D-赤型鞘氨醇C-15 | 86555-28-4

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: D-赤型鞘氨醇C-15
• 英文名称: 15-carbon-sphingosine
• 英文别名: So (d15:1)；2S-Amino-4E-pentadecene-1,3R-diol；(E,2S,3R)-2-aminopentadec-4-ene-1,3-diol
• CAS: 86555-28-4
• 化学式: C₁₅H₃₁NO₂
• 分子量: 257.417
• InChiKey: KWQIYZIHZCLRSR-AMXOMPAFSA-N

物化性质

• 溶解度：
  DMF：10mg/mL； DMSO：2mg/mL；乙醇：可混溶

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  18
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  66.5
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  D-赤型鞘氨醇C-15 在 吡啶 、 2,6-二甲基吡啶 、 萘 、 sodium 、 二甲基二环氧乙烷 、 二异丁基氢化铝 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 乙二醇二甲醚 、 二氯甲烷 、 丙酮 、 甲苯 为溶剂， 反应 139.0h， 生成
  参考文献：
  名称：

  Synthesis of (2S,2′R,3S,4R)-2-(2′-Hydroxy-21′-methyldocosanoylamino)- 1,3,4-pentadecanetriol, the Ceramide Sex Pheromone of the Female Hair Crab,…

  摘要：

  以(S)-丝氨酸和 12-溴-1-十二醇为起点，合成了雌性大闸蟹（Erimacrus isenbeckii）的神经酰胺性信息素[(2S,2′R,3S,4R)-2-(2′-羟基-21′-甲基月桂酰氨基)-1,3,4-十五烷三醇（1）]。

  DOI：

  10.1271/bbb.66.1531
• 作为产物：
  描述：

  十三碳-2-炔醛 在 四氢呋喃 、 盐酸 、 甲醇 、 lithium aluminium tetrahydride 、 乙醇 、 potassium carbonate 、 锌 作用下， 生成 D-赤型鞘氨醇C-15
  参考文献：
  名称：

  鞘氨醇和类鞘氨醇化合物†

  摘要：

  描述了几种鞘氨醇型不饱和长链氨基二醇的合成。记录了它们的物理性质和生物活性。

  DOI：

  10.1002/hlca.19590420202

文献信息

• [EN] ARTIFICIALLY SYNTHESIZED SPHINGOSINE DERIVATIVE LIPOID MONOMER AND USE OF SAME FOR DELIVERING NUCLEIC ACID<br/>[FR] MONOMÈRE LIPOÏDE DÉRIVÉ DE SPHINGOSINE SYNTHÉTISÉ ARTIFICIELLEMENT ET SON UTILISATION POUR L'ADMINISTRATION D'ACIDE NUCLÉIQUE<br/>[ZH] 人工合成的鞘氨醇衍生物类脂质单体及其递送核酸的用途
  申请人：INST BASIC MEDICAL SCIENCES CAMS

  公开号：WO2019185038A1

  公开（公告）日：2019-10-03

  本发明提供了人工合成的鞘氨醇类脂质单体及其递送核酸的用途。具体地，本发明提供了使用式I化合物、其立体异构体或其药学上可接受的盐或包含式I的化合物、其立体异构体或其药学上可接受的盐的组合对细胞或受试者递送核酸的用途或方法，(I)
• 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.
• Ceramides: Branched alkyl chains in the sphingolipid siblings of diacylglycerol improve biological potency
  作者：Ji-Hye Kang、Himanshu Garg、Dina M. Sigano、Nicholas Francella、Robert Blumenthal、Victor E. Marquez

  DOI：10.1016/j.bmc.2009.01.005

  日期：2009.2

  The synthesis of a small number of ceramide analogues containing a combination of linear and highly branched alkyl chains on either the D-sphingosine or the N-acyl core of the molecule is reported. Regardless of location, the presence of the branched chain improves potency relative to the positive control, C2 ceramide; however, the most potent compound (4) has the branched side chain as part of the D-sphingosine core. The induction of apoptosis by 4 in terms of Annexin V binding and DiOC(6) labeling was superior to that achieved with C2 ceramide. (c) 2009 Elsevier Ltd. All rights reserved.
• ARTIFICIALLY SYNTHESIZED SPHINGOSINE DERIVATIVE LIPOID MONOMER AND USE OF SAME FOR DELIVERING NUCLEIC ACID
  申请人：INSTITUTE OF BASIC MEDICAL SCIENCES CHINESE ACADEMY OF MEDICAL SCIENCES

  公开号：US20210015767A1

  公开（公告）日：2021-01-21

  The invention provides an artificially synthesized single sphingosine lipid and use of delivering a nucleic acid thereof. More particularly, the invention provides Use or method for delivering a nucleic acid to a cell or a subject using a compound of Formula (I), a stereoisomer or a pharmaceutical acceptable salt thereof, or a combination comprising a compound of Formula (I), a stereoisomer or a pharmaceutical acceptable salt thereof,
• Sphingosin und Sphingosin-ähnliche Verbindungen
  作者：E. F. Jenny、J. Druey

  DOI：10.1002/hlca.19590420202

  日期：——

  The syntheses of several unsaturated long-chain aminodiols of the sphingosine type are described. Their physical properties and biological activities are noted.

  描述了几种鞘氨醇型不饱和长链氨基二醇的合成。记录了它们的物理性质和生物活性。