(S)-12-hydroxyheptadecanoic acid | 1393082-53-5

• 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: (S)-12-hydroxyheptadecanoic acid
• 英文别名: (12S)-12-hydroxyheptadecanoic acid
• CAS: 1393082-53-5
• 化学式: C₁₇H₃₄O₃
• 分子量: 286.455
• InChiKey: UGNYDWLENCPIBP-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  20
• 可旋转键数：
  15
• 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：

  (S)-12-hydroxyheptadecanoic acid 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 、 potassium hydroxide 作用下， 以 乙二醇二甲醚 、 二氯甲烷 、 水 为溶剂， 反应 20.0h， 生成 (S)-12-[(R)-α-methoxy-α-phenylacetyloxy]heptadecanoic acid methyl ester
  参考文献：
  名称：

  Resin glycosides from the aerial parts of Operculina turpethum

  摘要：

  Three glycosidic acids, turpethic acids A-C, and two intact resin glycosides, turpethosides A and B, all having a common pentasaccharide moiety and 12-hydroxy fatty acid aglycones of different chain lengths, were obtained from the aerial parts of Operculina turpethum. Their structures were elucidated by spectroscopic analyses and chemical correlations. The aglycones were characterized as 12-hydroxypentadecanoic acid in two compounds, 12-hydroxyhexadecanoic acid in two other components, and 12-hydroxyheptadecanoic acid in the fifth compound, which were all confirmed by synthesis. The absolute configurations of these aglycones were all established as S by Mosher's method. These compounds represent the first examples of resin glycosides with a monohydroxylated 12-hydroxy fatty acid as an aglycone, and one compound is the first described resin glycoside having a hydroxylated C-17 fatty acid as its aglycone. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2012.05.010
• 作为产物：
  描述：

  12-L-羟基-5,8,10-十七碳三烯酸 生成 (S)-12-hydroxyheptadecanoic acid
  参考文献：
  名称：

  LEIS, H. J.;HOHENESTER, E.;GLEISPACH, H.;MALLE, E.;MAYER, B., BIOMED. AND ENVIRON. MASS SPECTROM., 14,(1987) N 11, 617-621

  摘要：

  DOI：

文献信息

• Resin glycosides from the aerial parts of Operculina turpethum
  作者：Wenbing Ding、Zi-Hua Jiang、Ping Wu、Liangxiong Xu、Xiaoyi Wei

  DOI：10.1016/j.phytochem.2012.05.010

  日期：2012.9

  Three glycosidic acids, turpethic acids A-C, and two intact resin glycosides, turpethosides A and B, all having a common pentasaccharide moiety and 12-hydroxy fatty acid aglycones of different chain lengths, were obtained from the aerial parts of Operculina turpethum. Their structures were elucidated by spectroscopic analyses and chemical correlations. The aglycones were characterized as 12-hydroxypentadecanoic acid in two compounds, 12-hydroxyhexadecanoic acid in two other components, and 12-hydroxyheptadecanoic acid in the fifth compound, which were all confirmed by synthesis. The absolute configurations of these aglycones were all established as S by Mosher's method. These compounds represent the first examples of resin glycosides with a monohydroxylated 12-hydroxy fatty acid as an aglycone, and one compound is the first described resin glycoside having a hydroxylated C-17 fatty acid as its aglycone. (C) 2012 Elsevier Ltd. All rights reserved.
• LEIS, H. J.;HOHENESTER, E.;GLEISPACH, H.;MALLE, E.;MAYER, B., BIOMED. AND ENVIRON. MASS SPECTROM., 14,(1987) N 11, 617-621
  作者：LEIS, H. J.、HOHENESTER, E.、GLEISPACH, H.、MALLE, E.、MAYER, B.

  DOI：——

  日期：——