol | 5023-02-9

• 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: flavan-3, 4-diol
• 英文别名: 3,4-Dihydro-2-phenyl-2H-1-benzopyran-3,4-diol；2-phenyl-3,4-dihydro-2H-chromene-3,4-diol
• CAS: 5023-02-9
• 化学式: C₁₅H₁₄O₃
• 分子量: 242.274
• InChiKey: XIMADJWJJOMVID-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  18
• 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：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

文献信息

• [EN] METHOD FOR THE PREPARATION OF C-4 COUPLED FLAVONOIDS, PROANTHOCYANIDINS AND ANALOGUES THEREOF<br/>[FR] PROCÉDÉ DE PRÉPARATION DE FLAVONOÏDES COUPLÉS EN C-4, DE PROANTHOCYANIDINES ET D'ANALOGUES CORRESPONDANTS
  申请人：UNIV FREE STATE ZA

  公开号：WO2009147645A1

  公开（公告）日：2009-12-10

  The invention relates to a novel process for the preparation of C-4 coupled flavonoids, proanthocyanidins and analogues thereof. According to a specific application of the invention, there is provided a method for the preparation of proanthocyanidins and proanthocyanidin analogues.

  这项发明涉及一种新型的制备C-4偶联类黄酮、原花青素及其类似物的方法。根据该发明的一个具体应用，提供了一种制备原花青素和原花青素类似物的方法。
• GLUCOSYRINGIC ACID ANALOGS AS SWEETNESS PROFILE MODIFIERS
  申请人：PepsiCo, Inc.

  公开号：US20180020708A1

  公开（公告）日：2018-01-25

  The present disclosure provides novel sweetener compositions comprising a compound having a structure according to Formula I: wherein R 1 , R 2 , R 3 , and R 4 are described herein. Also provided are methods of modulating sweetness profile of a product by adding a compound of Formula I to the product, such as a beverage product or a food product. For example, the compound described herein can be added to increase the overall sweetness of a nutritive sweetener sweetened beverages; decrease the sweetness time-of-onset for high potency sweeteners such as rebaudioside A; decreasing bitter, metallic and licorice off-notes of high potency sweeteners; and improve the sweet quality of sweetened products.

  本公开提供了包含具有如下式I的结构的化合物的新型甜味剂组合物： 其中R1、R2、R3和R4如本文所述。还提供了通过向产品添加式I的化合物来调节产品的甜味特性的方法，例如饮料产品或食品产品。例如，本文描述的化合物可添加以增加富含甜味剂的饮料的整体甜度；减少高效甜味剂（如甜菊糖A）的甜味起始时间；减少高效甜味剂的苦味、金属味和甘草味等异味；并改善甜味产品的甜味质量。
• Flavonoids as Synergists for Enhancing the Action of Self-Tanning Substances
  申请人：Rudolph Thomas

  公开号：US20080279793A1

  公开（公告）日：2008-11-13

  The invention relates to the use of at least one flavonoid having an uncharged flavan skeleton as synergist for enhancing the action of self-tanning substances, such as trioses and tetroses, in cosmetic and dermatological formulations and to corresponding novel compositions and to the preparation thereof.

  这项发明涉及在化妆品和皮肤科制剂中使用至少一种具有未带电的黄酮骨架的黄酮类物质作为协同剂，以增强自日晒剂（如三糖和四糖）的作用，并涉及相应的新型组合物及其制备方法。
• USE OF FLAVONOIDS
  申请人：Rudolph Thomas

  公开号：US20090317342A1

  公开（公告）日：2009-12-24

  The present invention relates to the use of at least one flavonoid for odour improvement and/or odour stabilisation, and to corresponding compositions and the preparation thereof.

  本发明涉及至少一种黄酮类化合物用于改善气味和/或稳定气味，以及相应的组合物及其制备方法。
• [EN] SYNTHESIS OF C-3 COUPLED BIFLAVONOIDS AND C-3 COUPLED BIFLAVONOID ANALOGUES<br/>[FR] SYNTHÈSE DE BIFLAVONOÏDES COUPLÉS EN C-3 ET D'ANALOGUES DE BIFLAVONOÏDES COUPLÉS EN C-3
  申请人：UNIV FREE STATE ZA

  公开号：WO2011021167A1

  公开（公告）日：2011-02-24

  The invention relates to methods for the preparation of an optically inactive and optically active compounds which are selected from the group consisting of C-3 coupled biflavonoids and C-3 coupled biflavonoid analogues from a starting material or intermediate which are respectively selected from the group consisting of optically inactive or optically active flavan-3-ols and optically active flavan-3-ones, the method comprising the steps of (a) providing an optically inactive or active compound having a fIavan-3-ol structure or a compound which is a flavan-3-one, (b) if a compound having a flavan-3-ol structure with a hydroxy group on the C-3 carbon is selected as starting material, converting the hydroxy group on the C-3 carbon of the compound having the flavan-3-ol structure to an oxo group to form a flavan-3-one of that compound, (c) providing a compound having a nucleophilic aromatic moiety, which compound is selected from the group of compounds having a nucleophilic aromatic moiety and which have flavonoid base structures and compounds having a nucleophilic aromatic moiety and which do not have a flavonoid base structure, (d) contacting the flavan-3-one provided by step (a) or obtained by step (b) with the compound containing the nucleophilic aromatic moiety in the presence of a Lewis acid; (e) forming a first intermediate compound wherein the oxo group on the C-3 carbon is converted to a hydroxy group by virtue of nucleophilic addition when the compound containing the nucleophilic aromatic moiety is contacted to the C-3 carbon of the flavan-3-one, (f) subjecting the first intermediate compound to dehydration so as to introduce a double bond between the C-3 carbon and C-4 carbon of the intermediate compound with the concomitant removal of the hydroxy group from the C-3 carbon to form an optically active flavene compound which is substituted by the nucleophilic aromatic moiety on the C-3 carbon, (g) optionally subjecting the resultant flavene compound to hydroboration-oxidation hydration thereby removing said double bond between the C-3 carbon and the C-4 carbon with the concomitant introduction of a hydroxy group at the C-4 carbon to form a second intermediate compound, (h) further optionally oxidizing the second intermediate compound of step (g) thereby converting the hydroxy group at the said C-4 carbon to an oxo group, thereby forming a biflavonoid or biflavonoid analogue which is substituted by the selected nucleophilic aromatic moiety on the C-3 carbon, (ι) further optionally, and alternatively to step (h), subjecting the resultant flavene compound of step (f) to OsC4 dihydroxylation thereby removing said double bond between the C-3 carbon and C-4 carbon with the concomitant introduction of a hydroxy group at the C-4 carbon and a hydroxy group at the C-3 carbon to form a third intermediate compound, and (j) subjecting the third intermediate compound to dehydration whereby the hydroxy group at the C-3 carbon is removed and a double bond is introduced between the C-3 carbon and C-4 carbon thereby forming an enol product and allowing such enol product to rearrange spontaneously to form a biflavonoid or biflavonoid analogue having an oxo group at its C-4 carbon and which is substituted by the selected nucleophilic aromatic moiety on its C-3 carbon.

  该发明涉及从起始物质或中间体中选择的光学不活性和光学活性化合物的制备方法，所述化合物选自C-3偶联的双黄酮类和C-3偶联的双黄酮类类似物，所述起始物质或中间体分别选自光学不活性或光学活性的黄酮-3-醇和光学活性的黄酮-3-酮，所述方法包括以下步骤：(a)提供具有黄酮-3-醇结构或为黄酮-3-酮的化合物，该化合物是光学不活性或活性的；(b)如果选择具有C-3碳上羟基的黄酮-3-醇结构的化合物作为起始物质，则将该具有黄酮-3-醇结构的化合物上的C-3碳上的羟基转化为醛基，形成该化合物的黄酮-3-酮；(c)提供具有亲核芳香基团的化合物，所述化合物选自具有亲核芳香基团的化合物和具有黄酮基本结构的化合物以及具有亲核芳香基团的化合物和不具有黄酮基本结构的化合物；(d)在存在Lewis酸的情况下，将步骤(a)提供的或步骤(b)获得的黄酮-3-酮与含有亲核芳香基团的化合物接触；(e)形成第一中间化合物，其中通过亲核加成使含有亲核芳香基团的化合物与黄酮-3-酮的C-3碳接触时，C-3碳上的醛基转化为羟基；(f)将第一中间化合物脱水，以在中间化合物的C-3碳和C-4碳之间引入双键，并同时去除C-3碳上的羟基，形成一种在C-3碳上由亲核芳香基团取代的光学活性黄烯化合物；(g)可选地将所得的黄烯化合物经过氢硼氧化水合反应，从而去除C-3碳和C-4碳之间的双键，并同时在C-4碳引入羟基，形成第二中间化合物；(h)可选地进一步氧化步骤(g)中的第二中间化合物，从而将C-4碳上的羟基转化为醛基，形成在C-3碳上由选定的亲核芳香基团取代的双黄酮或双黄酮类似物；(ι)可选地，作为步骤(h)的替代，将步骤(f)中的所得黄烯化合物经过OsC4双羟基化反应，从而去除C-3碳和C-4碳之间的双键，并同时在C-4碳和C-3碳引入羟基，形成第三中间化合物；(j)将第三中间化合物脱水，从而去除C-3碳上的羟基，并在C-3碳和C-4碳之间引入双键，形成烯醇产物，并使该烯醇产物自发重排，形成在其C-4碳上具有醛基且在其C-3碳上由选定的亲核芳香基团取代的双黄酮或双黄酮类似物。