12,13-epoxyxanthorrhizol | 364373-61-5

• 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: 12,13-epoxyxanthorrhizol
• 英文别名: 5-[(2R)-4-(3,3-dimethyloxiran-2-yl)butan-2-yl]-2-methylphenol
• CAS: 364373-61-5
• 化学式: C₁₅H₂₂O₂
• 分子量: 234.338
• InChiKey: BQAQGBHVNVLESL-IAPIXIRKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  32.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (R)-5-(1,5-二甲基-4-己烯基)-邻甲酚 在 碳酸氢钠 、 间氯过氧苯甲酸 作用下， 以 氯仿 为溶剂， 反应 1.0h， 以50%的产率得到12,13-epoxyxanthorrhizol
  参考文献：
  名称：

  Ent-trachyloban-19-oic acid isolated from Iostephane heterophylla as a promising antibacterial agent against Streptococcus mutans biofilms

  摘要：

  From the roots of Iostephane heterophylla, six known compounds, namely, ent-trachyloban-19-oic acid (1), the mixture of ent-kaur-16-en-19-oic acid (2) and ent-beyer-15-en-19-oic acid (3), xanthorrhizol (4), 16 alpha-hydroxy-ent-kaurane (5) and 16 alpha-hydroxy-ent-kaur-11-en-19-oic acid (6) were isolated using a bioassay-guided fractionation method. The known compounds (1-6) were identified by comparison of their spectroscopic data with reported values in the literature. In an attempt to increase the resultant antimicrobial activity of 1 and 4, a series of reactions was performed on ent-trachyloban-19-oic acid (1) and xanthorrhizol (4), to obtain derivatives 1a, 1b, and 4a-4d. All the isolated compounds (1-6) and the derivatives 1a, 1b, and 4a-4d were evaluated for their antimicrobial activity against two oral pathogens, Streptococcus mutans and Porphyromonas gingivalis associated with caries and periodontal disease, respectively. Compounds 1, 1b, 2+3, 4 and 4d inhibited the growth of S. mutans with concentrations ranging from 4.1 mu g/mL to 70.5 mu g/mL No significant activity was found on P. gingivalis except for 4 with an MIC of 6.8 mu g/mL The ability of 1, 1b, 2+3, 4 and 4d to inhibit biofilm formation by S. mutans was evaluated. It was found that 1, 1b, 4 and 4d interfered with the establishment of S. mutans biofilms, inhibiting their development at 32.5, 125.0, 14.1 and 24.4 mu g/mL, respectively. (C) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.fitote.2011.12.022

文献信息

• Ent-trachyloban-19-oic acid isolated from Iostephane heterophylla as a promising antibacterial agent against Streptococcus mutans biofilms
  作者：Dulce M. Hernández、Gloria Díaz-Ruiz、Blanca E. Rivero-Cruz、Robert A. Bye、María Isabel Aguilar、J. Fausto Rivero-Cruz

  DOI：10.1016/j.fitote.2011.12.022

  日期：2012.4

  From the roots of Iostephane heterophylla, six known compounds, namely, ent-trachyloban-19-oic acid (1), the mixture of ent-kaur-16-en-19-oic acid (2) and ent-beyer-15-en-19-oic acid (3), xanthorrhizol (4), 16 alpha-hydroxy-ent-kaurane (5) and 16 alpha-hydroxy-ent-kaur-11-en-19-oic acid (6) were isolated using a bioassay-guided fractionation method. The known compounds (1-6) were identified by comparison of their spectroscopic data with reported values in the literature. In an attempt to increase the resultant antimicrobial activity of 1 and 4, a series of reactions was performed on ent-trachyloban-19-oic acid (1) and xanthorrhizol (4), to obtain derivatives 1a, 1b, and 4a-4d. All the isolated compounds (1-6) and the derivatives 1a, 1b, and 4a-4d were evaluated for their antimicrobial activity against two oral pathogens, Streptococcus mutans and Porphyromonas gingivalis associated with caries and periodontal disease, respectively. Compounds 1, 1b, 2+3, 4 and 4d inhibited the growth of S. mutans with concentrations ranging from 4.1 mu g/mL to 70.5 mu g/mL No significant activity was found on P. gingivalis except for 4 with an MIC of 6.8 mu g/mL The ability of 1, 1b, 2+3, 4 and 4d to inhibit biofilm formation by S. mutans was evaluated. It was found that 1, 1b, 4 and 4d interfered with the establishment of S. mutans biofilms, inhibiting their development at 32.5, 125.0, 14.1 and 24.4 mu g/mL, respectively. (C) 2012 Elsevier B.V. All rights reserved.