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Trisnorsqualene alcohol | 118599-25-0

中文名称
——
中文别名
——
英文名称
Trisnorsqualene alcohol
英文别名
4,8,13,17,21-Pentamethyldocosan-1-OL
Trisnorsqualene alcohol化学式
CAS
118599-25-0
化学式
C27H56O
mdl
——
分子量
396.741
InChiKey
XHTUUQNKECQODO-UHFFFAOYSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

物化性质

  • 沸点:
    425.1±13.0 °C(Predicted)
  • 密度:
    0.837±0.06 g/cm3(Predicted)

计算性质

  • 辛醇/水分配系数(LogP):
    11.8
  • 重原子数:
    28
  • 可旋转键数:
    20
  • 环数:
    0.0
  • sp3杂化的碳原子比例:
    1.0
  • 拓扑面积:
    20.2
  • 氢给体数:
    1
  • 氢受体数:
    1

SDS

SDS:2b78bc0b0e85e6a26db52b9b2e960b8c
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反应信息

  • 作为反应物:
    描述:
    Trisnorsqualene alcoholpotassium tert-butylate三乙胺 作用下, 以 二氯甲烷乙腈 、 xylene 为溶剂, 反应 24.5h, 生成 [2,3-bis(4,8,13,17,21-pentamethyl-docosyloxy)propyl](2-hydroxyethyl)dimethylammonium bromide
    参考文献:
    名称:
    Synthesis, characterization and transfection activity of new saturated and unsaturated cationic lipids
    摘要:
    We synthesized new cationic lipids, analogue to N-[1-(2,3-dioleoyloxy)propyl]-N,N,N-trimethylammonium chloride (DOTMA) and 1,2-dimyristyloxypropyl-3-dimethyl-hydroxyethylammonium bromide (DMRIE), in order to compare those containing a dodecyl chain with those having a relatively long chain with two or five double bonds, such as squalenyl and dihydrofarnesyl derivatives, or complex saturated structures, such as squalane derivatives. The fusogenic helper lipid dioleoylphosphatidylethanolamine (DOPE) was added to cationic lipids to form a stable complex. Liposomes composed of 50:50 w/w cationic lipid/DOPE were prepared and incubated with plasmidic DNA at various charge ratios and the diameter and zeta potential of the complexes were measured. The surface charge of the DNA/lipid complexes can be controlled by adjusting the cationic lipid/DNA ratio. Finally, we tested the in vitro transfection efficiency of the cationic lipid/DNA complexes using different cell lines. The transfection efficiency was highest for the dodecyloxy derivative containing a single hydroxyethyl group in the head, followed by the dodecyloxy and the farnesyloxy trimethylammonium derivatives. Instead the C27 squalenyl and C27 squalanyl derivatives resulted inactive.
    DOI:
    10.1016/j.farmac.2004.06.007
  • 作为产物:
    描述:
    1,1',2-trisnorsqualene alcohol 在 palladium on activated charcoal 氢气 作用下, 以 乙醇 为溶剂, 反应 48.0h, 生成 Trisnorsqualene alcohol
    参考文献:
    名称:
    Trisnorsqualene alcohol, a potent inhibitor of vertebrate squalene epoxidase
    摘要:
    DOI:
    10.1021/ja00186a062
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文献信息

  • Trisnorsqualene alcohol, a potent inhibitor of vertebrate squalene epoxidase
    作者:Stephanie E. Sen、Glenn D. Prestwich
    DOI:10.1021/ja00186a062
    日期:1989.2
  • SEN, STEPHANIE E.;PRESTWICH, GLENN D., J. AMER. CHEM. SOC., 111,(1989) N, C. 1508-1510
    作者:SEN, STEPHANIE E.、PRESTWICH, GLENN D.
    DOI:——
    日期:——
  • Synthesis, characterization and transfection activity of new saturated and unsaturated cationic lipids
    作者:Silvia Arpicco、Silvana Canevari、Maurizio Ceruti、Enrico Galmozzi、Flavio Rocco、Luigi Cattel
    DOI:10.1016/j.farmac.2004.06.007
    日期:2004.11
    We synthesized new cationic lipids, analogue to N-[1-(2,3-dioleoyloxy)propyl]-N,N,N-trimethylammonium chloride (DOTMA) and 1,2-dimyristyloxypropyl-3-dimethyl-hydroxyethylammonium bromide (DMRIE), in order to compare those containing a dodecyl chain with those having a relatively long chain with two or five double bonds, such as squalenyl and dihydrofarnesyl derivatives, or complex saturated structures, such as squalane derivatives. The fusogenic helper lipid dioleoylphosphatidylethanolamine (DOPE) was added to cationic lipids to form a stable complex. Liposomes composed of 50:50 w/w cationic lipid/DOPE were prepared and incubated with plasmidic DNA at various charge ratios and the diameter and zeta potential of the complexes were measured. The surface charge of the DNA/lipid complexes can be controlled by adjusting the cationic lipid/DNA ratio. Finally, we tested the in vitro transfection efficiency of the cationic lipid/DNA complexes using different cell lines. The transfection efficiency was highest for the dodecyloxy derivative containing a single hydroxyethyl group in the head, followed by the dodecyloxy and the farnesyloxy trimethylammonium derivatives. Instead the C27 squalenyl and C27 squalanyl derivatives resulted inactive.
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