N-dodecanoyl-L-seryl-L-serine dodecyl ester

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-dodecanoyl-L-seryl-L-serine dodecyl ester
• 英文别名: dodecyl (2S)-2-[[(2S)-2-(dodecanoylamino)-3-hydroxypropanoyl]amino]-3-hydroxypropanoate
• 化学式: C₃₀H₅₈N₂O₆
• 分子量: 542.8
• InChiKey: MOFMVLAIGSCMNL-SVBPBHIXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.3
• 重原子数：
  38
• 可旋转键数：
  28
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  125
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  1-(月桂酰氧基)-2,5-吡咯烷二酮 在 氯甲酸乙酯 、 碳酸氢钠 、 三乙胺 作用下， 以 乙二醇二甲醚 、 水 为溶剂， 反应 16.25h， 生成 N-dodecanoyl-L-seryl-L-serine dodecyl ester
  参考文献：
  名称：

  Synthetic ceramide analogues as skin permeation enhancers: structure–Activity relationships

  摘要：

  The study presents new information about the structure-activity relationships of the skin permeation enhancers. A series of ceramide analogues including eight different polar head groups and six different chain lengths was synthesised. The compounds were evaluated as permeation enhancers in vitro using porcine skin. The physico-chemical parameters of the tested compounds obtained by computer modelling were used to evaluate, by multiple linear regression, the enhancement ratios (ERs) of the compounds. The regression analysis suggests that the hydrogen bonding ability of the compounds is inversely related to the ER values and that the molecular size and lipophilicity must be well balanced. In the studied enhancers having the same chain length, the enhancement activity is dependent only on their permeability coefficients. This finding confirms the Warner's hypothesis that the polar head of an enhancer is responsible for the permeation and anchoring of the molecule into the stratum corneum lipids and that it does not influence the mechanism of action. For the specific action of enhancers, that is disordering of the intercellular lipid packing, the length of the hydrophobic chain(s) and not the lipophilicity is important. Furthermore, the examination of the FTIR spectra indicated that the most active substances possess the most ordered chains. The described relationships could bring more rational approaches in designing new potent enhancers for transdermal formulations. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2003.09.034

文献信息

• l-Serine and glycine based ceramide analogues as transdermal permeation enhancers: polar head size and hydrogen bonding
  作者：Kateřina Vávrová、Alexandr Hrabálek、Pavel Doležal、Tomáš Holas、Jarmila Zbytovská

  DOI：10.1016/s0960-894x(03)00409-8

  日期：2003.7

  Novel transdermal permeation enhancers related to stratum corneum ceramides were investigated. The synthesis of a series of simple compounds based on two selected amino acids, L-serine and glycine, and their enhancement activities are reported. Glycine derivative 3 enhanced the permeation of theophylline through human skin in vitro 12.5 +/- 0.5 times. The relationships between properties of the polar head of the compounds and their activity are discussed. (C) 2003 Elsevier Science Ltd. Ail rights reserved.