rac-1,2-di-O-octadecylglycerol | 6076-38-6

• 物质功能分类: 有机原料 - 醇、酚、酚醇类化合物及衍生物
• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 甘油脂
• 英文名称: rac-1,2-di-O-octadecylglycerol
• 英文别名: 2,3-Bis(octadecyloxy)propan-1-ol；2,3-dioctadecoxypropan-1-ol
• CAS: 6076-38-6
• 化学式: C₃₉H₈₀O₃
• 分子量: 597.062
• InChiKey: QEHCYTDFERPPPU-UHFFFAOYSA-N

物化性质

• 熔点：
  64～65
• 沸点：
  653.6±35.0 °C(Predicted)
• 密度：
  0.874±0.06 g/cm3(Predicted)
• 溶解度：
  DMF：20mg/mL； DMSO：5mg/mL；乙醇：30mg/mL； PBS（pH 7.2）：0.25 mg/mL

计算性质

• 辛醇/水分配系数(LogP)：
  17
• 重原子数：
  42
• 可旋转键数：
  38
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2909499000

反应信息

• 作为反应物：
  描述：

  rac-1,2-di-O-octadecylglycerol 在 甲醇 、 氨 、 碘 、 sodium methylate 、 四丁基硫酸氢铵 、 silver carbonate 、 sodium hydroxide 、 silver(l) oxide 作用下， 以 氯仿 、 水 、 甲苯 为溶剂， 13.0~50.0 ℃ 、1.0 MPa 条件下， 反应 92.0h， 生成 6-desoxy-6-amino-1-O-(2,3-bis(octadecyloxy)propyl)-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of novel amphiphilic conjugates with a biological recognition function for developing targeted triggered liposomal delivery systems

  摘要：

  Several novel amphiphilic lipid derivatives were synthesized consisting of a lipid anchor connected to the hydrophilic moiety via a disulfide or glycoside bond and biotin linked to the hydrophilic part. Disulfide bonds were established by the help of 4-phenyltriazol-3,5-dione. Dansyl or fluorescein was covalently linked as fluorescent marker to some of the conjugates, allowing spectroscopic and microscopic detection. The conjugates represent first amphiphilic lipids carrying all four functions, i.e., lipophilic, hydrophilic, recognition, and disulfide cleavage group in one molecule, which are necessary for targeted, triggered drug delivery from phospholipid liposomes on demand. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.07.089
• 作为产物：
  描述：

  鲨肝醇 在 吡啶 作用下， 生成 rac-1,2-di-O-octadecylglycerol
  参考文献：
  名称：

  Reactions of Aliphatic Methanesulfonates. II. Syntheses of Long-Chain Di- and Trialkyl Glyceryl Ethers¹

  摘要：

  DOI：

  10.1021/jo01340a034

文献信息

• Langmuir–Blodgett film formation of succinic acid half-esters containing double long alkoxy chains
  作者：Shuichi Osanai、Makoto Higami、Yuko Ono、Eiji Ohta

  DOI：10.1039/a700716g

  日期：——

  Two types of half-esters of succinic acid have been prepared. One contains a 1,2-dialkylated glyceryl group, while the other has a normal alkyl group as the hydrophobic group. The mono-molecular films of the half-esters developed at the air–water interface were evaluated byπ–A curves. Multilayer Langmuir–Blodgett (L–B) films deposited on the substrate are discussed in terms of pinhole defects. Influences of the surface pressure on accumulation, the number of layers, and the chain length of the lipophilic group are analysed. The L–B film made from the double-chained homologues possessed fewer pinhole defects compared with that composed of the single-chained one.

  已制备了两种丁二酸半酯类型。一种包含1,2-二烷基化的甘油基团，而另一种则具有正常的烷基作为疏水基团。通过π-A曲线评估了这些半酯在气-水界面上形成的单分子膜。关于基板上的多层Langmuir-Blodgett（L-B）膜，就其针孔缺陷进行了讨论。分析了表面压力对累积、层数和亲脂性基团链长的影响。由双链同系物制备的L-B膜相比于单链同系物制备的膜具有更少的针孔缺陷。
• Self-organization of polymeric lipids with hydrophilic spacers in side groups and main chain: investigation in monolayers and multilayers
  作者：A. Laschewsky、H. Ringsdorf、G. Schmidt、J. Schneider

  DOI：10.1021/ja00237a025

  日期：1987.2

  Several polymerizable lipids were synthesized and polymerized to amphiphilic homopolymers and to copolymers with the help of hydrophilic comonomers. The self-organization of these polymeric lipids was investigated in monolayers and Langmuir-Blodgett multilayers. The self-organization of these polymers in model membranes is due to hydrophilic spacer groups in the amphiphilic side groups as well as to

  在亲水共聚单体的帮助下，几种可聚合的脂质被合成并聚合成两亲性均聚物和共聚物。在单层和 Langmuir-Blodgett 多层中研究了这些聚合物脂质的自组织。这些聚合物在模型膜中的自组织是由于两亲侧基中的亲水间隔基团以及聚合物主链中的亲水间隔基团。因此，很容易获得高度有序的单层和 LB 多层。Scheme I. 含亲水间隔基团的两亲聚合物示意图"
• [EN] TREATING EPHRIN RECEPTOR A2 (EPHA2) POSITIVE CANCER WITH TARGETED DOCETAXEL-GENERATING NANO-LIPOSOME COMPOSITIONS<br/>[FR] TRAITEMENT DU CANCER POSITIF AU RÉCEPTEUR DE L'ÉPHRINE A2 (EPHA2) AVEC DES COMPOSITIONS DE NANOLIPOSOMES CIBLÉS DE GÉNÉRATION DE DOCÉTAXEL
  申请人：MERRIMACK PHARMACEUTICALS INC

  公开号：WO2017161071A1

  公开（公告）日：2017-09-21

  EphA2 targeted doxorubicin generating nano-liposomes are useful in the treatment of cancer overexpressing EphA2, alone or in combination with chemotherapeutic agents such as gemcitabine or carboplatin.

  EphA2靶向阿霉素生成的纳米脂质体在治疗过表达EphA2的癌症方面非常有用，可以单独使用，也可以与吉西他滨或卡铂等化疗药物联合使用。
• Synthesis of Nucleosides with 2′-Fixed Lipid Anchors and Their Behavior in Phospholipid Membranes
  作者：Oliver Kaczmarek、Nicolai Brodersen、Andreas Bunge、Ludwig Löser、Daniel Huster、Andreas Herrmann、Anna Arbuzova、Jürgen Liebscher

  DOI：10.1002/ejoc.200701064

  日期：2008.4

  Various new nucleosides bearing one or two lipophilic groups at the 2′-position have been synthesized. The lipophilic substituents were attached to a 2′-hydroxy, 2′-amino, or 2′-thio function. These lipophilic nucleosides anchor in large unilamellar POPC vesicles serving as phospholipid membrane models. The insertion of these molecules into the membranes was investigated by NMR techniques. For comparison

  已经合成了各种在 2' 位带有一个或两个亲脂基团的新核苷。亲脂性取代基连接到 2'-羟基、2'-氨基或 2'-硫代官能团。这些亲脂性核苷锚定在用作磷脂膜模型的大型单层 POPC 囊泡中。通过核磁共振技术研究了这些分子插入到膜中的情况。为了进行比较，还研究了在 2'-、3'-或 5'-位置具有两个或三个亲脂基团的核苷。（© Wiley-VCH Verlag GmbH & Co. KGaA，69451 Weinheim，德国，2008 年）
• COSMETIC COMPOSITION COMPRISING AT LEAST ONE CATIONIC COPOLYMER AND AT LEAST ONE ANIONIC ASSOCIATIVE POLYMER AND COSMETIC TREATMENT PROCESSES USING SAID COMPOSITION
  申请人：BIGANSKA Olga

  公开号：US20090074692A1

  公开（公告）日：2009-03-19

  The disclosure relates to novel cosmetic compositions comprising, in a cosmetically acceptable medium: (i) at least one cationic polymer which are produced by polymerization of a mixture of monomers comprising: a) at least one vinyl monomer substituted with at least one amino group, b) at least one hydrophobic nonionic vinyl monomer, c) at least one associative vinyl monomer, and e) at least one hydroxylated nonionic vinyl monomer, and (ii) at least one anionic associative polymers.

  该披露涉及新型化妆品组合物，包括在适合用于化妆的介质中的：(i) 至少一种阳离子聚合物，其由包括：a) 至少一种含有至少一个氨基团的乙烯单体，b) 至少一种疏水非离子乙烯单体，c) 至少一种关联性乙烯单体，和e) 至少一种羟基化非离子乙烯单体的单体混合物聚合而成，以及(ii) 至少一种阴离子关联性聚合物。