coussaric acid methyl ester 24-monoacetate | 625434-10-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: coussaric acid methyl ester 24-monoacetate
• 英文别名: methyl (1S,4aR,6aR,6aS,6bR,8aR,9S,10R,12aR,14bS)-9-(acetyloxymethyl)-1,10-dihydroxy-1,6a,6b,9,12a-pentamethyl-2-methylidene-4,5,6,6a,7,8,8a,10,11,12,13,14b-dodecahydro-3H-picene-4a-carboxylate
• CAS: 625434-10-8
• 化学式: C₃₃H₅₀O₆
• 分子量: 542.756
• InChiKey: AQOCOHNAQNXZOY-XVYCUCPZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  39
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  93.1
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  甲氧基-三氟甲基苯 、 coussaric acid methyl ester 24-monoacetate 在 4-二甲氨基吡啶 、 deuterated pyridine 作用下， 生成 methyl (1S,4aR,6aR,6aS,6bR,8aR,9S,10R,12aR,14bS)-9-(acetyloxymethyl)-1,6a,6b,9,12a-pentamethyl-2-methylidene-1,10-bis[[(2R)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoyl]oxy]-4,5,6,6a,7,8,8a,10,11,12,13,14b-dodecahydro-3H-picene-4a-carboxylate
  参考文献：
  名称：

  Isolation and absolute stereochemistry of coussaric acid, a new bioactive triterpenoid from the stems of Coussarea brevicaulis

  摘要：

  Coussaric acid (1), a triterpenoid based on an ursane skeleton, and an oleanane-type triterpene acid, 3-epi-spathodic acid (2), as well as four known compounds, barbinervic acid, scutellaric acid, stigmasterol and stigmasterol glucoside, have been isolated from an EtOAc-soluble extract of the stems of Coussarea brevicaulis. The structures of compounds 1 and 2 were elucidated on the basis of spectroscopic investigation, and single-crystal X-ray crystallography was used to confirm the structure of 1. The absolute stereochemistry of 1 was established by chemical transformations and by the Mosher ester procedure. The potential of the isolates and chemical transformation products to induce quinone reductase was evaluated in mouse Hepa lclc7 hepatoma cells. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0031-9422(03)00268-1
• 作为产物：
  描述：

  乙酸酐 、 coussaric acid 在 吡啶 作用下， 以2.2 mg的产率得到coussaric acid methyl ester 24-monoacetate
  参考文献：
  名称：

  Isolation and absolute stereochemistry of coussaric acid, a new bioactive triterpenoid from the stems of Coussarea brevicaulis

  摘要：

  Coussaric acid (1), a triterpenoid based on an ursane skeleton, and an oleanane-type triterpene acid, 3-epi-spathodic acid (2), as well as four known compounds, barbinervic acid, scutellaric acid, stigmasterol and stigmasterol glucoside, have been isolated from an EtOAc-soluble extract of the stems of Coussarea brevicaulis. The structures of compounds 1 and 2 were elucidated on the basis of spectroscopic investigation, and single-crystal X-ray crystallography was used to confirm the structure of 1. The absolute stereochemistry of 1 was established by chemical transformations and by the Mosher ester procedure. The potential of the isolates and chemical transformation products to induce quinone reductase was evaluated in mouse Hepa lclc7 hepatoma cells. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0031-9422(03)00268-1