12-acryloyloxy-1-dodecanoic acid | 99743-69-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 12-acryloyloxy-1-dodecanoic acid
• 英文别名: 12-acryloyloxydodecanoic acid；12-(Acryloyloxy)dodecanoic acid；12-prop-2-enoyloxydodecanoic acid
• CAS: 99743-69-8
• 化学式: C₁₅H₂₆O₄
• 分子量: 270.369
• InChiKey: UMCCUWIOCGWHRP-UHFFFAOYSA-N

物化性质

• 沸点：
  392.2±15.0 °C(Predicted)
• 密度：
  1.003±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  19
• 可旋转键数：
  14
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  12-acryloyloxy-1-dodecanoic acid 在 4-二甲氨基吡啶 、 2,6-二叔丁基-4-甲基苯酚 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 氯仿 为溶剂， 反应 68.0h， 生成 1-O-palmitoyl-2-O-(12-acryloyloxy)dodecanoyl-sn-glycero-3-phosphoethanolamine
  参考文献：
  名称：

  A facile synthesis of bifunctional phospholipids for biomimetic membrane engineering

  摘要：

  We report a facile synthesis of bifunctional phospholipid conjugates by acylation of N-protected lyso-phosphatidylethanolamine with 12-acryloxy-1-dodecanoic acid and followed with deprotection and conjugation with biotin, FITC, Texas Red, or EMC groups. The lipid conjugates can be used to generate a multifunctional substrate-supported phospholipid membrane via bioconjugation reaction to biotin or covalent attachment to EMC at their hydrophilic terminus. In addition, conjugation to fluorophores, FITC or Texas Red, provides a convenient mechanism to monitor lipid membrane formation and stability. Significantly, in situ photopolymerization of the acrylate group at the end of one of two hydrophobic alkyl chains stabilizes the phospholipid membrane. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.09.110
• 作为产物：
  描述：

  12-羟基十二酸 、 丙烯酰氯 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 生成 12-acryloyloxy-1-dodecanoic acid
  参考文献：
  名称：

  Effect of Hydrophobic Side Chain on Poly(carboxyl acid) Dissociation and Surfactant Binding

  摘要：

  Copolymers consisting of acrylic acid (AA) and 12-acryloyldodecanoic acid (ADA) [poly(ADA-co-AA)] were synthesized, and their dissociation behaviors and binding characteristics with ionic surfactant, dodecylpyridinium. chloride, were investigated. The dissociation is strongly suppressed in the presence of ADA, and when the ADA molar fraction (F-ADA) is 0.5, the copolymer exhibits a distinct two-stage dissociation associated with AA and ADA. The binding process is also changed by the presence of ADA. When the ADA content is low, the surfactants bind cooperatively to form a stoichiometric complex. An increase in ADA content brings about noncooperative and nonstoichiometric complexion. The initiation constant (K-0) for an isolated surfactant binding to poly(ADA(F-ADA = 1.0)) is more than 3 orders of magnitude larger than that of poly(AA(FADA = 0)), indicating that the initiation of the binding is associated not only with the electrostatic interaction but also with the hydrophobic interaction between the alkyl chains of surfactant and ADA. The structure of surfactant-poly(ADA-co-AA) complexes changes from micelle-like to lamellar-like with the increase in F-ADA.

  DOI：

  10.1021/ma0351470

文献信息

• Contrast agents
  申请人：Nycomed Imaging AS

  公开号：US05536490A1

  公开（公告）日：1996-07-16

  The invention relates to diagnostic ultrasound contrast agents comprising vesicles comprising an amphiphilic phospholipid material capable of formation of gas-containing vesicles wherein the vesicles contain gas which comprises sulphur hexafluoride. The contrast agents and vesicles exhibit good stability in vivo upon administration and may if desired incorporate biodegradable linkages so as to possess particularly desired levels of biodegradability.

  该发明涉及包含能够形成含气囊的囊泡的含有两性磷脂材料的诊断超声造影剂，其中囊泡含有含有六氟化硫的气体。这些造影剂和囊泡在体内给药后表现出良好的稳定性，如有需要，可以包含可生物降解的连接以具有特定所需的生物降解水平。
• Microbubble-containing contrast agents having a non-proteinaceous
  申请人：Nycomed Imaging AS

  公开号：US06106806A1

  公开（公告）日：2000-08-22

  Ultrasound contrast agents having microbubbles of gas or a gas precursor encapsulated by non-proteinaceous crosslinked or polymerised amphiphilic moieties, e.g. in the form of micelles, exhibit good stability in vivo upon administration and may if desired incorporate biodegradable linkages so as to possess particular desired levels of biodegradability.

  超声造影剂具有气泡或气体前体微囊，其被非蛋白交联或聚合的两性分子封装，例如以胶束形式，体内给药后表现出良好的稳定性，并且如有需要可以包含可生物降解的连接，以具有特定所需的生物降解水平。
• Flexible amphiphilic microbubbles for ultrasound
  申请人：Nycomed Imaging AS

  公开号：US05567413A1

  公开（公告）日：1996-10-22

  The invention relates to diagnostic ultrasound contrast agents comprising vesicles comprising an amphiphilic phospholipid material capable of formation of gas-containing vesicles wherein the vesicles contain gas which comprises a low molecular weight fluorinated hydrocarbon.

  本发明涉及诊断超声造影剂，其包括含有两亲性磷脂材料的囊泡，能够形成含气囊泡，其中囊泡含有气体，该气体包含低分子量氟化碳氢化合物。
• Modular cytomimetic biomaterials, transport studies, preparation and utilization thereof
  申请人：Emory University

  公开号：US20030216534A1

  公开（公告）日：2003-11-20

  A modular cytomimetic biocompatible biomaterial, comprising a phospholipid or phospholipid derivative comprising various functional groups (e.g., lipid, peptide, sugar) having specific chemical properties which can function as a modular surface design unit to be incorporated or appended to a desired substrate (e.g., a polymer or a metal) on which it is then polymerized in situ, thereby contributing new or specified biochemical characteristics to the polymerized and stabilized biomaterial.

  一种模块化仿细胞生物相容性生物材料，由磷脂或磷脂衍生物组成，磷脂或磷脂衍生物含有各种官能团（如脂质、肽、糖），具有特定的化学性质，可作为模块化表面设计单元与所需基质（如聚合物或金属）结合或附着，然后在基质上就地聚合，从而为聚合和稳定的生物材料提供新的或特定的生物化学特性。
• Antithrombogenic membrane mimetic compositions and methods
  申请人：——

  公开号：US20040073295A1

  公开（公告）日：2004-04-15

  The present Specification describes materials and methods which provide for improved performance of medical prostheses, including vascular graft material, artificial heart valves, and other implanted materials. The materials comprising bound thrombomodulin or a functionally equivalent derivative protein, provide for fewer undesirable side effects including inflammation, thromboses and neointimal hyperplasia.

  本说明书描述的材料和方法可改善医疗假体的性能，包括血管移植材料、人工心脏瓣膜和其他植入材料。包含结合血栓调节蛋白或功能相当的衍生物蛋白的材料可减少不良副作用，包括炎症、血栓形成和新内膜增生。