N-stearoyl-L-tryptophan | 21400-91-9

• 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: N-stearoyl-L-tryptophan
• 英文别名: N-n-octadecanoyl (L)-tryptophan；stearic-Trp-OH；N-stearoyltryptophan；N-stearoyl tryptophan；(2S)-3-(1H-indol-3-yl)-2-(octadecanoylamino)propanoic acid
• CAS: 21400-91-9
• 化学式: C₂₉H₄₆N₂O₃
• 分子量: 470.696
• InChiKey: QZMGCBALCCFOPR-MHZLTWQESA-N

物化性质

• 熔点：
  95-97 °C
• 沸点：
  677.4±50.0 °C(Predicted)
• 密度：
  1.047±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9
• 重原子数：
  34
• 可旋转键数：
  20
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.66
• 拓扑面积：
  82.2
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  L-色氨酸甲酯盐酸盐 在 sodium hydroxide 、 potassium hydrogencarbonate 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 氯仿 、 水 为溶剂， 反应 7.0h， 生成 N-stearoyl-L-tryptophan
  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

• Synthesis of Lipoamino Acids and Their Activity against Cerebral Ischemic Injury
  作者：Li-Yun Yao、Qi Lin、Yin-Yao Niu、Ke-Min Deng、Jian-Hua Zhang、Yang Lu

  DOI：10.3390/molecules14104051

  日期：——

  A series of lipoamino acids were synthesized and their neuroprotective effect against brain ischemia induced by oxygen-glucose deprivation (OGD) on rat cerebral slices was evaluated. Among these compounds, N-stearoyl-L-tyrosine (4), N-stearoyl-L-serine (5) and N-stearoyl-L-threonine (6) exhibited good neuroprotective activity. We found that the neuroprotective activity of lipoamino acids depended on the acyl group, the presence of a free carboxylic function and a free hydroxyl group at the branched chain of the amino acids. The results also showed that 5 was the most active compound, protecting rat brain slices against OGD as well as hydrogen peroxide (H2O2) insult at the range of 1–10 M.

  一系列脂氨基酸被合成，并评估了它们对大鼠脑片由氧葡萄糖剥夺（OGD）诱导的脑缺血的神经保护作用。在这些化合物中，N-硬脂酰基-L-酪氨酸（4）、N-硬脂酰基-L-丝氨酸（5）和N-硬脂酰基-L-苏氨酸（6）表现出了良好的神经保护活性。我们发现，脂氨基酸的神经保护活性依赖于酰基团、氨基酸支链上自由羧基和自由羟基的存在。结果还显示，5是最活跃的化合物，在1-10 M的范围内保护大鼠脑片免受OGD和过氧化氢（H2O2）的损伤。
• In Situ Synthesis of Gold and Silver Nanoparticles by Using Redox-Active Amphiphiles and Their Phase Transfer to Organic Solvents
  作者：Satyabrata Si、Enakshi Dinda、Tarun K. Mandal

  DOI：10.1002/chem.200701014

  日期：——

  An in situ reduction approach to synthesizing gold and silver nanoparticles by using a series of newly designed, redox-active amphiphiles at basic pH is described. These amphiphiles are the conjugates of a fatty acid (e.g., oleic acid, stearic acid, and lauric acid) and a redox-active amino acid (e.g., tryptophan or tyrosine). The amphiphile-coated nanoparticles are then efficiently transferred from

  描述了一种通过在碱性pH下使用一系列新设计的氧化还原活性两亲物来原位合成金和银纳米粒子的方法。这些两亲物是脂肪酸（例如油酸，硬脂酸和月桂酸）和氧化还原活性氨基酸（例如色氨酸或酪氨酸）的缀合物。然后，仅通过酸处理就可以将两亲涂层纳米颗粒从水中有效转移到不同的非极性有机介质（例如苯，甲苯，二甲苯，环己烷和己烷）中。通过紫外/可见光谱和透射电子显微镜监测相转移过程，结果表明，转移到有机介质后，平均粒径和粒径分布几乎保持不变。通过FTIR光谱和热重分析证实了两亲物对纳米颗粒表面的锚定。提出了一种机制来描述原位形成的胶态金纳米粒子和银纳米粒子的稳定性以及它们向有机溶剂中的相转移。两亲物的存在增加了胶体金纳米颗粒共轭物在有机溶剂中的热稳定性。
• COMPOSITION FOR TREATING ATOPY OR PRURITUS COMPRISING N-ACETYL OR N-ACYL AMINO ACID
  申请人：Stemdr Inc.

  公开号：EP3714880A2

  公开（公告）日：2020-09-30

  The present disclosure relates to a composition for preventing, alleviating or treating pruritus and/or atopy using an N-acetylamino acid or an N-acylamino acid having almost no side effects on the human body. Also, the present disclosure relates to a cosmetic composition for moisturizing skin or soothing skin. The composition of the present disclosure may be utilized to ameliorate a problematic skin condition caused by various causes, or to safely and effectively alleviate or treat pruritus and/or atopy without concern about side effects.

  本公开涉及一种使用对人体几乎无副作用的 N-乙酰基氨基酸或 N-酰基氨基酸来预防、减轻或治疗皮肤瘙痒症和/或过敏症的组合物。此外，本公开还涉及一种用于滋润皮肤或舒缓皮肤的化妆品组合物。本公开的组合物可用于改善由各种原因引起的皮肤问题，或安全有效地缓解或治疗皮肤瘙痒症和/或过敏症，而无需担心副作用。
• Higher N-acyl-L-amino acid derivatives
  作者：K. A. Kochetkov、Zh. S. Urmambetova、V. M. Belikov、Z. B. Bakasova

  DOI：10.1007/bf00958844

  日期：1990.11

  A preparative method is proposed for obtaining higher N-acylamino acids by reaction of free amino acids with fatty acid nitrophenyl esters. It was shown that these acids can transport positive ions through a liquid lipophilic medium. A direct method is proposed for obtaining fatty acid 4-nitrophenyl esters by boiling 4-nitrophenol and the fatty acid in xylene in a Soxhlet apparatus in the presence of an acid catalyst.
• Preparation, characterization, and surface and biological properties of<i>N</i>-stearoyl amino acids
  作者：A. Sivasamy、M. Krishnaveni、P. G. Rao

  DOI：10.1007/s11746-001-0361-5

  日期：2001.9

  AbstractSeveral lipoamino acids were synthesized, in which n‐octadecanoic acid (stearic acid) was coupled with the α‐amino group of an amino acid. The products were characterized and their identities confirmed by advanced analytical techniques like Fourier transform infrared 1H nuclear magnentic resonance spectroscopy, and differential scanning, calorimetry. Their surface properties, such as critical micelle concentration (CMC) and foaming properties, biodegradability, and antimicrobial activity were also evaluated. The N‐stearoyl amino acids (NSA) had low CMC values, and some of them showed good foaming properties. They were screened for antimicrobial activity against the gram‐positive bacteria Staphylococcus aureus, Micrococcus luteus, and Bacillus cerceus, the gram‐negative bacteria Escherichia coli and Pseudomonas aeruginosa, and the yeast Candida albicans. All the compounds inhibited at least one of these organisms. N‐Stearoyl proline was the most effective, the order of antimicrobial activity being aromatic NSA> acidic NSA>basic NSA. However, the effective inhibition by all the compounds indicates the desirability of more thorough investigation and suggests that some of these compounds may have potential utility as biostatic additives in commercial products. All NSA are highly biodegradable and can readily be removed under conditions of normal secondary sewage treatment.