3-epicycloartenol | 31978-75-3

• 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: 3-epicycloartenol
• 英文别名: (1S,3R,6R,8R,11S,12S,15R,16R)-7,7,12,16-tetramethyl-15-[(2R)-6-methylhept-5-en-2-yl]pentacyclo[9.7.0.01,3.03,8.012,16]octadecan-6-ol
• CAS: 31978-75-3
• 化学式: C₃₀H₅₀O
• 分子量: 426.726
• InChiKey: ONQRKEUAIJMULO-BVEDLWBASA-N

物化性质

• 熔点：
  84 °C
• 沸点：
  505.5±19.0 °C(Predicted)
• 密度：
  1.01±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.8
• 重原子数：
  31
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-epicycloartenol 在 镍 4-异丙基甲苯 作用下， 生成 9,19-cyclolanostan-3-one
  参考文献：
  名称：

  高沸点溶剂中的反应II：阮内镍对三萜类化合物的影响

  摘要：

  研究了阮内镍对沸腾对甲基苯丙醚中三萜类化合物的影响。已经观察到以下三种不同类型的反应：（a）3-OH基团的脱氢（氧化），（b）易还原双键的饱和，以及（c）双键转移至相邻位置在盟友转移中。这种转变具有可逆性。通过该反应，将3-羟基三萜烯盐酸盐转化为3-酮-三萜烯，通过氢解除去Cl原子。还提出了一种机制。

  DOI：

  10.1016/s0040-4020(01)92409-3
• 作为产物：
  描述：

  cycloart-24-en-3-one 在 lithium aluminium tetrahydride 作用下， 生成 3-epicycloartenol
  参考文献：
  名称：

  Cancer Chemopreventive Effects of Cycloartane-Type and Related Triterpenoids in in Vitro and in Vivo Models

  摘要：

  Forty-eight natural and semisynthetic cycloartane-type and related triterpenoids have been evaluated for their inhibitory effects on Epstein-Barr virus early antigen (EBV-EA) activation induced by the tumor promoter 12-O-tetradecanoylphorbol-13-acetate (TPA) in Raji cells as a primary screening test for anti-tumor promoters. In addition, these triterpenoids have been tested for their inhibitory effects on activation of (+/-)-(E)-methtyl-2-[(E)-hydroxyimino]-5-nitro-6-methoxy-3-hexemide (NOR 1), a nitric oxide (NO) donor, as a primary screening test for anti-tumor initiators. All of the compounds tested exhibited inhibitory effects on both EBV-EA and NOR 1 activation. Six of these compounds having a C-24 hydroxylated side chain, viz., (24R)-cycloart-25-ene-3 beta,24-diol (9), (24R)-cycloartane-3 beta,24,25-triol (11), (24S)-cycloartane-3 beta,24,25-triol (12), (24 xi)-24-methylcycloartane-3 beta,24,24(1)-triol (14), (24 xi)-24(1)-methoxy-24-methylcycloartane-3 beta,24-diol (15), and (24 xi)-24,25-dihydroxycycloartan-3-one (27), showed higher inhibitory effects than the others tested on both EBV-EA (IC50 values of 6.1-7.4 nM) and NOR 1 activation. Furthermore, compounds 14 and 15 exhibited inhibitory effects on skin tumor promotion in an in vivo two-stage mouse skin carcinogenesis test using 7,12-dimethylbenz[a]anthracene (DMBA) as an initiator and TPA as a promoter.

  DOI：

  10.1021/np068044u

文献信息

• Reactions in high boiling solvent—II
  作者：S.B. Mahato、S.K. Banerjee、R.N. Chakravarti

  DOI：10.1016/s0040-4020(01)92409-3

  日期：——

  The effect of Raney nickel on triterpenoids in boiling p-cymene has been studied. The following three different types of reactions have been observed: (a) dehydrogenation (oxidation) of the 3-OH group, (b) saturation of the easily reducible double bond, and (c) shifting of the double bond to an adjacent position as in allylic shift. The shift is of reversible nature. A 3-hydroxytriterpenehydrochloride

  研究了阮内镍对沸腾对甲基苯丙醚中三萜类化合物的影响。已经观察到以下三种不同类型的反应：（a）3-OH基团的脱氢（氧化），（b）易还原双键的饱和，以及（c）双键转移至相邻位置在盟友转移中。这种转变具有可逆性。通过该反应，将3-羟基三萜烯盐酸盐转化为3-酮-三萜烯，通过氢解除去Cl原子。还提出了一种机制。
• Cancer Chemopreventive Effects of Cycloartane-Type and Related Triterpenoids in in Vitro and in Vivo Models
  作者：Takashi Kikuchi、Toshihiro Akihisa、Harukuni Tokuda、Motohiko Ukiya、Kenji Watanabe、Hoyoku Nishino

  DOI：10.1021/np068044u

  日期：2007.6.1

  Forty-eight natural and semisynthetic cycloartane-type and related triterpenoids have been evaluated for their inhibitory effects on Epstein-Barr virus early antigen (EBV-EA) activation induced by the tumor promoter 12-O-tetradecanoylphorbol-13-acetate (TPA) in Raji cells as a primary screening test for anti-tumor promoters. In addition, these triterpenoids have been tested for their inhibitory effects on activation of (+/-)-(E)-methtyl-2-[(E)-hydroxyimino]-5-nitro-6-methoxy-3-hexemide (NOR 1), a nitric oxide (NO) donor, as a primary screening test for anti-tumor initiators. All of the compounds tested exhibited inhibitory effects on both EBV-EA and NOR 1 activation. Six of these compounds having a C-24 hydroxylated side chain, viz., (24R)-cycloart-25-ene-3 beta,24-diol (9), (24R)-cycloartane-3 beta,24,25-triol (11), (24S)-cycloartane-3 beta,24,25-triol (12), (24 xi)-24-methylcycloartane-3 beta,24,24(1)-triol (14), (24 xi)-24(1)-methoxy-24-methylcycloartane-3 beta,24-diol (15), and (24 xi)-24,25-dihydroxycycloartan-3-one (27), showed higher inhibitory effects than the others tested on both EBV-EA (IC50 values of 6.1-7.4 nM) and NOR 1 activation. Furthermore, compounds 14 and 15 exhibited inhibitory effects on skin tumor promotion in an in vivo two-stage mouse skin carcinogenesis test using 7,12-dimethylbenz[a]anthracene (DMBA) as an initiator and TPA as a promoter.