(2S,3S,4R)-2-[(2'S)-2'-hydroxyoctadecanoylamino]-1,3,4-octadecantriol | 154801-29-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 鞘脂
• 英文名称: (2S,3S,4R)-2-[(2'S)-2'-hydroxyoctadecanoylamino]-1,3,4-octadecantriol
• 英文别名: N-((S)-α-hydroxyoctadecanoyl)phytosphingosine；Octadecanamide, N-((1S,2S,3R)-2,3-dihydroxy-1-(hydroxymethyl)heptadecyl)-2-hydroxy-, (2S)-；(2S)-2-hydroxy-N-[(2S,3S,4R)-1,3,4-trihydroxyoctadecan-2-yl]octadecanamide
• CAS: 154801-29-3
• 化学式: C₃₆H₇₃NO₅
• 分子量: 599.979
• InChiKey: BBAFBDLICMHBNU-SNSGHMKVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.6
• 重原子数：
  42
• 可旋转键数：
  33
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.97
• 拓扑面积：
  110
• 氢给体数：
  5
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  N-(2-hydroxystearoyl)phytosphingosine 生成 (2S,3S,4R)-2-[(2'R)-2'-hydroxyoctadecanoylamino]-1,3,4-octadecantriol 、 (2S,3S,4R)-2-[(2'S)-2'-hydroxyoctadecanoylamino]-1,3,4-octadecantriol
  参考文献：
  名称：

  Polymorphism of ceramide 6: a vibrational spectroscopic and X-ray powder diffraction investigation of the diastereomers of N-(α-hydroxyoctadecanoyl)-phytosphingosine

  摘要：

  A preparative chromatographic method was developed for the quantitative isolation of the diastereomers of synthetic N-(alpha-hydroxyoctadecanoyl)-phytosphingosine (DL-CER6). The (L)- and the (D)-compound were studied each by means X-ray powder diffraction, FT-Raman and FT-IR spectroscopy. The diastereomers exhibit different thermotropic polymorphism. Three lamellar crystalline and a lamellar liquid crystalline phase were found for L-CER6. The natural occurring D-CER6 forms an La phase with a larger repeating distance than the L-CER6. The two lamellar crystalline phases of the D-compound have a significant larger dimension than those of the L-compound. The addition of water lowers the phase transition temperatures but does not induce structural changes such as incorporation into the lamellar sheets. (C) 2004 Elsevier Ireland Ltd. All rights reserved.

  DOI：

  10.1016/j.chemphyslip.2004.09.015

文献信息

• Polymorphism of ceramide 6: a vibrational spectroscopic and X-ray powder diffraction investigation of the diastereomers of N-(α-hydroxyoctadecanoyl)-phytosphingosine
  作者：Steve Raudenkolb、Siegfried Wartewig、R.H.H. Neubert

  DOI：10.1016/j.chemphyslip.2004.09.015

  日期：2005.1

  A preparative chromatographic method was developed for the quantitative isolation of the diastereomers of synthetic N-(alpha-hydroxyoctadecanoyl)-phytosphingosine (DL-CER6). The (L)- and the (D)-compound were studied each by means X-ray powder diffraction, FT-Raman and FT-IR spectroscopy. The diastereomers exhibit different thermotropic polymorphism. Three lamellar crystalline and a lamellar liquid crystalline phase were found for L-CER6. The natural occurring D-CER6 forms an La phase with a larger repeating distance than the L-CER6. The two lamellar crystalline phases of the D-compound have a significant larger dimension than those of the L-compound. The addition of water lowers the phase transition temperatures but does not induce structural changes such as incorporation into the lamellar sheets. (C) 2004 Elsevier Ireland Ltd. All rights reserved.