2,5-dimethyl-6-phytylquinol | 98931-24-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 2,5-dimethyl-6-phytylquinol
• 英文别名: 2,5-dimethyl-3-[(E,7R,11R)-3,7,11,15-tetramethylhexadec-2-enyl]benzene-1,4-diol
• CAS: 98931-24-9
• 化学式: C₂₈H₄₈O₂
• 分子量: 416.688
• InChiKey: SSWSVDWOYPVOBJ-WGEODTKDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11
• 重原子数：
  30
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,5-dimethyl-6-phytylquinol 在 tocopherol cyclase from spheroplasts of Anabaena variabilis 作用下， 以 丙酮 为溶剂， 生成 Beta-生育酚
  参考文献：
  名称：

  The substrate specificity of tocopherol cyclase

  摘要：

  The substrate specificity of the enzyme tocopherol cyclase from the blue-green algae Anabaena variabilis (Cyanobacteria) was investigated with 11 substrate analogues revealing the significance of three major recognition sites: (i) the OH group at C(1) of the hydroquinone, (ii) the (E) configuration of the double bond, and (iii) the length of the lipophilic side chain. Experiments with two affinity matrices suggest that substrates approach the enzyme's active site with the hydrophobic tail. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0968-0896(96)00125-3
• 作为产物：
  描述：

  3,7,11,15-四甲基-2-十六碳烯-1-醇 、 2,5-dimethylhydroquinone 在 aluminum oxide 、 三氟化硼乙醚 作用下， 以 四氢呋喃 为溶剂， 反应 15.0h， 生成 2,5-dimethyl-6-phytylquinol
  参考文献：
  名称：

  2-Methyl-6-phytylquinol and 2,3-dimethyl-5-phytylquinol as precursors of tocopherol synthesis in spinach chloroplasts

  摘要：

  The incorporation of [Me(methyl)-14C] from SAM(S-adenosylmethionine)-[Me-14C] into precursors indicates the following sequence of tocopherol synthesis in spinach: 2-methyl-6-phytylquinol (6-phytyltoluquinol) (1a) .fwdarw. 2,3-dimethyl-5-phytylquinol (phytylplastoquinol) (2a) .fwdarw. .gamma.-tocopherol (5a) .fwdarw. .alpha.-tocopherol (6). 1a is particularly preferred to 2-methyl-5-phytylquinol (1b) and 2-methyl-3-phytylquinol (1c). 1a only forms 2a. 2a is converted to 6 via 5a and, to a lesser extent, 2,5-dimethyl-6-phylquinol (2b) to 6 via .beta.-tocopherol (5b). Trimethylphytylquinol (3) is not an intermediate in the formation of 6. All reactions are independent of light.

  DOI：

  10.1016/s0031-9422(00)81963-9

文献信息

• The substrate specificity of tocopherol cyclase
  作者：Achim Stocker、Heinz Fretz、Haroun Frick、August Rüttimann、Wolf-Dietrich Woggon

  DOI：10.1016/0968-0896(96)00125-3

  日期：1996.7

  The substrate specificity of the enzyme tocopherol cyclase from the blue-green algae Anabaena variabilis (Cyanobacteria) was investigated with 11 substrate analogues revealing the significance of three major recognition sites: (i) the OH group at C(1) of the hydroquinone, (ii) the (E) configuration of the double bond, and (iii) the length of the lipophilic side chain. Experiments with two affinity matrices suggest that substrates approach the enzyme's active site with the hydrophobic tail. Copyright (C) 1996 Elsevier Science Ltd
• 2-Methyl-6-phytylquinol and 2,3-dimethyl-5-phytylquinol as precursors of tocopherol synthesis in spinach chloroplasts
  作者：Jürgen Soll、Gernot Schultz

  DOI：10.1016/s0031-9422(00)81963-9

  日期：1980.1

  The incorporation of [Me(methyl)-14C] from SAM(S-adenosylmethionine)-[Me-14C] into precursors indicates the following sequence of tocopherol synthesis in spinach: 2-methyl-6-phytylquinol (6-phytyltoluquinol) (1a) .fwdarw. 2,3-dimethyl-5-phytylquinol (phytylplastoquinol) (2a) .fwdarw. .gamma.-tocopherol (5a) .fwdarw. .alpha.-tocopherol (6). 1a is particularly preferred to 2-methyl-5-phytylquinol (1b) and 2-methyl-3-phytylquinol (1c). 1a only forms 2a. 2a is converted to 6 via 5a and, to a lesser extent, 2,5-dimethyl-6-phylquinol (2b) to 6 via .beta.-tocopherol (5b). Trimethylphytylquinol (3) is not an intermediate in the formation of 6. All reactions are independent of light.