L'OREAL, Fundamental Research, 1 avenue Eugene Schueller, 93600 Aulnay-sous-Bois, France.
Int J Cosmet Sci. 1995 Aug;17(4):133-46. doi: 10.1111/j.1467-2494.1995.tb00116.x.
Synopsis 2-N-Oleoylamino-octadecane-1,3-diol is a new synthetic ceramide. The process enables a four-step preparation of 2-amino-octadecane-1,3-diol (D,L-erythro/threo) and a five-step synthesis of 2-N-oleoylamino-octadecane-1,3-diol (D,L-erythro/threo). The latter compound is related to ceramide 2 according to the classification of Downing. This route of synthesis is rapid, reproducible and uses low-cost starting materials. The new ceramide was analysed as follows: (1)H, (13)C, (15)N NMR spectra afforded an unambiguous characterization of the structure; additionally, these three methods identified the threo and erythro isomers. (1)H and (13)C NMR permitted the measurement of the threo/erythro ratio (26.6/73.4 and 25.5/74.5, respectively). Chemical ionization mass spectrometry confirmed the expected mass of the pseudo-molecular ion (m/z= 566.5: M + H) as well as the presence of different chain lengths other than the oleic moiety due to the fatty acid composition of the technical grade oleic acid used for the synthesis. Capillary gas chromatography measured the threo/erythro ratio (23.5/76.5) which agrees with the (1)H and (13)C NMR data. Moreover, this method afforded the relative distribution of the different N-acylated chains. The properties of the new synthetic ceramide for the treatment of skin and hair were mainly assessed by two in vitro methods. The first measured the flux of water through lipid-extracted stratum corneum. The described ceramide showed high efficacy in decreasing water loss. The second recorded the friction coefficient of different types of hair: virgin, permanent-waved, and bleached. Treatment by the ceramide led to a strong decrease in this coefficient. This was particularly observed on unrinsed hair. These findings suggest two potential fields of application and beneficial contribution for the new ceramide: repairing the barrier to transepidermal water loss, and improving the surface properties of hair. Synthèse du 2-N-oleoylamino-octadécane-1,3-diol: nouveau céramide à haut potentiel dans le soin de la peau et du cheveu.
2-N-油酰氨基-十八烷-1,3-二醇是一种新型合成神经酰胺。该工艺能够通过四步制备 2-氨基-十八烷-1,3-二醇（D,L-erythro/threo）和五步合成 2-N-油酰氨基-十八烷-1,3-二醇（D,L-erythro/threo）。根据 Downing 的分类，后者化合物与神经酰胺 2 有关。该合成路线快速、可重复且使用低成本的起始原料。新的神经酰胺如下进行分析：（1）H、（13）C、（15）N NMR 谱提供了结构的明确特征；此外，这三种方法还确定了 threo 和 erythro 异构体。（1）H 和（13）C NMR 允许测量 threo/erythro 比值（分别为 26.6/73.4 和 25.5/74.5）。化学电离质谱证实了预期的准分子离子的质量（m/z=566.5：M+H)以及由于用于合成的技术级油酸的脂肪酸组成，除了油酰部分之外存在不同链长的存在。毛细管气相色谱法测量了 threo/erythro 比值（23.5/76.5），与（1）H 和（13）C NMR 数据一致。此外，该方法提供了不同 N-酰化链的相对分布。新型合成神经酰胺治疗皮肤和头发的性质主要通过两种体外方法进行评估。第一种方法测量经脂质提取的角质层通过的水通量。所述神经酰胺显示出在减少水分流失方面的高效。第二种方法记录了不同类型头发的摩擦系数：原始、永久性波浪和漂白。用神经酰胺处理会导致该系数强烈下降。这在未冲洗的头发上尤其明显。这些发现表明了新型神经酰胺的两个潜在应用领域和有益贡献：修复经表皮水分流失的屏障，以及改善头发的表面性质。
