arucadiol | 105037-85-2

• 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: arucadiol
• 英文别名: miltiodiol；5,6-dihydroxy-1,1-dimethyl-7-propan-2-yl-2,3-dihydrophenanthren-4-one
• CAS: 105037-85-2
• 化学式: C₁₉H₂₂O₃
• 分子量: 298.382
• InChiKey: CEIJAQIIDANFLF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  次丹参醌 在 油酸甲酯 、 rose bengal 作用下， 反应 1560.0h， 生成 arucadiol
  参考文献：
  名称：

  迷迭香中的抗氧化剂rosmariquinone的供氢机理

  摘要：

  AbstractRosmariquinone (RQ), an ortho‐quinone diterpenoid found in rosemary, was shown to act as a hydrogen‐donating antioxidant. The proposed mechanism is based on the isolation of the catechol intermediate arucadiol (AD) in methyl oleate test systems. AD was also observed in a bulk soybean oil oxidation experiment, which supports the observation that RQ is converted to AD during oxidation of the oil. Because AD was found in both light‐induced oxidation and autoxidation test systems, the antioxidant mechanism proceeds in a similar manner. The antioxidant activities of RQ and AD were not significantly different in the autoxidation experiments, while AD was a significantly better (P<0.05) antioxidant than RQ in the light‐induced oxidation.

  DOI：

  10.1007/s11746-998-0127-3

文献信息

• Total Synthesis of 1-Oxomiltirone and Arucadiol
  作者：Chang Ho Oh、Chaehyeon Seong、Juyeon Kang、Uiseong Chai、Dinh Hung Mac

  DOI：10.1055/s-0039-1690743

  日期：2020.12

  A practical and efficient approach for the total synthesis of arucadiol and 1-oxomiltirone is reported. The key step which involves an intramolecular [4+2] cycloaddition catalyzed by gold(III) bromide or copper(II) triflate leads to the formation of 6-6-6-fused aromatic abietane core.

  报道了一种合成arucadiol和1-oxomiltirone的实用高效方法。其中关键步骤涉及由金(III)溴化物或铜(II)三氟乙酸盐催化的分子内[4+2]环加成，导致形成6-6-6融合芳香松节烷核。
• Use of Conjugated Dienones in Cyclialkylations:  Total Syntheses of Arucadiol, 1,2-Didehydromiltirone, (±)-Hinokione, (±)-Nimbidiol, Sageone, and Miltirone
  作者：George Majetich、Shuang Liu、Jing Fang、David Siesel、Yong Zhang

  DOI：10.1021/jo970570q

  日期：1997.10.1

  Functionalized hydrophenanthrenes can be prepared using a cyclialkylation-based strategy. These annulations are highly dependent on the directing effects of the arene substitutents and on conformational considerations. The utility of this methodology was featured in the syntheses of six diterpenoids.
• Hydrogen-donating mechanism of rosmariquinone, an antioxidant found in rosemary
  作者：Clifford A. Hall、Susan L. Cuppett、Pat Dussault

  DOI：10.1007/s11746-998-0127-3

  日期：1998.9

  AbstractRosmariquinone (RQ), an ortho‐quinone diterpenoid found in rosemary, was shown to act as a hydrogen‐donating antioxidant. The proposed mechanism is based on the isolation of the catechol intermediate arucadiol (AD) in methyl oleate test systems. AD was also observed in a bulk soybean oil oxidation experiment, which supports the observation that RQ is converted to AD during oxidation of the oil. Because AD was found in both light‐induced oxidation and autoxidation test systems, the antioxidant mechanism proceeds in a similar manner. The antioxidant activities of RQ and AD were not significantly different in the autoxidation experiments, while AD was a significantly better (P<0.05) antioxidant than RQ in the light‐induced oxidation.