齐墩果-12-烯-2α,3β,28-三醇 | 14464-51-8

• 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
• 中文名称: 齐墩果-12-烯-2α,3β,28-三醇
• 英文名称: olean-12-en-2α,3β,28-triol
• 英文别名: 2α.3β.28-Trihydroxy-oleanan-(12)；Olean-12-ene-2alpha,3beta,28-triol；(2R,3R,4aR,6aR,6bS,8aS,12aS,14aR,14bR)-8a-(hydroxymethyl)-4,4,6a,6b,11,11,14b-heptamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicene-2,3-diol
• CAS: 14464-51-8
• 化学式: C₃₀H₅₀O₃
• 分子量: 458.725
• InChiKey: XBXOIGGIJQMJBM-VCOXBGKMSA-N

物化性质

• 熔点：
  275-279 °C
• 沸点：
  536.7±50.0 °C(Predicted)
• 密度：
  1.10±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  33
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  60.7
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  齐墩果-12-烯-2α,3β,28-三醇 在 吡啶 、 sodium azide 作用下， 以 二氯甲烷 为溶剂， 反应 40.0h， 生成
  参考文献：
  名称：

  Maslinic acid derivatives induce significant apoptosis in b16f10 murine melanoma cells

  摘要：

  Maslinic acid (2 alpha,3 beta-dihydroxyolean-12-en-28-oic acid), a natural dihydroxylated pentacyclic triterpene acid isolated from olive-pressing residues, has been investigated together with some of its derivatives regarding the induction of apoptosis in B16F10 melanoma cells. Some of the compounds tested are described in this work, but others come from previous studies. Ten of these derivatives induce over 80% of apoptosis, clearly promoting cell death in B16F10 melanoma. By contrast, the induction cell death through necrosis was very slightly significant with these compounds. These results indicate that maslinic acid derivatives are promising chemopreventive and chemotherapeutic agents. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.10.011
• 作为产物：
  描述：

  山楂酸 在 lithium aluminium tetrahydride 、 甲醇 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以93%的产率得到齐墩果-12-烯-2α,3β,28-三醇
  参考文献：
  名称：

  Maslinic acid derivatives induce significant apoptosis in b16f10 murine melanoma cells

  摘要：

  Maslinic acid (2 alpha,3 beta-dihydroxyolean-12-en-28-oic acid), a natural dihydroxylated pentacyclic triterpene acid isolated from olive-pressing residues, has been investigated together with some of its derivatives regarding the induction of apoptosis in B16F10 melanoma cells. Some of the compounds tested are described in this work, but others come from previous studies. Ten of these derivatives induce over 80% of apoptosis, clearly promoting cell death in B16F10 melanoma. By contrast, the induction cell death through necrosis was very slightly significant with these compounds. These results indicate that maslinic acid derivatives are promising chemopreventive and chemotherapeutic agents. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.10.011

文献信息

• Epoxides, Cyclic Sulfites, and Sulfate from Natural Pentacyclic Triterpenoids:  Theoretical Calculations and Chemical Transformations
  作者：Andrés García-Granados、Pilar E. López、Enrique Melguizo、Juan N. Moliz、Andrés Parra、Yolanda Simeó、José A. Dobado

  DOI：10.1021/jo026832s

  日期：2003.6.1

  the A-ring functionalized, were semisynthesized from oleanolic and maslinic acids. The reactivities of sulfites, sulfate, and epoxides in these triterpene compounds were investigated under different reaction conditions. Moreover, contracted A-ring triterpenes (five-membered rings) were obtained, by different treatments of the sulfate 7. From the epoxide 8, deoxygenated and halohydrin derivatives were

  由齐墩果酸和山楂酸半合成具有A环官能化的几种三萜衍生物。在不同的反应条件下，研究了这些三萜化合物中亚硫酸盐，硫酸盐和环氧化物的反应性。此外，通过硫酸盐7的不同处理获得了收缩的A环三萜（五元环）。从环氧化物8中，脱氧的和卤代醇衍生物与几种亲核试剂半合成。臭氧分解反应和贝克曼反应用于从五元环烯丙二烯三萜烯生成4-氮杂化合物。给出了硫酸盐7的X射线结构，并与密度泛函理论几何结构进行了比较。理论上的（13）C和（1）H化学位移（在B3LYP / 6-31G * // B3LYP / 6-31G *水平上的轨距不变原子轨道方法）和（3）J（H，
• Studies on oxidation of triterpenoids: part vii. Transformation of oleanane and ursane skeletons to 11α, 12α-oxidotriterpenoids with hydrogen perox
  作者：Bhim Prasad Pradhan、Satyajit Chakraborty、Peter Weyerstahl

  DOI：10.1016/s0040-4020(01)90326-6

  日期：1987.1

  Hydrogen peroxide-selenium dioxide in -butanol has been found to be a good reagent for the preparation of 11α,12α, -oxidotriterpenoids of oleanane and ursane skeletons; whereas α -amyrin and β-amyrin acetates furnished 11α,12α -epoxyurs-14-en-3β-yl acetate () and 11α, 12α -epoxytaraxer-14-en-3β-yl acetate () respectively, uvaol and ursolic acid/methyl ester gave 11α, 12α -epoxyurs-28→13-olide-3β-ol

  已经发现，在丁醇中的过氧化氢-二氧化硒是制备11α，12α-齐墩果烷和熊烷骨架的-氧化三萜类化合物的良好试剂。而乙酸α-锚蛋白和β-锚蛋白分别提供11α，12α-环氧-urs-14-en-3β-乙酸乙烯酯（）和11α，12α-环氧taraxer-14-en-3β-乙酸乙烯酯（），丁香酚和熊果酸/甲酯得到11α，12α-环氧-28→13-内酰胺-3β-醇（）; 赤藓二醇（）和齐墩果酸（）/甲酯（）生成11α，12α-环氧油酸-28→13-内酰胺-3β-醇（）; oleam-12-en-2α，3β，28-基三乙酸酯（）在相似的反应上提供了11α，12α-epoxytaraxer-14-en-3β-ol-2α，28-yl diacetate（）和11α，12α-epoxytaraxer-14 -en-2α，3β-二醇-28-乙酸乙烯酯（）。
• Triterpenoid constituents of rose-bay willow-herb
  作者：A. T. Glen、W. Lawrie、J. McLean、M. El-Garby Younes

  DOI：10.1039/j39670000510

  日期：——

  The leaves of rose-bay willow-herb (Chamaenerion angustifolium) are shown to contain ursolic acid, oleanolic acid, maslinic acid, and a hitherto unknown acid, 2α-hydroxyursolic acid. A partial synthesis of the new acid is described and some of its derivatives are compared with the corresponding derivatives of the isomeric maslinic acid.

  玫瑰湾柳草（Chamaenerion angustifolium）的叶子显示含有熊果酸，齐墩果酸，山梨酸和迄今未知的酸2α-羟基熊果酸。描述了新酸的部分合成，并将其一些衍生物与异构山梨酸的相应衍生物进行了比较。
• Maslinic acid derivatives induce significant apoptosis in b16f10 murine melanoma cells
  作者：Andres Parra、Francisco Rivas、Samuel Martin-Fonseca、Andres Garcia-Granados、Antonio Martinez

  DOI：10.1016/j.ejmech.2011.10.011

  日期：2011.12

  Maslinic acid (2 alpha,3 beta-dihydroxyolean-12-en-28-oic acid), a natural dihydroxylated pentacyclic triterpene acid isolated from olive-pressing residues, has been investigated together with some of its derivatives regarding the induction of apoptosis in B16F10 melanoma cells. Some of the compounds tested are described in this work, but others come from previous studies. Ten of these derivatives induce over 80% of apoptosis, clearly promoting cell death in B16F10 melanoma. By contrast, the induction cell death through necrosis was very slightly significant with these compounds. These results indicate that maslinic acid derivatives are promising chemopreventive and chemotherapeutic agents. (C) 2011 Elsevier Masson SAS. All rights reserved.