(E)-1-(4'-hydroxy-3'-methoxyphenyl)-4-hexadecen-3-one

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: (E)-1-(4'-hydroxy-3'-methoxyphenyl)-4-hexadecen-3-one
• 英文别名: [12]-shogaol；(E)-1-(4-Hydroxy-3-methoxyphenyl)hexadec-4-en-3-one
• 化学式: C₂₃H₃₆O₃
• 分子量: 360.537
• InChiKey: WCQFXNQALHURHS-BUHFOSPRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  26
• 可旋转键数：
  15
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  姜酮 在 4-甲基苯磺酸吡啶 、 对甲苯磺酸 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 二氯甲烷 、 苯 为溶剂， 反应 2.0h， 生成 (E)-1-(4'-hydroxy-3'-methoxyphenyl)-4-hexadecen-3-one
  参考文献：
  名称：

  Side-chain length is important for shogaols in protecting neuronal cells from β-amyloid insult

  摘要：

  Ten shogaols were synthesized to evaluate the importance of the side-chain length in protecting cells from betaA(1-42) insult using PC12 rat pheochromocytoma and IMR-32 human neuroblastoma cells. The compounds cell protectivity against betaA insult was demonstrated using 3-[4,5-dimethylthiazol-2-yl]-2,5-diphenyltetrazolium bromide (MTT) reduction assay. The efficacy of cell protection from betaA insult by these shogaols was shown to improve as the length of the side chain increase. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.12.041

文献信息

• Influence of side chain structure changes on antioxidant potency of the [6]-gingerol related compounds
  作者：Dong-Liang Lu、Xiu-Zhuang Li、Fang Dai、Yan-Fei Kang、Yan Li、Meng-Meng Ma、Xiao-Rong Ren、Gao-Wei Du、Xiao-Ling Jin、Bo Zhou

  DOI：10.1016/j.foodchem.2014.05.077

  日期：2014.12

  structure determinants for antioxidant activity, we synthesized eight compounds differentiated by their side chains which are characteristic of the C1–C2 double bond, the C4–C5 double bond or the 5-OH, and the six- or twelve-carbon unbranched alkyl chain. Our results show that their antioxidant activity depends significantly on the side chain structure, the reaction mediums and substrates. Noticeably, existence

  [6]-生姜醇和[6]-生姜醇是姜中的主要刺激性成分，具有多种生物活性，包括抗氧化活性。为了探索其抗氧化活性的结构决定因素，我们合成了八种按侧链区分的化合物，这些侧链具有C 1 -C 2双键，C 4 -C 5的特征。双键或5-OH，以及六或十二个碳的直链烷基链。我们的结果表明，它们的抗氧化活性在很大程度上取决于侧链结构，反应介质和底物。值得注意的是，5-OH的存在会降低其形式氢转移和给电子的能力，但会增加其DNA损伤和脂质过氧化保护能力。此外，尽管显着降低了其DNA链断裂抑制活性，但链长从6个碳原子延长至12个碳原子仍增强了其抗溶血活性。
• Side-chain length is important for shogaols in protecting neuronal cells from β-amyloid insult
  作者：Darrick S.H.L Kim、Jin Yung Kim

  DOI：10.1016/j.bmcl.2003.12.041

  日期：2004.3

  Ten shogaols were synthesized to evaluate the importance of the side-chain length in protecting cells from betaA(1-42) insult using PC12 rat pheochromocytoma and IMR-32 human neuroblastoma cells. The compounds cell protectivity against betaA insult was demonstrated using 3-[4,5-dimethylthiazol-2-yl]-2,5-diphenyltetrazolium bromide (MTT) reduction assay. The efficacy of cell protection from betaA insult by these shogaols was shown to improve as the length of the side chain increase. (C) 2003 Elsevier Ltd. All rights reserved.