2,2,5,7,8-pentamethylchroman-6-yl benzoate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 2,2,5,7,8-pentamethylchroman-6-yl benzoate
• 英文别名: (2,2,5,7,8-Pentamethyl-3,4-dihydrochromen-6-yl) benzoate
• 化学式: C₂₁H₂₄O₃
• 分子量: 324.42
• InChiKey: MZRINSGUPZEJNQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3,4-二氢-2,2,5,7,8-五甲基-2H-1-苯并吡喃-6-酚 、 苯甲酰氯 生成 2,2,5,7,8-pentamethylchroman-6-yl benzoate
  参考文献：
  名称：

  Active oxygen chemistry within the liposomal bilayer

  摘要：

  We have previously shown that the location and orientation of compounds intercalated within the lipid bilayer can be qualitatively determined using an NMR chemical shift-polarity correlation. We describe herein the results of our application of this method to analogs of Vitamin E, ubiquinol and ubiquinone. The results indicate that tocopherol-and presumably the corresponding tocopheroxyl radical-reside adjacent to the interface, and can, therefore, abstract a hydrogen atom from ascorbic acid. On the other hand, the decaprenyl substituted ubiquinol and ubiquinone lie substantially deeper within the lipid membrane. Yet, contrary to the prevailing literature, their location is far from being the same. Ubiquinone-10 is situated above the long-chain fatty acid "slab". Ubiquinol-10 dwells well within the lipid slab, presumably out of "striking range" of Vitamin C. Nevertheless, ubiquinol can act as an antioxidant by reducing C- or O-centered lipid radicals or by recycling the lipid-resident tocopheroxyl radical. (C) 2004 Elsevier Ireland Ltd. All rights reserved.

  DOI：

  10.1016/j.chemphyslip.2004.04.007

文献信息

• Active oxygen chemistry within the liposomal bilayer
  作者：Michal Afri、Benjamin Ehrenberg、Yeshayahu Talmon、Judith Schmidt、Yael Cohen、Aryeh A. Frimer

  DOI：10.1016/j.chemphyslip.2004.04.007

  日期：2004.8

  We have previously shown that the location and orientation of compounds intercalated within the lipid bilayer can be qualitatively determined using an NMR chemical shift-polarity correlation. We describe herein the results of our application of this method to analogs of Vitamin E, ubiquinol and ubiquinone. The results indicate that tocopherol-and presumably the corresponding tocopheroxyl radical-reside adjacent to the interface, and can, therefore, abstract a hydrogen atom from ascorbic acid. On the other hand, the decaprenyl substituted ubiquinol and ubiquinone lie substantially deeper within the lipid membrane. Yet, contrary to the prevailing literature, their location is far from being the same. Ubiquinone-10 is situated above the long-chain fatty acid "slab". Ubiquinol-10 dwells well within the lipid slab, presumably out of "striking range" of Vitamin C. Nevertheless, ubiquinol can act as an antioxidant by reducing C- or O-centered lipid radicals or by recycling the lipid-resident tocopheroxyl radical. (C) 2004 Elsevier Ireland Ltd. All rights reserved.