18-hydroxy-9(Z)-octadecenamide | 172995-11-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 18-hydroxy-9(Z)-octadecenamide
• 英文别名: (Z)-18-hydroxyoctadec-9-enamide
• CAS: 172995-11-8
• 化学式: C₁₈H₃₅NO₂
• 分子量: 297.481
• InChiKey: COMQWAVNBAURCZ-UPHRSURJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  21
• 可旋转键数：
  16
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  63.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  18-hydroxy-9(Z)-octadecenamide 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 二氯甲烷 、 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 10.0h， 生成 5-(3-{5-[3-((Z)-17-Carbamoyl-heptadec-9-enyloxycarbonyl)-propionylamino]-pentyl}-thioureido)-2-(6-hydroxy-3-oxo-3H-xanthen-9-yl)-benzoic acid
  参考文献：
  名称：

  Structure Determination of an Endogenous Sleep-Inducing Lipid, cis-9-Octadecenamide (Oleamide):  A Synthetic Approach to the Chemical Analysis of Trace Quantities of a Natural Product

  摘要：

  The pursuit of endogenous sleep-inducing substances has been the focus of an extensive, complicated body of research. Several compounds, including Delta-sleep-inducing peptide and prostaglandin D-2, have been suggested to play a role in sleep induction, and yet, the molecular mechanisms of this physiological process remain largely unknown. In recent efforts, the cerebrospinal fluid of deep-deprived cats was analyzed in search of compounds that accumulated during sleep deprivation. An agent with the chemical formula C18H35NO was found to cycle with sleep-wake patterns, increasing in concentration with sleep deprivation and decreasing in amount upon recovery sleep. Since the material was generated in minute quantities and only under the special conditions of sleep deprivation, efforts to isolate sufficient material for adequate characterization, structure identification, and subsequent detailed evaluation of its properties proved unrealistic. With the trace amounts of the impure endogenous compound available, extensive MS studies on the agent were completed, revealing key structural features of the molecule including two degrees of unsaturation, a long alkyl chain, and a nitrogen substituent capable of fragmenting as ammonia. Additionally, HPLC traces suggested a weak UV absorbance for the unknown material. With this data in hand and encouraged by the relatively small size of the molecule, MW = 281, a synthetic approach toward the structural identification of the natural compound was initiated. Herein, we report the full details of the synthesis and comparative characterization of candidate structures for this endogenous agent that led to the unambiguous structural correlation with synthetic cis-9-octadecenamide.

  DOI：

  10.1021/ja9532345
• 作为产物：
  描述：

  (Z)-18-(tert-Butyl-diphenyl-silanyloxy)-octadec-9-enoyl chloride 在 ammonium hydroxide 、 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 2.08h， 生成 18-hydroxy-9(Z)-octadecenamide
  参考文献：
  名称：

  Structure Determination of an Endogenous Sleep-Inducing Lipid, cis-9-Octadecenamide (Oleamide):  A Synthetic Approach to the Chemical Analysis of Trace Quantities of a Natural Product

  摘要：

  The pursuit of endogenous sleep-inducing substances has been the focus of an extensive, complicated body of research. Several compounds, including Delta-sleep-inducing peptide and prostaglandin D-2, have been suggested to play a role in sleep induction, and yet, the molecular mechanisms of this physiological process remain largely unknown. In recent efforts, the cerebrospinal fluid of deep-deprived cats was analyzed in search of compounds that accumulated during sleep deprivation. An agent with the chemical formula C18H35NO was found to cycle with sleep-wake patterns, increasing in concentration with sleep deprivation and decreasing in amount upon recovery sleep. Since the material was generated in minute quantities and only under the special conditions of sleep deprivation, efforts to isolate sufficient material for adequate characterization, structure identification, and subsequent detailed evaluation of its properties proved unrealistic. With the trace amounts of the impure endogenous compound available, extensive MS studies on the agent were completed, revealing key structural features of the molecule including two degrees of unsaturation, a long alkyl chain, and a nitrogen substituent capable of fragmenting as ammonia. Additionally, HPLC traces suggested a weak UV absorbance for the unknown material. With this data in hand and encouraged by the relatively small size of the molecule, MW = 281, a synthetic approach toward the structural identification of the natural compound was initiated. Herein, we report the full details of the synthesis and comparative characterization of candidate structures for this endogenous agent that led to the unambiguous structural correlation with synthetic cis-9-octadecenamide.

  DOI：

  10.1021/ja9532345

文献信息

• A synthetic, mineral oil free, forming oil composition dispersed in a hydroalcoholic medium
  申请人：CENTRO SVILUPPO MATERIALI S.p.A.

  公开号：EP0591771A1

  公开（公告）日：1994-04-13

  Described is a forming oil composition, on synthetic basis, free from mineral oils, dispersed in a hydroalcoholic medium. Said forming oil can be applied by spraying, rolling or immersion, or other convenient methods, be it directly on coils, be it in the forming department. After drying, the forming oil yields a removable organic film (R.O.F.).

  所描述的是一种成型油组合物，以合成油为基础，不含矿物油，分散在水醇介质中。这种成型油可以通过喷洒、滚动、浸泡或其他方便的方法涂抹，可以直接涂抹在线圈上，也可以在成型部涂抹。干燥后，成型油会产生一层可去除的有机膜（R.O.F.）。
• MOISTURE-RESISTANT SKIN TREATMENT COMPOSITIONS
  申请人：CHARLES OF THE RITZ GROUP LTD.

  公开号：EP0292554A1

  公开（公告）日：1988-11-30
• EP0292554A4
  申请人：——

  公开号：EP0292554A4

  公开（公告）日：1989-02-22
• INHIBITORS OF GAP JUNCTION COMMUNICATION
  申请人：The Scripps Research Institute

  公开号：EP1039902A2

  公开（公告）日：2000-10-04
• EP1039902A4
  申请人：——

  公开号：EP1039902A4

  公开（公告）日：2002-07-17