methyl olean-12-en-2β,3β-diol-28-oate | 26563-66-6

• 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: methyl olean-12-en-2β,3β-diol-28-oate
• 英文别名: augustic acid methyl ester；2β,3β-dihydroxy-olean-12-en-28-oic acid methyl ester；2β,3β-Dihydroxy-olean-12-en-28-saeure-methylester；2β.3β-Dihydroxy-Δ¹²-oleanen-28-saeuremethylester；Methyl-2β,3β-dihydroxyolean-12-en-28-oat；methyl (4aS,6aR,6aS,6bR,8aR,10R,11S,12aR,14bS)-10,11-dihydroxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylate
• CAS: 26563-66-6
• 化学式: C₃₁H₅₀O₄
• 分子量: 486.736
• InChiKey: OTDUGESKRJHFHR-VFGSRWGOSA-N

物化性质

• 沸点：
  541.9±50.0 °C(Predicted)
• 密度：
  1.11±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  35
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  三甲基氯硅烷 、 methyl olean-12-en-2β,3β-diol-28-oate 在 吡啶 、 六甲基二硅氮烷 作用下， 反应 0.17h， 生成
  参考文献：
  名称：

  New Triterpenic Saponins from the Aerial Parts of Medicago arabica (L.) Huds

  摘要：

  The reinvestigation of saponin composition from Medicago arabica from Italy allowed the detection of nineteen (1-19) saponins. All of them were purified by reverse-phase chromatography and their structures elucidated by spectroscopic and spectrometric (1D and 2D NMR; ESI-MS/MS) and chemical methods. Fourteen were known saponins, previously found in other plants including other Medicago, species. They have been identified as glycosides of oleanolic acid, 2 beta,3 beta-dihydroxyolean-12-en-28-oic acid, hederagenin, bayogenin and soyasapogenol B. Five saponins, identified as 3-O-[-alpha-L-arabinopyranosyl(1 -> 2)-beta-D-glucuronopyranosyl]-30-O-beta-D-glucopyranosyl 2 beta,3 beta,30-trihydroxyolean-12-en-28-oic acid (1), 3-O-[alpha-L-arabinopyranosyl(1 -> 2)-beta- -D-glucuronopyranosyl]-30-O-[beta-D-glucopyranosyl]3 beta,30-dihydroxyolean-12-en-28-oic acid (2), 3-O-[beta-D-glucuronopyranosyl]-30-O-[alpha-L-arabinopyranosyl(1 -> 2)-beta-D-glucopyranosyl]2 beta,3 beta,30-trihydroxyolean-12-en-28-oic acid (3), 3-O-[beta-D-glucuronopyranosyl]-30-O[alpha-L-arabinopyranosyl(1 -> 2)-beta-D-glucopyranosyl] 3 beta,30-dihydroxyolean-12-en-28-oic acid (4) and 3-O-[beta-D-glucuronopyranosyl]-30-O-[beta-D-glucopyranosyl] 2 beta,3 beta,30-trihydroxyolean-12-en-28-oic acid (5), are reported here as new natural compounds. These new saponins, possessing a hydroxy group at the 30-methyl position of the triterpenic skeleton, have never been previously found in the genus Medicago.

  DOI：

  10.1021/jf8036984
• 作为产物：
  描述：

  齐墩果酸甲酯 在 1,4-二氧六环 、 吡啶 、 四氧化锇 作用下， 生成 methyl olean-12-en-2β,3β-diol-28-oate
  参考文献：
  名称：

  Terpenoids. XXXI.¹ The Structure and Stereochemistry of Medicagenic Acid²

  摘要：

  DOI：

  10.1021/ja01576a057

文献信息

• Oleanen and stigmasterol derivatives from Ambroma augusta
  作者：M.Sarwar Alam、Neeraj Chopra、Mohammed Ali、Masatake Niwa

  DOI：10.1016/0031-9422(95)00774-1

  日期：1996.3

  Abstract Augustic acid, a new oleanane derivative, and a stigmasterol glycoside were isolated from the roots of Ambroma augusta. Their structures were established as olean-12-en-2β,3β-diol-28-oic acid and stigmast-5,22-dien -3-O-α- d -glucopyranoside respectively, on the basis of full spectral analyses and chemical methods.

  摘要 奥古斯都酸、一种新的齐墩果烷衍生物和豆甾醇苷从龙涎香根中分离得到。它们的结构分别为 olean-12-en-2β,3β-diol-28-oic acid 和 stigmast-5,22-dien -3-O-α-d-glupyranoside，基于全光谱分析和化学分析。方法。
• Tschesche et. al., Justus Liebigs Annalen der Chemie, 1964, vol. 676, p. 175,187
  作者：Tschesche et. al.

  DOI：——

  日期：——
• New Triterpenic Saponins from the Aerial Parts of <i>Medicago arabica</i> (L.) Huds
  作者：Aldo Tava、Mariella Mella、Pinarosa Avato、Elisa Biazzi、Luciano Pecetti、Zbigniew Bialy、Marian Jurzysta

  DOI：10.1021/jf8036984

  日期：2009.4.8

  The reinvestigation of saponin composition from Medicago arabica from Italy allowed the detection of nineteen (1-19) saponins. All of them were purified by reverse-phase chromatography and their structures elucidated by spectroscopic and spectrometric (1D and 2D NMR; ESI-MS/MS) and chemical methods. Fourteen were known saponins, previously found in other plants including other Medicago, species. They have been identified as glycosides of oleanolic acid, 2 beta,3 beta-dihydroxyolean-12-en-28-oic acid, hederagenin, bayogenin and soyasapogenol B. Five saponins, identified as 3-O-[-alpha-L-arabinopyranosyl(1 -> 2)-beta-D-glucuronopyranosyl]-30-O-beta-D-glucopyranosyl 2 beta,3 beta,30-trihydroxyolean-12-en-28-oic acid (1), 3-O-[alpha-L-arabinopyranosyl(1 -> 2)-beta- -D-glucuronopyranosyl]-30-O-[beta-D-glucopyranosyl]3 beta,30-dihydroxyolean-12-en-28-oic acid (2), 3-O-[beta-D-glucuronopyranosyl]-30-O-[alpha-L-arabinopyranosyl(1 -> 2)-beta-D-glucopyranosyl]2 beta,3 beta,30-trihydroxyolean-12-en-28-oic acid (3), 3-O-[beta-D-glucuronopyranosyl]-30-O[alpha-L-arabinopyranosyl(1 -> 2)-beta-D-glucopyranosyl] 3 beta,30-dihydroxyolean-12-en-28-oic acid (4) and 3-O-[beta-D-glucuronopyranosyl]-30-O-[beta-D-glucopyranosyl] 2 beta,3 beta,30-trihydroxyolean-12-en-28-oic acid (5), are reported here as new natural compounds. These new saponins, possessing a hydroxy group at the 30-methyl position of the triterpenic skeleton, have never been previously found in the genus Medicago.
• Terpenoids. XXXI.¹ The Structure and Stereochemistry of Medicagenic Acid²
  作者：Carl Djerassi、D. B. Thomas、A. L. Livingston、C. Ray Thompson

  DOI：10.1021/ja01576a057

  日期：1957.10