2α,3β,24-trihydroxyolean-12-en-28-oic acid methyl ester | 136338-87-9

• 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: 2α,3β,24-trihydroxyolean-12-en-28-oic acid methyl ester
• 英文别名: methyl 2α,3β,24-trihydroxyolean-12-en-28-oate；methyl arjunolate；methyl (4aS,6aR,6aS,6bR,8aR,9S,10R,11R,12aR,14bS)-10,11-dihydroxy-9-(hydroxymethyl)-2,2,6a,6b,9,12a-hexamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylate
• CAS: 136338-87-9
• 化学式: C₃₁H₅₀O₅
• 分子量: 502.735
• InChiKey: PQQIABJSQBQEFM-QUPLQXSNSA-N

物化性质

• 沸点：
  575.7±50.0 °C(Predicted)
• 密度：
  1.15±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  36
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  87
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2α,3β,24-trihydroxyolean-12-en-28-oic acid methyl ester 在 lithium bromide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 以90%的产率得到2α,3β,24-trihydroxyolean-12-en-28-oic acid
  参考文献：
  名称：

  Remote Hydroxylation of Methyl Groups by Regioselective Cyclopalladation. Partial Synthesis of Hyptatic Acid-A

  摘要：

  Hyptatic acid-A (32), a 2 alpha,3 beta,24-trihydroxyolean-12-en-28-oic acid, previously isolated from Hyptis capitata, was obtained from maslinic acid (2). The regioselective cyclopalladation of the axial methyl group on C-4 of maslinic acid afforded the C-24 hydroxymethylene group due to the presence of a C-2-OR substituent. Nevertheless, hederagenin (7) (23-hydroxy derivative) was formed when this oxygenated group was not present.

  DOI：

  10.1021/jo070116e
• 作为产物：
  描述：

  methyl 2α-acetoxy-3β-hydroxyolean-12-en-28-oate 在 吡啶 、 盐酸 、 氢氧化钾 、 sodium tetrahydroborate 、 jones reagent 、 titanium(III) chloride 、 盐酸羟胺 、 ammonium acetate 作用下， 以 四氢呋喃 、 甲醇 、 水 、 异丙醇 、 丙酮 为溶剂， 反应 19.0h， 生成 2α,3β,24-trihydroxyolean-12-en-28-oic acid methyl ester
  参考文献：
  名称：

  Remote Hydroxylation of Methyl Groups by Regioselective Cyclopalladation. Partial Synthesis of Hyptatic Acid-A

  摘要：

  Hyptatic acid-A (32), a 2 alpha,3 beta,24-trihydroxyolean-12-en-28-oic acid, previously isolated from Hyptis capitata, was obtained from maslinic acid (2). The regioselective cyclopalladation of the axial methyl group on C-4 of maslinic acid afforded the C-24 hydroxymethylene group due to the presence of a C-2-OR substituent. Nevertheless, hederagenin (7) (23-hydroxy derivative) was formed when this oxygenated group was not present.

  DOI：

  10.1021/jo070116e

文献信息

• Wang; Li; Li, Pharmazie, 2001, vol. 56, # 5, p. 420 - 422
  作者：Wang、Li、Li、Li

  DOI：——

  日期：——
• DIALLO, BILO;VANHAELEN, M.;VANHAELEN-FASTRE, R.;KONOSHIMA, TAKAO;KOZUKA, +, J. NATUR. PROD., 52,(1989) N, C. 879-881
  作者：DIALLO, BILO、VANHAELEN, M.、VANHAELEN-FASTRE, R.、KONOSHIMA, TAKAO、KOZUKA, +

  DOI：——

  日期：——
• Triterpene phytoalexins from nectarine fruits
  作者：Hassane El Lahlou、Nobuhiro Hirai、Mitsuya Tsuda、Hajime Ohigashi

  DOI：10.1016/s0031-9422(99)00316-7

  日期：1999.10

  Seven triterpenoid phytoalexins were isolated from peel of unripe fruits of nectarine (Prunus persica cv Fantasia) wounded and inoculated with Colletotrichum musae. Two were new triterpenoids, identified as 1 beta,2 alpha,3 alpha,24-tetrahydroxyurs-12-en-28-oic acid and 1 beta,2 alpha,3 alpha,24-tetrahydroxyolean-12-en-28-oic acid. 2 alpha,3 alpha,24-Trihydroxyolean-12-en-28-oic acid, 2 alpha,3 alpha,24-trihydroxyurs-12-en-28-oic acid, 2 alpha,3 beta,24-trihydroxyolean-12-en-28-oic acid, 2 alpha,3 alpha-dihydroxyolean-12-en-28-oic acid, and 2 alpha,3 alpha-dihydroxyurs-12-en-28-oic acid were previously reported as constitutive natural products from other plants, but were never described as phytoalexins. All showed antifungal activity against the fungus mentioned. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Majumdar, Kakoli; Biswas, Maya; Som, Journal of the Indian Chemical Society, 2005, vol. 82, # 7, p. 673 - 674
  作者：Majumdar, Kakoli、Biswas, Maya、Som、Das, Saktipada

  DOI：——

  日期：——
• Remote Hydroxylation of Methyl Groups by Regioselective Cyclopalladation. Partial Synthesis of Hyptatic Acid-A
  作者：Andrés García-Granados、Pilar E. López、Enrique Melguizo、Andrés Parra、Yolanda Simeó

  DOI：10.1021/jo070116e

  日期：2007.4.1

  Hyptatic acid-A (32), a 2 alpha,3 beta,24-trihydroxyolean-12-en-28-oic acid, previously isolated from Hyptis capitata, was obtained from maslinic acid (2). The regioselective cyclopalladation of the axial methyl group on C-4 of maslinic acid afforded the C-24 hydroxymethylene group due to the presence of a C-2-OR substituent. Nevertheless, hederagenin (7) (23-hydroxy derivative) was formed when this oxygenated group was not present.