3,6-dimethyl-2-methoxy-5-hydroxydecyl-p-benzo-quinone | 1270932-01-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 3,6-dimethyl-2-methoxy-5-hydroxydecyl-p-benzo-quinone
• 英文别名: 2-(10-Hydroxydecyl)-5-methoxy-3,6-dimethylcyclohexa-2,5-diene-1,4-dione
• CAS: 1270932-01-8
• 化学式: C₁₉H₃₀O₄
• 分子量: 322.445
• InChiKey: QVDQFOODKGSLRP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  23
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  11-羟基十一烷酸 、 2-methoxy-3,6-dimethyl-1,4-benzoquinone 在 silver nitrate 、 dipotassium peroxodisulfate 、 水 作用下， 以 乙腈 为溶剂， 以15%的产率得到3,6-dimethyl-2-methoxy-5-hydroxydecyl-p-benzo-quinone
  参考文献：
  名称：

  Synthesis and characterization of mitoQ and idebenone analogues as mediators of oxygen consumption in mitochondria

  摘要：

  Analogues of mitoQ and idebenone were synthesized to define the structural elements that support oxygen consumption in the mitochondrial respiratory chain. Eight analogues were prepared and fully characterized, then evaluated for their ability to support oxygen consumption in the mitochondrial respiratory chain. While oxygen consumption was strongly inhibited by mitoQ analogues 2-4 in a chain length-dependent manner, modification of idebenone by replacement of the quinone methoxy groups by methyl groups (analogues 6-8) reduced, but did not eliminate, oxygen consumption. Idebenone analogues 6-8 also displayed significant cytoprotective properties toward cultured mammalian cells in which glutathione had been depleted by treatment with diethyl maleate. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.06.104

文献信息

• Synthesis and characterization of mitoQ and idebenone analogues as mediators of oxygen consumption in mitochondria
  作者：Damien Y. Duveau、Pablo M. Arce、Robert A. Schoenfeld、Nidhi Raghav、Gino A. Cortopassi、Sidney M. Hecht

  DOI：10.1016/j.bmc.2010.06.104

  日期：2010.9

  Analogues of mitoQ and idebenone were synthesized to define the structural elements that support oxygen consumption in the mitochondrial respiratory chain. Eight analogues were prepared and fully characterized, then evaluated for their ability to support oxygen consumption in the mitochondrial respiratory chain. While oxygen consumption was strongly inhibited by mitoQ analogues 2-4 in a chain length-dependent manner, modification of idebenone by replacement of the quinone methoxy groups by methyl groups (analogues 6-8) reduced, but did not eliminate, oxygen consumption. Idebenone analogues 6-8 also displayed significant cytoprotective properties toward cultured mammalian cells in which glutathione had been depleted by treatment with diethyl maleate. (C) 2010 Elsevier Ltd. All rights reserved.