N-肉豆蔻酰-D-赤型-鞘氨醇

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 鞘脂
• 中文名称: N-肉豆蔻酰-D-赤型-鞘氨醇
• 英文名称: Tetradecanoic acid ((E)-(1S,2S)-2-hydroxy-1-hydroxymethyl-heptadec-3-enyl)-amide
• 英文别名: N-[(E,2S,3S)-1,3-dihydroxyoctadec-4-en-2-yl]tetradecanamide
• 化学式: C₃₂H₆₃NO₃
• 分子量: 509.857
• InChiKey: ZKRPGPZHULJLKJ-SNCOJOGJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.8
• 重原子数：
  36
• 可旋转键数：
  28
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  69.6
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  三苯基氯甲烷 、 N-肉豆蔻酰-D-赤型-鞘氨醇 在 吡啶 作用下， 以 四氢呋喃 为溶剂， 生成 DL-threo-1-(Triphenylmethoxy)-2-myristoylamino-3-hydroxy-trans-octadecen-(4)
  参考文献：
  名称：

  Sphingolipide, 1. Mitt.: Synthese ceramidähnlicher Verbindungen

  摘要：

  DOI：

  10.1007/bf00899954
• 作为产物：
  描述：

  4-十八碳炔-1,3-二醇,2-氨基-,(2S,3R)- 在 吡啶 、 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 生成 N-肉豆蔻酰-D-赤型-鞘氨醇
  参考文献：
  名称：

  Sphingolipide, 1. Mitt.: Synthese ceramidähnlicher Verbindungen

  摘要：

  DOI：

  10.1007/bf00899954

文献信息

• Inhibitory activity of a ceramide library on interleukin-4 production from activated T cells
  作者：Jin Park、Qian Li、Young-Tae Chang、Tae Sung Kim

  DOI：10.1016/j.bmc.2005.01.027

  日期：2005.4

  Allergic diseases are hypersensitivity disorders associated with the production of specific immunoglobulin E (IgE) to environmental allergens. Interleukin (IL)-4, produced primarily by CD4(+) T cells, is an important stimulus for the switch of the antibody isotype to IgE in both mice and humans. In this study we investigated the inhibitory activity of IL-4 production in activated T cells by screening ceramide derivatives prepared by solid phase combinatorial chemistry. Many ceramide derivatives significantly inhibited IL-4 production in T cells. In particular, ceramide derivatives with a lauroyl group showed strong inhibitory activities on IL-4 production in both phorbol 12-myristate 13-acetate (PMA)-activated EL4 T cells and antigen-primed cells, suggesting that they can be used as compounds for the development of anti-allergic agents. (c) 2005 Elsevier Ltd. All rights reserved.
• The Synthesis and Biological Characterization of a Ceramide Library
  作者：Young-Tae Chang、Jaehwa Choi、Sheng Ding、Eva E. Prieschl、Thomas Baumruker、Jae-Mok Lee、Sung-Kee Chung、Peter G. Schultz

  DOI：10.1021/ja017576o

  日期：2002.3.1

  A facile synthesis of a combinatorial ceramide library and their activities in the NF-kappaB pathway and in apoptosis induction/prevention were demonstrated. A novel NF-kappaB activating molecule was discovered among ceramide containing beta-galactose, and the structural requirements of ceramides for apoptosis induction was elucidated.
• Sphingolipide, 1. Mitt.: Synthese ceramidähnlicher Verbindungen
  作者：M. Klepp、H. Libert、L. Schmid

  DOI：10.1007/bf00899954

  日期：1967.3