2-O-acetyl-tetracosanoic acid | 58249-16-4

• 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: 2-O-acetyl-tetracosanoic acid
• 英文别名: SFAHFA 2:0/24:0；DL-2-Acetoxy-tetracosansaeure；DL-2-acetoxy-tetracosanoic acid；2-acetoxy-tetracosanoic acid；(R,S)-2-acetoxy-tetracosanoic acid；2-Acetoxytetracosanoic acid；2-acetyloxytetracosanoic acid
• CAS: 58249-16-4
• 化学式: C₂₆H₅₀O₄
• 分子量: 426.681
• InChiKey: USHLGTXWTJINJU-UHFFFAOYSA-N

物化性质

• 熔点：
  64-66 °C
• 沸点：
  525.7±33.0 °C(Predicted)
• 密度：
  0.935±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  11.3
• 重原子数：
  30
• 可旋转键数：
  24
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-O-acetyl-tetracosanoic acid 在 TEA 、 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 76.0h， 生成 半乳糖苷神经酰胺
  参考文献：
  名称：

  Quantitative Measurements of Recombinant HIV Surface Glycoprotein 120 Binding to Several Glycosphingolipids Expressed in Planar Supported Lipid Bilayers

  摘要：

  The interaction of recombinant HIV-1 surface glycoprotein gp120 (rgp120) with natural isolates of lactosylceramide (LacCer), glucosylceramide (GlcCer), and galactosylceramide (GaiCer) has been quantitatively measured under equilibrium conditions using total internal reflection fluorescence (TIRF) spectroscopy. The binding affinity (K-a) of rgp120 to these glycosphingolipids (GSLs), reconstituted at 5 mol % in supported planar lipid bilayers composed of 95 mol % POPC, is ca. 10(6) M-1 for dissolved rgp120 concentrations greater than 25 nM. In contrast, at concentrations of rgp120 between 0.2 and 15 nM, rgp120 does not bind significantly to LacCer and GlcCer, but has a high affinity for GalCer with a measured K-a value of 1.6 x 10(9) M-1. However, protein surface coverage measurements show that this strong binding process accounts for very little of the total protein adsorbed over the entire concentration range studied. At a protein concentration of ca. 20 nM, the surface coverage is only 3% of that achieved at apparent saturation (i.e., when the protein concentration is ca. 220 nM). Thus the "high affinity" binding sites comprise only a small fraction of the total number of binding sites. Several other variables were investigated, Rgp120 binding behavior at membranes doped with alpha-hydroxygalactosylceramide (alpha-GalCer) was very similar to that observed with GalCer, showing that the presence/absence of an alpha-hydroxy moiety does not significantly affect galactosylceramide recognition. Phase segregation of GalCer, which occurs when the mole fraction of this GSL in a POPC bilayer exceeds ca. 0.1, was also investigated and showed no effect on binding affinity at low rgp120 concentrations. To investigate the influence of fatty acid chain length, GSLs with monodisperse C-18 and C-24 chain lengths, both with and without an alpha-hydroxy moiety, were synthesized, and their binding affinity to rgp120 was examined. Relative to the natural isolates (which contain a mixture of chain lengths), minimal differences were observed; thus among the compounds tested, fatty acid chain length does not affect GSL recognition. The results of this work should aid efforts to design anti-HIV-1 agents based on membrane-tethered, carbohydrate-based receptors for rgp120.

  DOI：

  10.1021/ja011225s
• 作为产物：
  描述：

  2-羟基二十四烷酸 在 吡啶 、 乙酸酐 作用下， 以 正己烷 、 水 为溶剂， 生成 2-O-acetyl-tetracosanoic acid
  参考文献：
  名称：

  Selective N-acylation of amino alcohols

  摘要：

  本发明提供了一种高效的方法，通过选择性酰化氨基醇的自由胺与有机酸或其盐，与烷基磺酰氯或烷基苯磺酰氯反应，在有机溶剂和有机碱的存在下形成相应的混合酐，然后与氨基醇或其盐反应形成相应的N-酰基氨基醇。

  公开号：

  US05631356A1

文献信息

• NOVEL MEDICINAL COMPOSITION
  申请人：KIRIN BEER KABUSHIKI KAISHA

  公开号：EP0650732A1

  公开（公告）日：1995-05-03

  A medicinal composition comprising at least one compound represented by general formula (A), specifically a myeloid cell growth promoter, a radiation damage protective and a thrombocytopenia remedy, wherein R represents (α), (R₂ being H or OH, and X being an integer of 0 to 26) or -(CH₂)₇CH=CH(CH₂)₇CH₃; R₁ represents a substituent selected from the group consisting of -CH₂(CH₂)YCH₃, -CH(OH)(CH₂)YCH₃, -CH(OH)(CH₂)YCH(CH₃)₂ and -CH=CH(CH₂)YCH₃; and Y represents an integer of 5 to 17.

  一种药物组合物，包含至少一种由通式(A)代表的化合物，特别是一种髓系细胞生长促进剂、一种辐射损伤保护剂和一种血小板减少治疗剂，其中 R 代表(α)，(R₂为 H 或 OH，X 为 0 至 26 的整数)或-(CH₂)₇CH=CH(CH₂)₇CH₃；R₁ 代表选自以下组成的组的取代基：-CH₂(CH₂)YCH₃、-CH(OH)(CH₂)YCH₃、-CH(OH)(CH₂)YCH(CH₃)₂ 和 -CH=CH(CH₂)YCH₃；以及 Y 代表 5 至 17 的整数。
• Klenk; Clarenz, Hoppe-Seyler's Zeitschrift fur Physiologische Chemie, 1939, vol. 257, p. 274
  作者：Klenk、Clarenz

  DOI：——

  日期：——
• Chibnall; Piper; Williams, Biochemical Journal, 1953, vol. 55, p. 713
  作者：Chibnall、Piper、Williams

  DOI：——

  日期：——
• NOVEL SPHINGOGLYCOLIPID AND USE THEREOF
  申请人：KIRIN BEER KABUSHIKI KAISHA

  公开号：EP0609437B1

  公开（公告）日：1999-07-07
• SELECTIVE N-ACYLATION OF AMINO ALCOHOLS
  申请人：GIST-BROCADES N.V.

  公开号：EP0633875A1

  公开（公告）日：1995-01-18