7-octyl-3-hydroxy-2-(3,4,5-trihydroxy-phenyl)-chromen-4-one | 649551-47-3

• 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-octyl-3-hydroxy-2-(3,4,5-trihydroxy-phenyl)-chromen-4-one
• 英文别名: 3-Hydroxy-7-octyl-2-(3,4,5-trihydroxyphenyl)-4H-1-benzopyran-4-one；3-hydroxy-7-octyl-2-(3,4,5-trihydroxyphenyl)chromen-4-one
• CAS: 649551-47-3
• 化学式: C₂₃H₂₆O₆
• 分子量: 398.456
• InChiKey: MXEBOWBDFCJVJP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  107
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 7-octyl-3-hydroxy-2-(3,4,5-trihydroxy-phenyl)-chromen-4-one 在 吡啶 、 4-二甲氨基吡啶 作用下， 生成 3-acetoxy-7-octyl-2-(3,4,5-triacetoxy-phenyl)-chromen-4-one
  参考文献：
  名称：

  [EN] FLAVONOID COMPOUNDS AS THERAPEUTIC ANTIOXIDANTS
  [FR] COMPOSES FLAVONOIDES EN TANT QU'ANTIOXYDANTS THERAPEUTIQUES

  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。

  公开号：

  WO2004007475A1
• 作为产物：
  描述：

  3-acetoxy-7-octyl-2-(3,4,5-triacetoxy-phenyl)-chromen-4-one 在 盐酸 、 甲醇 作用下， 反应 1.0h， 生成 7-octyl-3-hydroxy-2-(3,4,5-trihydroxy-phenyl)-chromen-4-one
  参考文献：
  名称：

  [EN] FLAVONOID COMPOUNDS AS THERAPEUTIC ANTIOXIDANTS
  [FR] COMPOSES FLAVONOIDES EN TANT QU'ANTIOXYDANTS THERAPEUTIQUES

  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。

  公开号：

  WO2004007475A1

文献信息

• Flavonoid compounds as therapeutic antioxidants
  申请人：Caldwell Thomas Stuart

  公开号：US20060137207A1

  公开（公告）日：2006-06-29

  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 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。
• Potential therapeutic antioxidants that combine the radical scavenging ability of myricetin and the lipophilic chain of vitamin E to effectively inhibit microsomal lipid peroxidation
  作者：Christopher J. Bennett、Stuart T. Caldwell、Donald B. McPhail、Philip C. Morrice、Garry G. Duthie、Richard C. Hartley

  DOI：10.1016/j.bmc.2004.02.031

  日期：2004.5

  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.
• FLAVONOID COMPOUNDS AS THERAPEUTIC ANTIOXIDANTS
  申请人：The Rowett Research Institute

  公开号：EP1534698B1

  公开（公告）日：2007-09-19
• US7601754B2
  申请人：——

  公开号：US7601754B2

  公开（公告）日：2009-10-13