(Z)-Octadec-9-enoic acid (S)-2-hexadecyloxy-1-hydroxymethyl-ethyl ester | 95403-80-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 甘油脂
• 英文名称: (Z)-Octadec-9-enoic acid (S)-2-hexadecyloxy-1-hydroxymethyl-ethyl ester
• 英文别名: 1-O-Hexadecyl-2-(9Z-octadecenoyl)-sn-glycerol；[(2S)-1-hexadecoxy-3-hydroxypropan-2-yl] (Z)-octadec-9-enoate
• CAS: 95403-80-8
• 化学式: C₃₇H₇₂O₄
• 分子量: 580.976
• InChiKey: ZDRGKGZHXIWXJD-MEVCPPAWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14.6
• 重原子数：
  41
• 可旋转键数：
  35
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (Z)-Octadec-9-enoic acid (S)-2-hexadecyloxy-1-hydroxymethyl-ethyl ester 在 水 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 生成
  参考文献：
  名称：

  从克氏锥虫的脂质中含有不饱和脂肪酸的生物活性糖基磷脂酰肌醇的化学合成。

  摘要：

  DOI：

  10.1002/anie.200502779
• 作为产物：
  描述：

  鲛肝醇 在 吡啶 、 4-二甲氨基吡啶 、 triethylamine tris(hydrogen fluoride) 、 三乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 3.0h， 生成 (Z)-Octadec-9-enoic acid (S)-2-hexadecyloxy-1-hydroxymethyl-ethyl ester
  参考文献：
  名称：

  从克氏锥虫的脂质中含有不饱和脂肪酸的生物活性糖基磷脂酰肌醇的化学合成。

  摘要：

  DOI：

  10.1002/anie.200502779

文献信息

• The α Isoform of Diacylglycerol Kinase Exhibits Arachidonoyl Specificity with Alkylacylglycerol
  作者：Richard M. Epand、Angela Kam、Nadia Bridgelal、Akihiko Saiga、Matthew K. Topham

  DOI：10.1021/bi0484724

  日期：2004.11.1

  We compared the diacylglycerol kinase (DGK) catalyzed phosphorylation of 1-O-hexanoyl-2-oleoylglycerol (HOG) with 1-O-hexanoyl-2-arachidonoylglycerol (HAG). We assayed the activity of DGKalpha and DGKzeta using a liposomal-based assay system. Liposomal assays show that the DGKalpha and, to a lesser extent, DGKzeta preferentially act on substrates containing an arachidonoyl group when this group is incorporated into alkylacylglycerols. The activity of DGKalpha was 82 times greater with HAG compared to HOG. DGK is 10 times more active in catalyzing the phosphorylation of HAG compared to HOG. Although diacylglycerols were better substrates for both DGKalpha and DGKzeta than the alkylacylglycerols, no specificity was exhibited for arachidonoyl-containing diacylglycerols. However, this specificity for HAG over HOG is modulated by the phospholipid composition of the liposome. Addition of cholesterol and/or phosphatidylethanolamine partially reduces the substrate selectivity. We also analyzed the kinetic constants for the phosphorylation of both diacylglycerol and 1-alkyl-2-acylglycerol catalyzed by the alpha, epsilon, or isoforms using a soluble Triton mixed micelle system. We found that all three isoforms of DGK can phosphorylate 1-alkyl-2-acylglycerols but generally at a lower rate than for the corresponding diacylglycerol. The specificity of DGKepsilon for diacylglycerols containing an arachidonoyl group was retained when the ester group in the C-1 position is replaced with an ether linkage. In contrast, DGKalpha and, to a lesser extent, DGKzeta had greater specificity for arachidonoyl-containing 1-alkyl-2-acylglycerols than for arachidonoyl-containing diacylglycerols. This demonstrates that the acyl chain specificity is affected by the structure of the lipid headgroup.
• METHOD OF ENHANCING TRANSMUCOSAL DELIVERY OF THERAPEUTIC COMPOUNDS
  申请人：Quay C. Steven

  公开号：US20070077283A1

  公开（公告）日：2007-04-05

  A composition comprising a biologically active agent and a permeation enhancing lipid wherein the permeation enhancing lipid is a platelet activating factor antagonist or a biologically inactive a platelet activating factor, and increases permeability of the biologically active agent across a tissue layer. Also disclosed is a process of increasing the permeability of a biological agent across a layer tissue comprising contacting the tissue layer with a composition comprising the biological agent and a permeation enhancing lipid wherein the permeation enhancing lipid is a platelet activating factor antagonist or a biologically inactive platelet activating factor.