5-S-lipoylhydroxytyrosol | 1417424-30-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 5-S-lipoylhydroxytyrosol
• 英文别名: 8-[2,3-Dihydroxy-5-(2-hydroxyethyl)phenyl]sulfanyl-6-sulfanyloctanoic acid；8-[2,3-dihydroxy-5-(2-hydroxyethyl)phenyl]sulfanyl-6-sulfanyloctanoic acid
• CAS: 1417424-30-6
• 化学式: C₁₆H₂₄O₅S₂
• 分子量: 360.496
• InChiKey: WROQVOCJUOBOQW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  23
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  124
• 氢给体数：
  5
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  5-S-lipoylhydroxytyrosol 以 甲醇 、 aq. phosphate buffer 为溶剂， 反应 60.0h， 以10%的产率得到6-[[7-Carboxy-1-[2,3-dihydroxy-5-(2-hydroxyethyl)phenyl]sulfanylheptan-3-yl]disulfanyl]-8-[2,3-dihydroxy-5-(2-hydroxyethyl)phenyl]sulfanyloctanoic acid
  参考文献：
  名称：

  Synthesis and Bioactivity Profile of 5-S-Lipoylhydroxytyrosol-Based Multidefense Antioxidants with a Sizeable (Poly)sulfide Chain

  摘要：

  Novel polyfunctionalized antioxidants, 5-S-lipoylhydroxytyrosol (1) and its disulfide 2, trisulfide 3, and tetrasulfide 4, were prepared from tyrosol and dihydrolipoic acid in the presence, when appropriate, of sulfur. Compound 1 exhibited significant activity in the ferric reducing/antioxidant power (FRAP) assay (1.60 Trolox equiv), whereas polysulfides 2-4 were more efficient in the DPPH reduction assay (88-93% reduction vs 68% by Trolox). At 10 mu M concentration, all compounds 1-4 proved to be efficient hydroxyl radical scavengers (56-69% inhibition) in a Fenton reaction assay. When administered to human HepG2 cells, 1-4 proved to be nontoxic and exhibited marked protective effects against reactive oxygen species (ROS) generation (60-84% inhibition at 1 mu M concentration) and cell damage induced by 400 mu M tert-butylhydroperoxide. All compounds 1-4 exhibited overall greater antioxidant activity than hydroxytyrosol.

  DOI：

  10.1021/jf302690c
• 作为产物：
  描述：

  对羟基苯乙醇 在 2-碘酰基苯甲酸 作用下， 以 甲醇 为溶剂， 反应 1.25h， 生成 5-S-lipoylhydroxytyrosol
  参考文献：
  名称：

  Synthesis and Bioactivity Profile of 5-S-Lipoylhydroxytyrosol-Based Multidefense Antioxidants with a Sizeable (Poly)sulfide Chain

  摘要：

  Novel polyfunctionalized antioxidants, 5-S-lipoylhydroxytyrosol (1) and its disulfide 2, trisulfide 3, and tetrasulfide 4, were prepared from tyrosol and dihydrolipoic acid in the presence, when appropriate, of sulfur. Compound 1 exhibited significant activity in the ferric reducing/antioxidant power (FRAP) assay (1.60 Trolox equiv), whereas polysulfides 2-4 were more efficient in the DPPH reduction assay (88-93% reduction vs 68% by Trolox). At 10 mu M concentration, all compounds 1-4 proved to be efficient hydroxyl radical scavengers (56-69% inhibition) in a Fenton reaction assay. When administered to human HepG2 cells, 1-4 proved to be nontoxic and exhibited marked protective effects against reactive oxygen species (ROS) generation (60-84% inhibition at 1 mu M concentration) and cell damage induced by 400 mu M tert-butylhydroperoxide. All compounds 1-4 exhibited overall greater antioxidant activity than hydroxytyrosol.

  DOI：

  10.1021/jf302690c

文献信息

• Synthesis and Bioactivity Profile of 5-<i>S</i>-Lipoylhydroxytyrosol-Based Multidefense Antioxidants with a Sizeable (Poly)sulfide Chain
  作者：Lucia Panzella、Luisella Verotta、Luis Goya、Sonia Ramos、María Angeles Martín、Laura Bravo、Alessandra Napolitano、Marco d’Ischia

  DOI：10.1021/jf302690c

  日期：2013.2.27

  Novel polyfunctionalized antioxidants, 5-S-lipoylhydroxytyrosol (1) and its disulfide 2, trisulfide 3, and tetrasulfide 4, were prepared from tyrosol and dihydrolipoic acid in the presence, when appropriate, of sulfur. Compound 1 exhibited significant activity in the ferric reducing/antioxidant power (FRAP) assay (1.60 Trolox equiv), whereas polysulfides 2-4 were more efficient in the DPPH reduction assay (88-93% reduction vs 68% by Trolox). At 10 mu M concentration, all compounds 1-4 proved to be efficient hydroxyl radical scavengers (56-69% inhibition) in a Fenton reaction assay. When administered to human HepG2 cells, 1-4 proved to be nontoxic and exhibited marked protective effects against reactive oxygen species (ROS) generation (60-84% inhibition at 1 mu M concentration) and cell damage induced by 400 mu M tert-butylhydroperoxide. All compounds 1-4 exhibited overall greater antioxidant activity than hydroxytyrosol.