1-(4'-decyl-2'-hydroxyphenyl)-2-methoxy-3-(2'',4'',5''-trimethoxyphenyl)propan-1,3-dione | 649551-94-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 1-(4'-decyl-2'-hydroxyphenyl)-2-methoxy-3-(2'',4'',5''-trimethoxyphenyl)propan-1,3-dione
• 英文别名: 1-(2'-hydroxy-4'-decylphenyl)-2-methoxy-3-(2'',4'',5''-trimethoxyphenyl)-propan-1,3-dione；1-(4-Decyl-2-hydroxyphenyl)-2-methoxy-3-(2,4,5-trimethoxyphenyl)propane-1,3-dione
• CAS: 649551-94-0
• 化学式: C₂₉H₄₀O₇
• 分子量: 500.632
• InChiKey: YDLPHQZZNHZAOQ-UHFFFAOYSA-N

物化性质

• 熔点：
  99-101 °C
• 沸点：
  647.6±55.0 °C(Predicted)
• 密度：
  1.099±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.3
• 重原子数：
  36
• 可旋转键数：
  17
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  91.3
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1-(4'-decyl-2'-hydroxyphenyl)-2-methoxy-3-(2'',4'',5''-trimethoxyphenyl)propan-1,3-dione 在 三氟甲磺酸三甲基硅酯 、 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 23.0h， 生成 7-decyl-3,2',4',5'-tetrahydroxy-flavone
  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
• 作为产物：
  描述：

  1-(2,4-二羟基苯基)-2-甲氧基-1-乙酮 在 2,6-二甲基吡啶 、 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 5.0h， 生成 1-(4'-decyl-2'-hydroxyphenyl)-2-methoxy-3-(2'',4'',5''-trimethoxyphenyl)propan-1,3-dione
  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

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。
• 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。
• US7601754B2
  申请人：——

  公开号：US7601754B2

  公开（公告）日：2009-10-13