7-ethyl-3-hydroxy-2-(3,4,5-trihydroxy-phenyl)-chromen-4-one | 649551-44-0

• 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: 7-ethyl-3-hydroxy-2-(3,4,5-trihydroxy-phenyl)-chromen-4-one
• 英文别名: 7-Ethyl-3-hydroxy-2-(3,4,5-trihydroxyphenyl)-4h-1-benzopyran-4-one；7-ethyl-3-hydroxy-2-(3,4,5-trihydroxyphenyl)chromen-4-one
• CAS: 649551-44-0
• 化学式: C₁₇H₁₄O₆
• 分子量: 314.295
• InChiKey: DKLDXUIAHRMKGO-UHFFFAOYSA-N

物化性质

• 沸点：
  592.9±50.0 °C(Predicted)
• 密度：
  1.553±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  107
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  3-乙基苯酚 在 氢氧化钾 、 sodium hydroxide 、 三氯化铝 、 双氧水 、 三溴化硼 、 三乙胺 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 254.25h， 生成 7-ethyl-3-hydroxy-2-(3,4,5-trihydroxy-phenyl)-chromen-4-one
  参考文献：
  名称：

  Potential therapeutic antioxidants that combine the radical scavenging ability of myricetin and the lipophilic chain of vitamin E to effectively inhibit microsomal lipid peroxidation

  摘要：

  The flavonol myricetin, reacts with oxygen-centred galvinoxyl radicals 28 times faster than d-alpha-tocopherol (vitamin E), the main lipid-soluble antioxidant in biological membranes. Moreover, each myricetin molecule reduces twice as many such radicals as vitamin E. However, myricetin fails to protect vitamin E-deficient microsomes from lipid peroxidation as assessed by the formation of thiobarbituric acid reactive substances (TBARS). Novel and potentially therapeutic antioxidants have been prepared that combine the radical-scavenging ability of a myricetin-like head group with a lipophilic chain similar to that of vitamin E. C-6-C-12 alkyl chains are attached to the A-ring of either a 3,3',4',5'-tetrahydroxyflavone or a 3,2',4',5'-tetrahydroxyflavone head group to give lipophilic flavonoids (Clog P = 4 to 10) that markedly inhibit iron-ADP catalysed oxidation of microsomal preparations. Orientation of the head group as well as total lipophilicity are important determinants of antioxidant efficacy. MM2 models indicate that our best straight chain 7-alkylflavonoids embed to the same depth in the membrane as vitamin E. The flavonoid head groups are prepared by aldol condensation followed by Algar-Flynn-Oyamada (AFO) oxidation or by Baker-Venkataraman re-arrangement. The alkyl tails are introduced by Suzuki or Negishi palladium-catalysed cross-coupling or by cross-metathesis catalysed by first generation Grubbs catalyst, which tolerate phenolic hydroxyl and ketone groups. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.02.031
• 作为试剂：
  描述：

  7-ethyl-3-hydroxy-2-(3,4,5-trimethoxy-phenyl)-chromen-4-one 、 三溴化硼 、 甲醇 、 水 在 7-ethyl-3-hydroxy-2-(3,4,5-trihydroxy-phenyl)-chromen-4-one 作用下， 以 二氯甲烷 为溶剂， 反应 42.0h， 生成 7-ethyl-3-hydroxy-2-(3,4,5-trihydroxy-phenyl)-chromen-4-one
  参考文献：
  名称：

  Flavonoid compounds as therapeutic antioxidants

  摘要：

  描述了具有抗氧化活性的新型黄酮类化合物。公式1。已经证明这些化合物在生物系统中表现出抗氧化性质，并描述了它们在防晒霜或护肤组合物中的实用性，或用于治疗涉及氧化损伤的疾病，特别是治疗阿尔茨海默病或缺血再灌注损伤的治疗或预防。

  公开号：

  US20060137207A1

文献信息

• [EN] FLAVONOID COMPOUNDS AS THERAPEUTIC ANTIOXIDANTS<br/>[FR] COMPOSES FLAVONOIDES EN TANT QU'ANTIOXYDANTS THERAPEUTIQUES
  申请人：ROWETT RES INST

  公开号：WO2004007475A1

  公开（公告）日：2004-01-22

  Novel flavonoid compounds having anti-oxidant activity are described. Formula (1). The compounds have been shown to exhibit anti-oxidative properties in biological systems and their utility in a sunscreen or skincare composition or to treat conditions involving oxidative damage, especially curative or prophylactic treatment of Alzheimer's disease or ischaemia-reperfusion and injury, is described.

  描述了具有抗氧化活性的新型黄酮类化合物。公式（1）。已经证明这些化合物在生物系统中展现出抗氧化特性，其在防晒霜或护肤品中的用途，或用于治疗涉及氧化损伤的情况，特别是治疗或预防治疗阿尔茨海默病或缺血再灌注和损伤的情况。
• COMPOUNDS
  申请人：Kong Thoo Lin Paul

  公开号：US20100151508A1

  公开（公告）日：2010-06-17

  Flavonoid-type compounds of the Formula (II); in which R 1 is alkyl C 2 to C 20 , R 2 , R 3 , R 4 and R 5 are any one or more of hydrogen, alkyl, alkenyl, alkynyl, phenyl or benzyl, especially 7-decyl-3-hydroxy-2-(3,4,5-trihydroxyphenyl)-4H-1-benzopy-ran-4-one or 7-ethyl-3-hydroxy-2-(3,4,5-trihydroxyphenyl)-4H-1-benzopyran-4-one provide fluorescent probes and antioxidants, and are useful in discriminating healthy and stressed cells.

  公式（II）中的黄酮类化合物;其中R1是烷基C2到C20，R2，R3，R4和R5是氢，烷基，烯基，炔基，苯基或苄基中的任何一个或多个，特别是7-癸基-3-羟基-2-（3,4,5-三羟基苯基）-4H-1-苯并吡喃-4-酮或7-乙基-3-羟基-2-（3,4,5-三羟基苯基）-4H-1-苯并吡喃-4-酮提供荧光探针和抗氧化剂，并且对于区分健康和受压力细胞非常有用。
• FLAVONOID COMPOUNDS AS THERAPEUTIC ANTIOXIDANTS
  申请人：The Rowett Research Institute

  公开号：EP1534698B1

  公开（公告）日：2007-09-19
• COMPOSITIONS FOR SLEEPING DISORDERS
  申请人：Chan Hsiao Chang

  公开号：US20090124627A1

  公开（公告）日：2009-05-14

  Provided herein is a method for treating, preventing, or ameliorating a disorder such as insomnia or another sleeping disorder using a composition that contains an effective amount of one or more compounds.
• US7601754B2
  申请人：——

  公开号：US7601754B2

  公开（公告）日：2009-10-13