11,20-dihydroxy-12-methoxyabiet-8,11,13-triene

• 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: 11,20-dihydroxy-12-methoxyabiet-8,11,13-triene
• 英文别名: 11,20-dihydroxy-12-methoxy-abiet-8,11,13-triene；(4bR,8aS)-4b-(hydroxymethyl)-3-methoxy-8,8-dimethyl-2-propan-2-yl-5,6,7,8a,9,10-hexahydrophenanthren-4-ol
• 化学式: C₂₁H₃₂O₃
• 分子量: 332.483
• InChiKey: ZULNZVBUWODPIZ-HRAATJIYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  鼠尾草酸 在 Nocardia sp. NRRL 5646 作用下， 以 DMF (N,N-dimethyl-formamide) 、 水 为溶剂， 反应 24.0h， 生成 鼠尾草苦内脂 、 11,20-dihydroxy-12-methoxyabiet-8,11,13-triene 、 11,12,16,17-tetrahydroxy-7,10-(epoxymethano)abiet-8,11,13-triene-20-one
  参考文献：
  名称：

  Novel derivatives of carnosic acid

  摘要：

  使用Nocardia sp.，NRRL 5646进行孵育，以产生新的阿比特烷二萜化学保护剂和抗氧化剂卡诺酸的衍生物。将C-20羧酸官能团还原，然后在C-12酚上进行甲基化，得到新化合物11,20-二羟基-12-甲氧基-阿比-8,11,13-三烯。将卡诺酸氧化环化为卡诺索，然后在异丙基部分进行二羟基化，得到新化合物11,12,16,17-四羟基-7-10-(环氧甲氧基)-阿比-8,11,13-三烯-20-酮。通过质谱和核磁共振光谱分析确认了这些新卡诺酸衍生物的结构。利用2,2-二苯基-1-苯基肼基自由基清除试验显示，新代谢产物的自由基清除性能优于混合生育酚和卡诺酸。

  公开号：

  US20040014808A1

文献信息

• [EN] NOVEL DERIVATIVES OF CARNOSIC ACID<br/>[FR] NOUVEAUX DERIVES D'ACIDE CARNOSIQUE
  申请人：KEMIN IND INC

  公开号：WO2003087316A2

  公开（公告）日：2003-10-23

  Incubations with Nocardia sp., NRRL 5646 were conducted to produce new derivatives of the abietane-diterpene chemoprotectant and antioxidant, carnosic acid. Reduction of the C-20 carboxylic acid functional group followed by methylation at the C-12 phenol afforded the novel compound 11,20-dihydroxy-12-methoxy-abiet-8,11,13-triene. Oxidative cyclization of carnosic acid to carnosol followed by dihydroxylation at the isopropyl moiety afforded the novel compound 11,12,16,17-tetrahydroxy-7-10-(epoxymethano)-abiet-8,11,13-triene-20-one. The metabolites are new carnosic acid derivatives whose structures were confirmed by mass spectrometry and NMR spectroscopic analysis. The radical quenching properties of the new metabolites using the 2,2-diphenyl-1-picrylhydrazyl (DPPH) free-radical scavenging assay showed activities improved over that of mixed tocopherols and carnosic acid.
• Novel derivatives of carnosic acid
  申请人：——

  公开号：US20040014808A1

  公开（公告）日：2004-01-22

  Incubations with Nocardia sp., NRRL 5646 were conducted to produce new derivatives of the abietane-diterpene chemoprotectant and antioxidant, carnosic acid. Reduction of the C-20 carboxylic acid functional group followed by methylation at the C-12 phenol afforded the novel compound 11,20-dihydroxy-12-methoxy-abiet-8,11,13-triene. Oxidative cyclization of carnosic acid to carnosol followed by dihydroxylation at the isopropyl moiety afforded the novel compound 11,12,16,17-tetrahydroxy-7-10-(epoxymethano)-abiet-8,11,13-triene-20-one. The metabolites are new carnosic acid derivatives whose structures were confirmed by mass spectrometry and NMR spectroscopic analysis. The radical quenching properties of the new metabolites using the 2,2-diphenyl-1-picrylhydrazyl (DPPH) free-radical scavenging assay showed activities improved over that of mixed tocopherols and carnosic acid.

  使用Nocardia sp.，NRRL 5646进行孵育，以产生新的阿比特烷二萜化学保护剂和抗氧化剂卡诺酸的衍生物。将C-20羧酸官能团还原，然后在C-12酚上进行甲基化，得到新化合物11,20-二羟基-12-甲氧基-阿比-8,11,13-三烯。将卡诺酸氧化环化为卡诺索，然后在异丙基部分进行二羟基化，得到新化合物11,12,16,17-四羟基-7-10-(环氧甲氧基)-阿比-8,11,13-三烯-20-酮。通过质谱和核磁共振光谱分析确认了这些新卡诺酸衍生物的结构。利用2,2-二苯基-1-苯基肼基自由基清除试验显示，新代谢产物的自由基清除性能优于混合生育酚和卡诺酸。