4',7-di-O-benzyl-kaempferol | 30652-27-8

• 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: 4',7-di-O-benzyl-kaempferol
• 英文别名: 4',7-di-O-benzylkaempferol；7,4'-O-dibenzyl kaempferol；7,4'-di-O-benzylkaempferol；7-benzyloxy-2-(4-benzyloxy-phenyl)-3,5-dihydroxy-chromen-4-one；4,7'-Di-O-benzylkaempferol；7,4'-Dibenzylkaempferol；3,5-Dihydroxy-7-phenylmethoxy-2-(4-phenylmethoxyphenyl)chromen-4-one
• CAS: 30652-27-8
• 化学式: C₂₉H₂₂O₆
• 分子量: 466.49
• InChiKey: DONNDJBIKGUZDG-UHFFFAOYSA-N

物化性质

• 沸点：
  693.2±55.0 °C(Predicted)
• 密度：
  1.363±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  35
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  85.2
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4',7-di-O-benzyl-kaempferol 在 甲醇 、 氢气 、 sodium methylate 、 palladium(II) hydroxide 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 生成 紫云英苷
  参考文献：
  名称：

  Study of Kaempferol Glycoside as an Insulin Mimic Reveals Glycon To Be the Key Active Structure

  摘要：

  Diabetes mellitus is increasing in prevalence with patient numbers rising throughout the world. Current treatments for-diabetes mellitus focus on control of blood glucose levels. Certain kinds of flavonoids or their glycosides stimulate cells to improve glucose uptake and lower blood glucose levels. We synthesized kaempferol 3-O-neohesperidoside (1) a naturally occurring substance present in Cyathea phalerata Mart., reported to mimic the action of insulin. Synthetic 1 promoted glucose uptake in the cultured cell line, L6. Further studies to determine the core structure responsible for this activity using synthetic compounds revealed neohesperidose to be the primary pharmacophore. These findings support the use of certain saccharides as a potential novel treatment for diabetes mellitus by replacing or supporting insulin.

  DOI：

  10.1021/ml100171x
• 作为产物：
  描述：

  5,7-二-(苄氧基)-2-(4-(苄氧基)苯基)-3-羟基-4H-苯并吡喃-4-酮 在 溶剂黄146 作用下， 以 水 为溶剂， 以56%的产率得到4',7-di-O-benzyl-kaempferol
  参考文献：
  名称：

  Study of Kaempferol Glycoside as an Insulin Mimic Reveals Glycon To Be the Key Active Structure

  摘要：

  Diabetes mellitus is increasing in prevalence with patient numbers rising throughout the world. Current treatments for-diabetes mellitus focus on control of blood glucose levels. Certain kinds of flavonoids or their glycosides stimulate cells to improve glucose uptake and lower blood glucose levels. We synthesized kaempferol 3-O-neohesperidoside (1) a naturally occurring substance present in Cyathea phalerata Mart., reported to mimic the action of insulin. Synthetic 1 promoted glucose uptake in the cultured cell line, L6. Further studies to determine the core structure responsible for this activity using synthetic compounds revealed neohesperidose to be the primary pharmacophore. These findings support the use of certain saccharides as a potential novel treatment for diabetes mellitus by replacing or supporting insulin.

  DOI：

  10.1021/ml100171x

文献信息

• Synthesis of Kaempferol 3-<i>O</i>-(3′′,6′′-Di-<i>O</i>-<i>E</i>-<i>p</i>-coumaroyl)-β-<scp>d</scp>-glucopyranoside, Efficient Glycosylation of Flavonol 3-OH with Glycosyl <i>o</i>-Alkynylbenzoates as Donors
  作者：Weizhun Yang、Jiansong Sun、Wenxiang Lu、Yan Li、Lei Shan、Wei Han、Wei-Dong Zhang、Biao Yu

  DOI：10.1021/jo1014189

  日期：2010.10.15

  linkage with a glycosyl bromide under conventional PTC conditions. In the second approach, 5,7,4′-tri-O-benzyl-kaempferol was readily prepared from 2′,4′,6′-trihydroxyacetophenone and p-hydroxybenzoic acid, which was coupled with a glucopyranosyl o-hexynylbenzoate under the catalysis of a gold(I) complex to provide the desired 3-O-glycoside in excellent yield. A variety of the glycosyl o-hexanylbenzoates

  Kaempferol 3- O-（3'，6''- di - O - E - p-香豆酰基）-β- d-吡喃葡萄糖苷（1），一种苏格兰松树幼苗的最佳代谢产物，可保护深层组织免受伤害。 UV-B代表典型的酰化黄酮醇3- O-糖苷。该化合物是通过两种方法首次合成的。第一种方法从山ka酚开始，其特征在于在常规PTC条件下与糖基溴化物形成黄酮醇3- O-糖苷键。在第二种方法中，可以很容易地从2'，4'，6'-三羟基苯乙酮和p制备5,7,4'-三-O-苄基-山emp酚-羟基苯甲酸在金（I）络合物的催化下与葡糖吡喃糖基邻己炔基苯甲酸酯偶联，以优异的产率提供所需的3- O-糖苷。还证实了多种配备有2- O-苯甲酰基的糖基邻-己基苯甲酸酯是构建黄酮醇3- O-糖苷键的高效供体。
• Chromone complexes
  申请人：Carola Christophe

  公开号：US20070191305A1

  公开（公告）日：2007-08-16

  The invention relates to complexes of certain chromone derivatives, to compositions which comprise such derivatives, to corresponding processes for the preparation of the chromone derivatives or of compositions comprising same, and to the use thereof, in particular for the care, maintenance or improvement of the general state of the skin or hair.

  该发明涉及某些咖啡因衍生物的络合物，以及包含这些衍生物的组合物，以及用于制备咖啡因衍生物或包含它们的组合物的相应过程，并且用途包括特别用于护理、维护或改善皮肤或头发的整体状态。
• Structure Elucidation and Synthesis of Flavonol Acylglycosides. III.. The synthesis of tiliroside
  作者：Barbara Vermes、Vedanta Mohan Chari、Hildebert Wagner

  DOI：10.1002/hlca.19810640630

  日期：1981.9.23

  Naturally occurring kaempferol 3-O-β-D-(6″-O-coumaroyl)glucopyranoside (tiliroside) has been synthesized thereby confirming its structure. This is the first acylated flavonoid glycoside to be synthesized.

  已经合成了天然存在的山3-酚3 - O - β -D-（6″ -O-香豆酰基）吡喃葡萄糖苷（罗罗糖苷），从而确认了其结构。这是第一个要合成的酰化类黄酮糖苷。
• Flavonoid complexes with cyclodextrins
  申请人：Wirth Corinna

  公开号：US20070155695A1

  公开（公告）日：2007-07-05

  The invention relates to complexes of certain flavonoid derivatives, of the formula I compositions which comprise such derivatives, corresponding processes for the preparation of the flavonoid derivatives or of compositions comprising same, and the use thereof, in particular for the care, preservation or improvement of the general state of the skin or hair. Formula (1), in which Z 1 to Z 4 and Z 6 to Z 10 each, independently of one another, denote H, OH, CH 3 COO, alkoxy, hydroxyalkoxy, mono- or oligoglycoside radicals and where the alkoxy and hydroxyalkoxy groups may be branched and unbranched and can have 1 to 18 C atoms. Formula (II) denotes, Z 5 is a mono- or the oligoglycoside radical, where bonded to this glycoside radical, in each case via an —O— group, is at least one radical selected from certain benzo molecule.

  本发明涉及某些黄酮衍生物的复合物，具有I式的组成物，包括这些衍生物的制备方法或包含它们的组合物的制备方法，以及它们的用途，特别是用于皮肤或头发的护理、保护或改善。式（1）中，Z1至Z4和Z6至Z10各自独立地表示H、OH、CH3COO、烷氧基、羟基烷氧基、单糖或寡糖基团，其中烷氧基和羟基烷氧基基团可以是支链和直链的，并且可以具有1到18个C原子。式（II）表示，Z5是单糖或寡糖基团，其中通过每个—O—基团，与该糖基团结合的至少有一种来自某些苯并分子的基团。
• Nahrungsmittel oder Nahrungsergänzungsmittel enthaltend Flavonoid-Derivate
  申请人：Merck Patent GmbH

  公开号：EP1847182A2

  公开（公告）日：2007-10-24

  Es werden Nahrungsmittel oder Nahrungsergänzungsmittel beschrieben, die mit einem oder mehreren Flavonoid-Derivaten angereichert sind oder diese enthalten.

  所述食品或食品补充剂富含或含有一种或多种类黄酮衍生物。