methyl N-(1-oxo-octadecyl)-L-alaninate | 122315-69-9

• 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: methyl N-(1-oxo-octadecyl)-L-alaninate
• 英文别名: N-n-octadecanoyl methyl (L)-alaninate；N-stearoyl-L-alanine methyl ester；N-Stearoyl-L-alanin-methylester；methyl N-(1-oxooctadecyl)-L-alaninate；n-Stearoyl-l-alanine methyl ester；methyl (2S)-2-(octadecanoylamino)propanoate
• CAS: 122315-69-9；52558-77-7
• 化学式: C₂₂H₄₃NO₃
• 分子量: 369.588
• InChiKey: RNRAOYMRAIMUJA-FQEVSTJZSA-N

物化性质

• 熔点：
  76.5-77 °C
• 沸点：
  482.4±18.0 °C(Predicted)
• 密度：
  0.920±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.8
• 重原子数：
  26
• 可旋转键数：
  19
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl N-(1-oxo-octadecyl)-L-alaninate 在 sodium hydroxide 、 盐酸 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 4.0h， 以91%的产率得到N-十八酰基-L-丙氨酸
  参考文献：
  名称：

  新的N-酰基氨基酸和可再生脂肪酸的衍生物：烃的凝胶化和热学性质

  摘要：

  这项工作报告了从C16：0，C18：0，C18：1和C18：1（OH）脂肪酸家族合成新的脂肪N-酰基氨基酸和N-酰基氨基酯的过程，并证明了这些化合物作为有机凝胶的活性代理商。将化合物加热溶解在各种溶剂中（Ñ己烷，甲苯和汽油）。只有饱和C16：0和C18：从丙氨酸衍生0能够形成凝胶的甲苯溶液，和饱和的C16：从苯丙氨酸衍生的0表明胶凝Ñ正己烷。这是l的脂肪N-酰基氨基酯和N-酰基氨基酸衍生物的第一个证据-丝氨酸和脂肪酸C16：0，C18：0和C18：1能够与己烷形成凝胶。该观察证实了1-丝氨酸的片段衍生物中的羟基在形成良好凝胶中的重要性。

  DOI：

  10.1016/j.tetlet.2012.03.015
• 作为产物：
  描述：

  L-丙氨酸甲酯盐酸盐 、 十八烷酰氯 在 potassium hydrogencarbonate 、 三乙胺 作用下， 以 氯仿 、 水 为溶剂， 反应 5.0h， 以95%的产率得到methyl N-(1-oxo-octadecyl)-L-alaninate
  参考文献：
  名称：

  Molecular mechanism of physical gelation of hydrocarbons by fatty acid amides of natural amino acids

  摘要：

  A variety of fatty acid amides of different naturally occurring L-amino acids have been synthesized and they are found to form gels with various hydrocarbons. The gelation properties of these compounds were studied by a number of physical methods including FTIR spectroscopy, X-ray diffraction, scanning electron microscopy, differential scanning calorimetry, rheology, and it was found that gelation depended critically on the fatty acid chain length and the nature of the amino acid. Among them L-alanine based gelators were found to be the most efficient and versatile gelators as they self-assemble into a layered structure to form the gel network. Mechanisms for the assembly and formation of gels from these molecules are discussed. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.05.028

文献信息

• <i>In situ</i> formation of AuNPs using fatty <i>N</i>-acylamino hydrazide organogelators as templates
  作者：Renata Ongaratto、Naiane Conte、Caroline R. Montes D’Oca、Rafael C. Brinkerhoff、Caroline Pires Ruas、Marcos Alexandre Gelesky、Marcelo G. Montes D’Oca

  DOI：10.1039/c8nj04127j

  日期：——

  N-acylamino hydrazides in various nonpolar and polar solvents (n-hexane, toluene, benzene, cyclohexane, and ethanol). Fatty N-acylamino hydrazide derived of the glycine and stearic acid (C18:0) did not form gels in any of the tested solvents. All other hydrazides did form gels in at least two of the organic solvents tested. The morphology of each gel was observed via scanning electron microscopy. The organogels

  这项工作首次报道了新的脂肪N-酰基氨基酰肼的合成，并证明了这些化合物作为低分子量有机胶凝剂和金纳米颗粒（AuNPs）制备模板的活性。最初，我们评估脂肪酸的凝胶化性能Ñ在各种非极性和极性溶剂-酰基酰肼（Ñ己烷，甲苯，苯，环己烷和乙醇）。由甘氨酸和硬脂酸（C18：0）衍生的脂肪N-酰氨基酰肼在任何测试的溶剂中均未形成凝胶。所有其他酰肼确实在至少两种测试的有机溶剂中形成了凝胶。通过观察每个凝胶的形态扫描电子显微镜。衍生自丙氨酸，缬氨酸和苯丙氨酸的有机凝胶具有半透明的特性，而丝氨酸有机凝胶则是不透明的。之后，实现了在有机胶凝剂的存在下使用微波辐射的AuNP的合成。有机胶凝剂还原HAuCl 4，显示530至543 nm之间的等离激元能带峰。另外，该方法不需要还原剂，还原剂通常是污染和毒性的潜在来源。因此，这项工作证实了新型脂肪N-酰基氨基酰肼中的酰肼基在凝胶形成中以及作为制备AuNPs的有机胶凝剂的重要性。
• Cosmetic composition
  申请人：Ajinomoto Co., Inc.

  公开号：EP0928608A2

  公开（公告）日：1999-07-14

  An N-long-chain acyl neutral amino acid ester containing a straight-chain or branched-chain, saturated or unsaturated acyl group having from 6 to 22 carbon atoms, where the hydrocarbon group of the alcohol constituting the ester is a straight-chain or branched-chain, saturated or unsaturated hydrocarbon group having from 1 to 10 carbon atoms disclosed herein is an oily material suitable for cosmetic compositions, which provide an excellent feeling upon use and also an excellent hair conditioning effect to a cosmetic composition containing the same. Further, an ultraviolet ray-absorbing composition characterized by containing, as active ingredients, an ultraviolet ray absorbent, and the above-mentioned N-long-chain acyl neutral amino acid ester or/and an N-long-chain acyl acidic amino acid diester containing a straight-chain or branched-chain, saturated or unsaturated acyl group having from 6 to 22 carbon atoms, where the hydrocarbon group of the alcohol constituting the ester is a straight-chain or branched-chain, saturated or unsaturated hydrocarbon group having from 1 to 10 carbon atoms is an ultraviolet ray-absorbing composition which stabilizes the sparingly-soluble ultraviolet ray absorbent contained therein, and which is also excellent in feeling. Still further, an inorganic pigment composition characterized by containing, as active ingredients, an inorganic pigment and the above-mentioned N-long-chain acyl neutral amino acid ester or/and the above-mentioned N-long-chain acyl acidic amino acid diester is an inorganic pigment composition which is excellent in the dispersion (stability) of the inorganic pigment, which is less irritative to the skin, and which is also excellent in a feeling upon use because of lack of stickiness or the like.

  本发明公开了一种含有直链或支链、饱和或不饱和酰基（具有 6 至 22 个碳原子）的 N-长链酰基中性氨基酸酯，其中构成该酯的醇的烃基是直链或支链、饱和或不饱和烃基（具有 1 至 10 个碳原子），是一种适用于化妆品组合物的油性材料，使用时可提供极佳的触感，对含有该材料的化妆品组合物也具有极佳的头发护理效果。 此外，一种紫外线吸收组合物，其特征在于，作为活性成分，含有紫外线吸收剂和上述 N-长链酰基中性氨基酸酯或/和 N-长链酰基酸性氨基酸二酯，其中 N-长链酰基酸性氨基酸二酯含有直链或支链、具有 6 至 22 个碳原子的饱和或不饱和酰基、其中构成酯的醇的烃基是具有 1 至 10 个碳原子的直链或支链、饱和或不饱和烃基的紫外线吸收组合物，这种紫外线吸收组合物可以稳定其中所含的少溶性紫外线吸收剂，而且具有良好的手感。 此外，一种无机颜料组合物，其特征在于作为有效成分含有无机颜料和上述 N-长链酰基中性氨基酸酯或/和上述 N-长链酰基酸性氨基酸二酯，是一种无机颜料组合物，该无机颜料组合物在无机颜料的分散性（稳定性）方面非常出色，对皮肤的刺激性较小，并且由于没有粘性等，使用时的感觉也非常出色。
• Pharmaceutical composition comprising propofol
  申请人：Novaliq GmbH

  公开号：EP2332525A1

  公开（公告）日：2011-06-15

  The invention provides novel pharmaceutical compositions comprising the active ingredient propofol. Preferably, propofol is dissolved in at least one semifluorinated alkane. The compositions, which are preferably liquid or gel-like, may optionally comprise further excipients. They may be used as fill material in capsules, as buccal or nasal sprays, or as aerosols for pulmonary administration. They are particularly useful for the transmucosal administration of propofol.

  本发明提供了包含活性成分异丙酚的新型药物组合物。异丙酚最好溶解在至少一种半氟化烷烃中。这种组合物最好是液体或凝胶状，也可以选择加入其他辅料。它们可用作胶囊的填充材料、口腔或鼻腔喷雾剂，或用作肺部给药的气雾剂。它们尤其适用于异丙酚的经粘膜给药。
• Composition having gelling properties for the prolonged delivery of bioactive substances
  申请人：Leroux Jean-Christophe

  公开号：US20060121115A1

  公开（公告）日：2006-06-08

  The invention relates to a heat-sensitive composition in liquid form, containing: an organic hydrophobic liquid; an organogelling substance, the molecules of which can be bound to one another by low energy linkages; and a bioactive substance, which switches to organogel form upon coming into contact with a physiological fluid during the administration thereof into an animal body, in particular, a human.

  本发明涉及一种液态热敏组合物，其中包含：一种有机疏水性液体；一种有机胶凝物质，其分子之间可通过低能量连接相互结合；以及一种生物活性物质，在动物体内（尤其是人体）给药过程中，该生物活性物质与生理液体接触后会转变为有机胶凝形式。
• Potential anti-inflammatory actions of the elmiric (lipoamino) acids
  作者：Sumner H. Burstein、Jeffrey K. Adams、Heather B. Bradshaw、Cristian Fraioli、Ronald G. Rossetti、Rebecca A. Salmonsen、John W. Shaw、J. Michael Walker、Robert E. Zipkin、Robert B. Zurier

  DOI：10.1016/j.bmc.2007.03.026

  日期：2007.5

  A library of amino acid-fatty acid conjugates (elmiric acids) was synthesized and evaluated for activity as potential anti-inflammatory agents. The compounds were tested in vitro for their effects on cell proliferation and prostaglandin production, and compared with their effects on in vivo models of inflammation. LPS stimulated RAW 267.4 mouse macrophage cells were the in vitro model and phorbol ester-induced mouse ear edema served as the principal in vivo model. The prostaglandin responses were found to be strongly dependent on the nature of the fatty acid part of the molecule. Polyunsaturated acid conjugates produced a marked increase in media levels of i15-deoxy-PGJ(2) with minimal effects on PGE production. It is reported in the literature that prostaglandin ratios in which the J series predominates over the E series promote the resolution of inflammatory conditions. Several of the elmiric acids tested here produced such favorable ratios suggesting that their potential anti-inflammatory activity occurs via a novel mechanism of action. The ear edema assay results were generally in agreement with the prostaglandin assay findings indicating a connection between them. (c) 2007 Elsevier Ltd. All rights reserved.