hexa-O-methylogossypetin | 7741-47-1

• 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: hexa-O-methylogossypetin
• 英文别名: 3,5,7,8-tetramethoxy-2-(3,4-dimethoxyphenyl)-4-benzopyrone；3′,4′,3,5,7,8-hexamethoxyflavone；3,3′,4′,5,7,8-hexamethoxyflavone；limocitrin 3,5,7,4'-tetramethyl ether；3,5,7,8,3',4'-hexamethoxyflavone；gossypetin hexamethyl ether；2-(3,4-dimethoxyphenyl)-3,5,7,8-tetramethoxychromen-4-one
• CAS: 7741-47-1
• 化学式: C₂₁H₂₂O₈
• 分子量: 402.401
• InChiKey: XBZIUXVIWRAJKB-UHFFFAOYSA-N

物化性质

• 熔点：
  170-172 °C
• 沸点：
  598.2±50.0 °C(Predicted)
• 密度：
  1.30±0.1 g/cm3(Predicted)
• 物理描述：
  Solid

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  81.7
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  hexa-O-methylogossypetin 在 盐酸 、 溶剂黄146 作用下， 反应 2.0h， 生成 4H-1-苯并吡喃-4-酮,2-(3,4-二甲氧苯基)-5-羟基-3,7,8-三甲氧基-
  参考文献：
  名称：

  Antiproliferative Activities of Citrus Flavonoids against Six Human Cancer Cell Lines

  摘要：

  Citrus fruits contain high concentrations of several classes of phenols, including numerous hydroxycinnamates, flavonoid glycosides, and polymethoxylated flavones. The latter group of compounds occurs without glycosidic linkages and has been shown to inhibit the proliferation of a number of cancer cell lines. This antiproliferative property was further demonstrated against additional human cancer cell lines, and the anti proliferative actions of a series of synthetic methoxylated flavones were also studied. Similar to the naturally occurring compounds, the synthetic compounds exhibited strong antiproliferative activities. In many cases the IC50 values occurred below 10 mum. Other hydroxylated flavone and flavanone aglycons also exhibited antiproliferative activities against the cancer cell lines, with the flavones showing greater activities than the flavanones. Glycosylation of these compounds removed their activity. The strong antiproliferative activities of the polymethoxylated flavones suggest that they may have use as anticancer agents in humans.

  DOI：

  10.1021/jf020121d
• 作为产物：
  描述：

  栎精-3,5,7,3,4-五甲醚 在 二甲基二环氧乙烷 、 三溴化硼 、 potassium carbonate 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 5.33h， 生成 hexa-O-methylogossypetin
  参考文献：
  名称：

  Regioselective hydroxylation of 2-hydroxychalcones by dimethyldioxirane towards polymethoxylated flavonoids

  摘要：

  The flavone nucleus is part of a large number of natural products and medicinal compounds. In this presentation the novel regioselective hydroxylation of hydroxyarenes with DMD is described. The results showed further that flavonoids with 5-hydroxy group were selectively oxyfunctionalized at the para-position C8 carbon atom by DMD. Finally, according to this methodology, the naturally occurring isosinensetin, tangeretin, sinensetin, nobiletin, natsudaidain, gardenin B, 3,3',4',5,6,7,8-heptamethoxyflavone, quercetin and its derivatives were synthesized. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.01.023

文献信息

• Antimicrobial flavonoids from Psiadia trinervia and their methylated and acetylated derivatives
  作者：Ying Wang、Matthias Hamburger、Joseph Gueho、Kurt Hostettmann

  DOI：10.1016/s0031-9422(00)97976-7

  日期：1989.1

  Abstract From a dichloromethane extract and a hydrolysed methanolic extract from the leaves of Psiadia trinervia, 13 3-methylated flavonols have been isolated. Their structures were established by the usual spectroscopic methods (UV, EIMS, 1H and 13C NMR). Ayanin, casticin, chrysosplenol-D and 5,7,4′-trihydroxy-3,8-dimethoxyfiavone were responsible for the antifungal activity found in the preliminary

  摘要 从三叶蕨叶的二氯甲烷提取物和水解甲醇提取物中分离出 13 种 3-甲基化黄酮醇。它们的结构是通过通常的光谱方法（UV、EIMS、1H 和 13C NMR）确定的。Ayanin、casticin、chrysosplenol-D 和 5,7,4'-三羟基-3,8-二甲氧基黄酮负责在初步筛选中发现的抗真菌活性。Chrysosplenol-D、isokaempferide、5,7,4'-三羟基-3,3'-二甲氧基黄酮和 5,7,4'-三羟基-3,8-二甲氧基黄酮显示出抗菌活性。通过全甲基化和选择性甲基化 C-5 处的游离羟基制备了 29 种衍生物。使用 C. cucumerinum 和 B. cereus 作为测试生物，通过生物自显影测定法测定分离物和衍生物的抗微生物活性。
• CONTROL OF FLAVOR CHARACTERISTICS OF AND INDICATOR OF FRESHNESS IN FRUIT JUICE
  申请人：Havekotte Margaret

  公开号：US20090175995A1

  公开（公告）日：2009-07-09

  Control of flavor characteristics of and fresh taste in fruit juice, particularly citrus fruit juice, and especially orange juice.

  水果汁的味道特征和新鲜口感的控制，特别是柑橘类水果汁，尤其是橙汁。
• Compositions and methods of treating, reducing and preventing cardiovascular diseases and disorders with polymethoxyflavones
  申请人：——

  公开号：US20040214882A1

  公开（公告）日：2004-10-28

  Compositions and methods for the treatment, reduction and/or prevention of cardiovascular diseases and disorders are described. Individuals at high risk for developing or having cardiovascular disease or disorder may be treated with an effective dose of a polymethoxyflavone including limocitrin derivatives, quercetin derivatives, naturally occurring polymethoxyflavones, tocotrienols, and mixtures of these compounds.

  本文描述了治疗、减少和/或预防心血管疾病和障碍的组合物和方法。高风险患有或可能发展心血管疾病或障碍的个体，可以接受有效剂量的多甲氧黄酮，包括柠檬黄素衍生物、槲皮素衍生物、天然多甲氧黄酮、生育三烯酚和这些化合物的混合物。
• A taste modifier and a method of modifying taste
  申请人：SAN-EI GEN F.F.I., INC.

  公开号：EP0605261A2

  公开（公告）日：1994-07-06

  The present invention provides a taste modifier comprising a flavone derivative as an active ingredient of the general formula (I) : wherein Ri, R3, R4, R6 and R8 are independently methoxy group or hydrogen atom, R2 and R7 are methoxy group, and R5 is methoxy group or hydroxy group and a method of modifying taste, comprising adding a taste-modifying effective amount of the flavone derivative (I) to a product used in a mouth or an orally ingestible product. According to the present invention, various factors associated with taste can be modified. It relates to the modification of taste of a product used in a mouth or orally ingestible product, for example, enhancing the sourness, reducing the saltiness, inhibiting the unpleasant lasting of sweetness, enhancing the refreshing flavor and its continuity, reducing the flavor associated with acetic acid, and enhancing the body, deliciousness and savor associated with the combination of these tastes.

  本发明提供了一种由黄酮衍生物作为通式 (I) 的活性成分组成的味道调节剂： 其中 Ri、R3、R4、R6 和 R8 独立地为甲氧基或氢原子，R2 和 R7 为甲氧基，R5 为甲氧基或羟基，以及一种改变味道的方法，包括向口腔中使用的产品或口服产品中添加改变味道有效量的黄酮衍生物 (I)。根据本发明，可以改变与味道有关的各种因素。本发明涉及口服或口服产品的口味改良，例如增强酸味、减少咸味、抑制甜味的不愉快持久性、增强清爽口味及其连续性、减少与醋酸相关的口味，以及增强与这些口味组合相关的体感、美味和可口性。
• Control of flavor characteristics of and indicator of freshness in fruit juice
  申请人：TROPICANA PRODUCTS, INC.

  公开号：EP2274991A2

  公开（公告）日：2011-01-19

  The flavor characteristics of and fresh taste in fruit juice, particularly citrus fruit juice, and especially orange juice, are controlled by using the determined ratio of isolimonin to limonin to determine the amount of heat stress that has been inflicted upon the juice.

  果汁（尤其是柑橘类果汁，特别是橙汁）的风味特点和新鲜口感，是通过测定隔离柠檬素和柠檬甙的比例来确定果汁所受的热应力大小来控制的。