fisetin dihydrate | 345909-34-4

• 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: fisetin dihydrate
• 英文别名: 2-(3,4-Dihydroxyphenyl)-3,7-dihydroxy-4H-chromen-4-one hydrate；2-(3,4-dihydroxyphenyl)-3,7-dihydroxychromen-4-one;hydrate
• CAS: 345909-34-4
• 化学式: C₁₅H₁₀O₆*2H₂O
• 分子量: 322.271
• InChiKey: GYHFUROKCOMWNQ-UHFFFAOYSA-N

物化性质

• 熔点：
  >330 °C (lit.)
• 稳定性/保质期：

  在常温常压下稳定，应避免与强氧化剂、强碱和水分直接接触。

计算性质

• 辛醇/水分配系数(LogP)：
  1.46
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  108
• 氢给体数：
  5
• 氢受体数：
  7

安全信息

• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

制备方法与用途

理化性质

漆黄素来源于漆树科植物木腊树 Rhus succedanea L. ，是一种黄色针状结晶，在稀乙醇中存在，熔点为3300°C（分解）。它几乎不溶于水，却能很好地溶解在乙醇中。

黄酮类化合物

漆黄素又称非瑟酮，是一种天然的黄酮类化合物。最早于1833年从漆树中分离提取得到，具有抗氧化、抗炎、抗肿瘤和抗衰老等多种生物活性作用。

临床评价

漆黄素（Fisetin, FIT）是从漆树科植物木腊树 Toxicodendron sylvestre (Sieb. et Zucc.) O. Kuntze 中提取的一种黄色针状结晶化合物，广泛存在于蔬菜和水果中。其独特的B环上邻二酚羟基结构赋予了漆黄素较强的药理作用，如抗病毒、治疗黄疽型病毒肝炎；抑制细胞凋亡、人黑色素瘤；抗血管增生、神经保护以及抗癌等。尽管漆黄素在预防和治疗疾病方面表现出显著效果，但由于其较低的水溶性（溶解度小于1 mg/mL）、化学不稳定性、脂溶性和低溶出率及较快的代谢速率等特点，限制了其药物制剂与临床应用的发展。

反应信息

• 作为反应物：
  描述：

  硫酸氧钒水合物 、 fisetin dihydrate 在 NaOH 、 H₂SO₄ 作用下， 以 H₂O 为溶剂， 生成 [VO(OH)(fisetin(-1H))]*3H2O
  参考文献：
  名称：

  黄酮衍生物作为潜在的胰岛素模拟剂的新型钒基配合物的热稳定性

  摘要：

  一系列新的VO（OH）L· n H 2 O类型的配合物（（1）L：非瑟汀，n  = 3；（2）L：槲皮素，n  = 2；（3）L：morin，n  = 4）合成并通过分析，红外和电子数据进行表征。红外光谱中证明的修饰与所有复合物中黄酮类化合物的双齿黄酮的存在有关。电子反射光谱显示d – d钒（IV）离子的方形-金字塔形立体化学的跃迁特性。合成气流中的热分析（TG，DTA）阐明了组成以及水分子的数量和性质。TG曲线显示三个完全分开的热事件。第一个对应于较低温度下的失水，其后是类黄酮衍生物的分解和较高温度下的热解。最终产物是钒氧化物。

  DOI：

  10.1007/s10973-009-0387-7

文献信息

• Neurogenic compounds
  申请人：Mars Incorporated

  公开号：EP2478901A2

  公开（公告）日：2012-07-25

  The invention relates to method(s) of use of the compound(s) described herein, e.g. method for stimulating neurogenesis, including in vitro neurogenesis, by contacting neuronal progenitor cells with an effective amount of the compound(s) described herein; method for treatment of a subject in need of treatment with a neurogenic compound; and/or for treatment of a disease or condition associated with damage to the hippocampus. The subject may be a human or a veterinary animal.

  本发明涉及本文所述化合物的使用方法，例如通过将神经元祖细胞与有效量的本文所述化合物接触来刺激神经发生（包括体外神经发生）的方法；用神经发生化合物治疗需要治疗的受试者的方法；和/或治疗与海马受损有关的疾病或病症的方法。受试者可以是人或兽医动物。
• RHUS VERNICIFLUA STOKES EXTRACT HAVING INCREASED CONTENT OF ACTIVE FLAVONOID COMPOUND AND METHOD FOR PREPARING SAME
  申请人：Azi. Co., Ltd

  公开号：EP2604274A1

  公开（公告）日：2013-06-19

  The present invention relates to Rhus verniciflua Stokes extract having an increased content of an active flavonoid compound through a gas bubbling treatment, a method for preparing the Rhus verniciflua Stokes extract, and a method for converting fustin into fisetin through the gas bubbling treatment of a solution containing fustin. The method for preparing the Rhus verniciflua Stokes extract of the present invention can convert the conventional Rhus verniciflua Stokes extract having high content of fustin and low content of fisetin into a Rhus verniciflua Stokes extract having high content of fisetin. Therefore, the Rhus verniciflua Stokes extract of the present invention can be commercialized into natural anticancer agents, anticancer and cancer prevention food products, and health functional foods due to the excellent bioactivity thereof, and promote the development of relevant industries through the high added-value of Rhus verniciflua Stokes. In addition, the method for converting fustin into fisetin can be applied to other natural substances and be used as a method for enhancing the functionality thereof by increasing the content of a high active flavonoid, thereby becoming an enabling technology that can lead high-functionalization of natural substances.

  本发明涉及通过气泡处理增加活性黄酮化合物含量的斯托克斯杜鹃花提取物、制备斯托克斯杜鹃花提取物的方法，以及通过气泡处理含杜鹃花素的溶液将杜鹃花素转化为鱼腥草素的方法。本发明的制备斯托克斯杜鹃花提取物的方法可以将传统的富士丁含量高、鱼腥草素含量低的斯托克斯杜鹃花提取物转化为鱼腥草素含量高的斯托克斯杜鹃花提取物。因此，本发明的紫竹提取物因其优异的生物活性，可商品化为天然抗癌剂、抗癌防癌食品和保健功能食品，并通过紫竹的高附加值促进相关产业的发展。此外，将 fustin 转化为 fisetin 的方法还可应用于其他天然物质，通过增加高活性黄酮类化合物的含量来增强其功能性，从而成为引领天然物质高功能化的赋能技术。
• NEUROGENIC COMPOUNDS
  申请人：Mars Incorporated

  公开号：EP2117306A2

  公开（公告）日：2009-11-18
• Methods and compositions for the treatment of neurodegenerative disorders
  申请人：Jin Xiaowei

  公开号：US20080044390A1

  公开（公告）日：2008-02-21

  The present invention features compositions, kits, and methods for treating, preventing, and ameliorating neurodegenerative disorders, e.g., Huntington's disease.
• Rhus Verniciflua Stokes Extract Having Increased Content Of Active Flavonoid Compound And Method For Preparing Same
  申请人：Park Sang-Jae

  公开号：US20120283322A1

  公开（公告）日：2012-11-08

  The present invention relates to Rhus verniciflua Stokes extract having an increased content of an active flavonoid compound through a gas bubbling treatment, a method for preparing the Rhus verniciflua Stokes extract, and a method for converting fustin into fisetin through the gas bubbling treatment of a solution containing fustin. The method for preparing the Rhus verniciflua Stokes extract of the present invention can convert the conventional Rhus verniciflua Stokes extract having high content of fustin and low content of fisetin into a Rhus verniciflua Stokes extract having high content of fisetin. Therefore, the Rhus verniciflua Stokes extract of the present invention can be commercialized into natural anticancer agents, anticancer and cancer prevention food products, and health functional foods due to the excellent bioactivity thereof, and promote the development of relevant industries through the high added-value of Rhus verniciflua Stokes. In addition, the method for converting fustin into fisetin can be applied to other natural substances and be used as a method for enhancing the functionality thereof by increasing the content of a high active flavonoid, thereby becoming an enabling technology that can lead high-functionalization of natural substances.