(3β,12α) 3,12-diacetoxy-olean-28-oic acid 28,13-lactone | 85031-73-8

• 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: (3β,12α) 3,12-diacetoxy-olean-28-oic acid 28,13-lactone
• 英文别名: 3β,12α-diacetoxy-13-hydroxy-oleanan-28-oic acid-lactone；3β,12α-Diacetoxy-13-hydroxy-oleanan-28-saeure-lacton；[(1S,4S,5R,8R,10S,13R,14R,16S,17S,18R)-16-acetyloxy-4,5,9,9,13,20,20-heptamethyl-23-oxo-24-oxahexacyclo[15.5.2.01,18.04,17.05,14.08,13]tetracosan-10-yl] acetate
• CAS: 85031-73-8
• 化学式: C₃₄H₅₂O₆
• 分子量: 556.783
• InChiKey: PHYDMGIRKRRCER-HFTPXWKKSA-N

物化性质

• 熔点：
  241-243 °C
• 沸点：
  609.9±55.0 °C(Predicted)
• 密度：
  1.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  40
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  78.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (3β,12α) 3,12-diacetoxy-olean-28-oic acid 28,13-lactone 在 氨 、 lithium 作用下， 生成 齐墩果酸
  参考文献：
  名称：

  The chemical and biological potential of C ring modified triterpenoids

  摘要：

  A convenient and elegant route has been developed to separate the natural regioisomers triterpenoids ursolic acid (UA) and oleanolic acid (OA) as well as derivatives thereof. Eleven unknown derivatives of OA were designed, synthesized, and their cytotoxicity was investigated. Further sixteen compounds were prepared to correlate all compounds in a SAR study. It could be shown that C-ring modifications of OA and UA have only a moderate influence onto the cytotoxic activity of the compounds but a significant impact onto the ability to trigger apoptosis in ovarian cancer cells (cell line A2780). (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.11.025
• 作为产物：
  描述：

  齐墩果酸 在 吡啶 、 臭氧 作用下， 以 甲醇 、 氯仿 为溶剂， 反应 3.5h， 生成 (3β,12α) 3,12-diacetoxy-olean-28-oic acid 28,13-lactone
  参考文献：
  名称：

  由齐墩果酸和山梨酸部分合成C环衍生物。通过化学和光化学异构化过程形成数个三烯系统

  摘要：

  从橄榄油压榨固体废物中所含的齐墩果酸半合成了一些在C环上改性的三萜类化合物。齐墩果酸和山lin酸的相应酯使产物具有二烯体系，其通过电环反应产生类似于维生素原D 2的油烯酮。这些化合物的化学和光化学异构化反应产生了两种不同的三烯，其结构与速甾醇和维生素D 2相似。

  DOI：

  10.1016/j.tet.2003.12.023

文献信息

• 18. Triterpenoids. Part V. Some relative configurations in rings<scp>C</scp>,<scp>D</scp>, and<scp>E</scp>of the β-amyrin and the lupeol group of triterpenoids
  作者：D. H. R. Barton、N. J. Holness

  DOI：10.1039/jr9520000078

  日期：——
• Tutin; Naunton, Journal of the Chemical Society, 1913, vol. 103, p. 2050,2057
  作者：Tutin、Naunton

  DOI：——

  日期：——
• Aumueller et al., Justus Liebigs Annalen der Chemie, 1935, vol. 517, p. 211,222
  作者：Aumueller et al.

  DOI：——

  日期：——
• 262. Triterpene resinols and related acids. Part XI. The oxidation of acetyloleanolic acid and of methyl acetyloleanolate with perbenzoic acid
  作者：C. W. Picard、F. S. Spring

  DOI：10.1039/jr9400001387

  日期：——
• The chemical and biological potential of C ring modified triterpenoids
  作者：Bianka Siewert、Jana Wiemann、Alexander Köwitsch、René Csuk

  DOI：10.1016/j.ejmech.2013.11.025

  日期：2014.1

  A convenient and elegant route has been developed to separate the natural regioisomers triterpenoids ursolic acid (UA) and oleanolic acid (OA) as well as derivatives thereof. Eleven unknown derivatives of OA were designed, synthesized, and their cytotoxicity was investigated. Further sixteen compounds were prepared to correlate all compounds in a SAR study. It could be shown that C-ring modifications of OA and UA have only a moderate influence onto the cytotoxic activity of the compounds but a significant impact onto the ability to trigger apoptosis in ovarian cancer cells (cell line A2780). (C) 2013 Elsevier Masson SAS. All rights reserved.