(R)-17-hydroxy octadecanoic acid | 35433-70-6

• 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: (R)-17-hydroxy octadecanoic acid
• 英文别名: (17R)-17-hydroxystearic acid；(17R)-17-hydroxyoctadecanoic acid
• CAS: 35433-70-6
• 化学式: C₁₈H₃₆O₃
• 分子量: 300.482
• InChiKey: CKGPXFKOAGKQDN-QGZVFWFLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  21
• 可旋转键数：
  16
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-17-hydroxy octadecanoic acid 在 sodium dichromate 、 硫酸 、 三氟化硼 、 溶剂黄146 作用下， 以 水 为溶剂， 反应 4.33h， 生成 甲基17-氧代硬脂酸酯
  参考文献：
  名称：

  Properties of unusual phospholipids. III: Synthesis, monolayer investigations and DSC studies of hydroxy octadeca(e)noic acids and diacylglycerophosphocholines derived therefrom

  摘要：

  Diacylglycerophosphocholines containing (R)-3-, (R)-12-, (R)-17-hydroxy octadeca(e)noic acids and the corresponding racemates were synthesized and purified to homogeneity. The influence of the position of the hydroxy group on the monolayer packing properties of these fatty acids and their phosphatidylcholines was studied by Langmuir techniques and 1,2-di-[(R)-12-hydroxy-octadec-cis-9-enyl]-sn-glycero-3-phosphocholine displayed the largest lift-off area (330 Angstrom(2)/molecule). This result was in line with the thermotropic phase behavior of these phospholipids, as measured by differential scanning calorimetry (DSC): the gel-to liquid-crystalline phase transition temperature (T-m) passed through a minimum of -15.1 degrees C for 1,2-di-[(R)-12-hydroxy-octadec-cis-9-enyl]-sn-glycero-3-phosphocholine. (C) 1997 Elsevier Science Ireland Ltd.

  DOI：

  10.1016/s0009-3084(97)00085-6
• 作为产物：
  描述：

  (+)-(S)-17-hydroxystearic acid methyl ester 在 吡啶 、 氢氧化钾 、 potassium acetate 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 30.0h， 生成 (R)-17-hydroxy octadecanoic acid
  参考文献：
  名称：

  Properties of unusual phospholipids. III: Synthesis, monolayer investigations and DSC studies of hydroxy octadeca(e)noic acids and diacylglycerophosphocholines derived therefrom

  摘要：

  Diacylglycerophosphocholines containing (R)-3-, (R)-12-, (R)-17-hydroxy octadeca(e)noic acids and the corresponding racemates were synthesized and purified to homogeneity. The influence of the position of the hydroxy group on the monolayer packing properties of these fatty acids and their phosphatidylcholines was studied by Langmuir techniques and 1,2-di-[(R)-12-hydroxy-octadec-cis-9-enyl]-sn-glycero-3-phosphocholine displayed the largest lift-off area (330 Angstrom(2)/molecule). This result was in line with the thermotropic phase behavior of these phospholipids, as measured by differential scanning calorimetry (DSC): the gel-to liquid-crystalline phase transition temperature (T-m) passed through a minimum of -15.1 degrees C for 1,2-di-[(R)-12-hydroxy-octadec-cis-9-enyl]-sn-glycero-3-phosphocholine. (C) 1997 Elsevier Science Ireland Ltd.

  DOI：

  10.1016/s0009-3084(97)00085-6

文献信息

• Properties of unusual phospholipids. III: Synthesis, monolayer investigations and DSC studies of hydroxy octadeca(e)noic acids and diacylglycerophosphocholines derived therefrom
  作者：Lars Negelmann、Sandra Pisch、Uwe Bornscheuer、Rolf D Schmid

  DOI：10.1016/s0009-3084(97)00085-6

  日期：1997.11

  Diacylglycerophosphocholines containing (R)-3-, (R)-12-, (R)-17-hydroxy octadeca(e)noic acids and the corresponding racemates were synthesized and purified to homogeneity. The influence of the position of the hydroxy group on the monolayer packing properties of these fatty acids and their phosphatidylcholines was studied by Langmuir techniques and 1,2-di-[(R)-12-hydroxy-octadec-cis-9-enyl]-sn-glycero-3-phosphocholine displayed the largest lift-off area (330 Angstrom(2)/molecule). This result was in line with the thermotropic phase behavior of these phospholipids, as measured by differential scanning calorimetry (DSC): the gel-to liquid-crystalline phase transition temperature (T-m) passed through a minimum of -15.1 degrees C for 1,2-di-[(R)-12-hydroxy-octadec-cis-9-enyl]-sn-glycero-3-phosphocholine. (C) 1997 Elsevier Science Ireland Ltd.