rac-1-O-octadecyl-2-O-palmitoylglycerol 3-phosphate | 103383-65-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 甘油磷脂
• 英文名称: rac-1-O-octadecyl-2-O-palmitoylglycerol 3-phosphate
• 英文别名: rac-2-O-hexadecanoyl-3-O-octadecylglycero-3-phosphate；1-octadecyloxy-2-palmitoyloxy-3-phosphonooxy-propane；1-Octadecyloxy-2-palmitoyloxy-3-phosphonooxy-propan；(1-Octadecoxy-3-phosphonooxypropan-2-yl) hexadecanoate
• CAS: 103383-65-9
• 化学式: C₃₇H₇₅O₇P
• 分子量: 662.972
• InChiKey: OHMWCXDRHYCCRS-UHFFFAOYSA-N

物化性质

• 熔点：
  65-66 °C
• 沸点：
  713.9±70.0 °C(Predicted)
• 密度：
  0.982±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  14.4
• 重原子数：
  45
• 可旋转键数：
  38
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.97
• 拓扑面积：
  102
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  rac-1-O-octadecyl-2-O-palmitoylglycerol 3-phosphate 、 1-β-D-arabinofuranosylcytosine 5'-monophosphoromorpholidate 4-morpholine N,N'-dicyclohexylcarboxamidinium salt 在 吡啶 作用下， 反应 120.0h， 以29%的产率得到1-beta-D-阿拉伯糖呋喃基胞嘧啶 5'-二磷酸酯-1-O-十八烷基-2-O-棕榈酰-甘油
  参考文献：
  名称：

  Nucleoside conjugates. 7. Synthesis and antitumor activity of 1-.beta.-D-arabinofuranosylcytosine conjugates of ether lipids

  摘要：

  Three new 1-beta-D-arabinofuranosylcytosine conjugates of ether lipids (alkyl glycerols) linked by a pyrophosphate diester bond have been prepared and evaluated against mouse leukemia L1210 and P388. These include ara-CDP-rac-1-O-hexadecyl-2-O-palmitoylglycerol (9a) (ara-CDP = 1-beta-D-arabinofuranosylcytosine 5'-diphosphate), ara-CDP-rac-1-O-octadecyl-2-O-palmitoylglycerol (9b), and ara-CDP-rac-1-O-octadecyl-2-O-methylglycerol (9c). Among them, conjugate 9a produced significant increase in life span (200-293%) in mice bearing ip and ic implanted L1210 lymphoic leukemia at a total dose of 400-500 mg (406-508 mumol/kg). Significant schedule dependence was not observed when the conjugate was given ip once daily on day 1, days 1, 5, and 9, and days 1-5. The new conjugates are water soluble by sonication.

  DOI：

  10.1021/jm00160a041
• 作为产物：
  描述：

  鲨肝醇 在 platinum(IV) oxide 吡啶 、 咪唑 、 四丁基氟化铵 、 氢气 作用下， 以 四氢呋喃 、 环己烷 、 溶剂黄146 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 126.0h， 生成 rac-1-O-octadecyl-2-O-palmitoylglycerol 3-phosphate
  参考文献：
  名称：

  Sahai, Parmeshwari; Vishwakarma, Ram A., Journal of the Chemical Society. Perkin transactions I, 1997, # 12, p. 1845 - 1849

  摘要：

  DOI：

文献信息

• Stegerhoek; Verkade, Recueil des Travaux Chimiques des Pays-Bas, 1956, vol. 75, p. 467,473
  作者：Stegerhoek、Verkade

  DOI：——

  日期：——
• Nucleoside conjugates. 7. Synthesis and antitumor activity of 1-.beta.-D-arabinofuranosylcytosine conjugates of ether lipids
  作者：Chung Il Hong、Seung Ho An、David J. Buchheit、Alexander Nechaev、Alan J. Kirisits、Charles R. West、Wolfgang E. Berdel

  DOI：10.1021/jm00160a041

  日期：1986.10

  Three new 1-beta-D-arabinofuranosylcytosine conjugates of ether lipids (alkyl glycerols) linked by a pyrophosphate diester bond have been prepared and evaluated against mouse leukemia L1210 and P388. These include ara-CDP-rac-1-O-hexadecyl-2-O-palmitoylglycerol (9a) (ara-CDP = 1-beta-D-arabinofuranosylcytosine 5'-diphosphate), ara-CDP-rac-1-O-octadecyl-2-O-palmitoylglycerol (9b), and ara-CDP-rac-1-O-octadecyl-2-O-methylglycerol (9c). Among them, conjugate 9a produced significant increase in life span (200-293%) in mice bearing ip and ic implanted L1210 lymphoic leukemia at a total dose of 400-500 mg (406-508 mumol/kg). Significant schedule dependence was not observed when the conjugate was given ip once daily on day 1, days 1, 5, and 9, and days 1-5. The new conjugates are water soluble by sonication.
• Sahai, Parmeshwari; Vishwakarma, Ram A., Journal of the Chemical Society. Perkin transactions I, 1997, # 12, p. 1845 - 1849
  作者：Sahai, Parmeshwari、Vishwakarma, Ram A.

  DOI：——

  日期：——