N-hexadecanoyl-L-aspartic acid | 1782-17-8

• 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-hexadecanoyl-L-aspartic acid
• 英文别名: N-Palmitoyl-L-asparginsaeure；N-palmitoyl-L-aspartic acid；N-palmitoyl aspartic acid；Palmitoyl-L-aspartic acid；(2S)-2-(hexadecanoylamino)butanedioic acid
• CAS: 1782-17-8
• 化学式: C₂₀H₃₇NO₅
• 分子量: 371.517
• InChiKey: ZYJZBFYRVKLOAA-KRWDZBQOSA-N

物化性质

• 熔点：
  121-122.5 °C
• 沸点：
  539.5±40.0 °C(Predicted)
• 密度：
  1.048±0.06 g/cm3(Predicted)
• 溶解度：
  DMF：20mg/mL； DMSO：15mg/mL；乙醇：25mg/mL；乙酸甲酯：10mg/mL； PBS（pH 7.2）：2 mg/mL

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  26
• 可旋转键数：
  18
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  104
• 氢给体数：
  3
• 氢受体数：
  5

制备方法与用途

Palmitoyl-L-aspartic acid is a natural N-acylaspartate that inhibits Hedgehog signaling following stimulation with Smoothened agonist or non-sterol-modified Sonic Hedgehog. It does not affect the activity of cannabinoid receptors or fatty acid amide hydrolase.

反应信息

• 作为产物：
  描述：

  棕榈酸 在 magnesium sulfate 、 对甲苯磺酸 、 三乙胺 作用下， 以 1,4-二氧六环 、 水 、 xylene 为溶剂， 反应 9.0h， 生成 N-hexadecanoyl-L-aspartic acid
  参考文献：
  名称：

  Higher N-acyl-L-amino acid derivatives

  摘要：

  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.

  DOI：

  10.1007/bf00958844

文献信息

• Process for preparing N-higher aliphatic acyl derivatives of amino
  申请人：Ajinomoto Co., Inc.

  公开号：US03985722A1

  公开（公告）日：1976-10-12

  A mixed acid anhydride consisting of higher fatty acid having 6 to 22 carbon atoms and sulfuric anhydride is reacted with amino acids, peptides or proteins in the presence of a base to form N-higher aliphatic acyl derivatives of amino acids, peptides or proteins respectively in good yield. The reaction mixture comprises N-acylated-amino acids, peptides or -proteins and sulfate salts and may be directly used as detergent.

  一种混合酸酐，由具有6到22个碳原子的高级脂肪酸和硫酸酐组成，与氨基酸、肽或蛋白质在碱的存在下反应，以形成氨基酸、肽或蛋白质的N-高级脂肪酰衍生物，收率良好。反应混合物包括N-酰化氨基酸、肽或蛋白质和硫酸盐，可以直接用作洗涤剂。
• Fatty Acid Acylated D-Amino Acids for Oral Peptide Delivery
  申请人：Novo Nordisk A/S

  公开号：US20150265710A1

  公开（公告）日：2015-09-24

  The present invention relates to fatty acid acylated amino acids (FA-Daa's) acting as permeation enhancers for oral delivery of therapeutic macromolecules such as peptides and pharmaceutical compositions comprising such FA-Daa's.

  本发明涉及脂肪酸酰化氨基酸（FA-Daa），其作为渗透增强剂用于口服治疗大分子药物，如肽类，并包括含有这些FA-Daa的制药组合物。
• Process for producing polymer particles
  申请人：KAO CORPORATION

  公开号：EP0733648A1

  公开（公告）日：1996-09-25

  A process for producing polymer particles comprising polymerizing a water-soluble polymerizable monomer in a system comprising a hydrophobic organic solvent inert to the polymerization and an aqueous solution of the water-soluble polymerizable monomer, the process being characterized in that the polymerization is carried out in the presence of, as a dispersant, an anionic surface active agent represented by formula (I): wherein R1 represents a straight-chain or branched alkyl, alkenyl or 2-hydroxyalkyl group having 5 to 29 carbon atoms; M1 and M2, which may be the same or different, each represent an alkali metal ion, an ammonium ion or a hydrogen atom; and n represents 1 or 2.

  一种生产聚合物颗粒的工艺，包括在由惰性于聚合的疏水性有机溶剂和水溶性可聚合单体的水溶液组成的体系中聚合水溶性可聚合单体，该工艺的特征在于聚合是在由式(I)代表的阴离子表面活性剂作为分散剂存在的情况下进行的： 其中 R1 代表具有 5 至 29 个碳原子的直链或支链烷基、烯基或 2-羟基烷基；M1 和 M2 可以相同或不同，各自代表碱金属离子、铵离子或氢原子；n 代表 1 或 2。
• O/W/O TYPE MULTIPHASE EMULSION
  申请人：SHISEIDO COMPANY LIMITED

  公开号：EP0970741A1

  公开（公告）日：2000-01-12

  An O/W/O type multiple emulsion in which an O/W type emulsion is dispersed in the outer phase oil wherein the O/W type emulsion in the inner phase contains water, an oil based ingredient, a surfactant and an amphiphilic substance chosen from those which can form a gel at ordinal temperature or higher in an amphiphilic substance-surfactant-oil-water system or N-long chain acyl acidic amino acid monosalt and an amphiphilic substance chosen from those which can form a gel at ordinal temperature or higher in an amphiphilic substance-N-long chain acyl acidic amino acid monosalt-oil-water system, said outer phase oil contains organophilic modified clay minerals and an emulsifying agent with a HLB of 7 or lower, and the weight ratio of the O/W type emulsion and the outer phase oil is 2 : 3 - 19 : 1. An O/W/O type multiple emulsion with superior stability over time and good usability.

  一种 O/W/O 型多元乳液，其中 O/W 型乳液分散在外相油中，而内相中的 O/W 型乳液含有水、油基成分、表面活性剂和一种两亲物质，选自两亲物质-表面活性剂-油-水体系中在常温或更高温度下可形成凝胶的物质，或 N-长链酰基酸性氨基酸单唾液酸和一种两亲物质，选自两亲物质-N-长链酰基酸性氨基酸单唾液酸-油-水体系中在常温或更高温度下可形成凝胶的物质、所述外相油含有亲有机改性粘土矿物和 HLB 为 7 或更低的乳化剂，且 O/W 型乳液和外相油的重量比为 2 ：3 - 19 : 1.O/W/O 型复配乳液具有卓越的长期稳定性和良好的可用性。
• Skin model
  申请人：Symrise GmbH & Co. KG

  公开号：EP1927656A1

  公开（公告）日：2008-06-04

  The present invention relates to the use of a pig skin sample as a skin model, particularly for the assessment of pharmacological and cosmetic effects.

  本发明涉及使用猪皮肤样本作为皮肤模型，特别是用于评估药理和美容效果。