二癸酸甘油酯 | 53988-07-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 甘油脂
• 中文名称: 二癸酸甘油酯
• 英文名称: 1, 3-dicaprin
• 英文别名: 1,3-bisdecanoyl glycerol；1,3-didecanoylglycerol；(3-decanoyloxy-2-hydroxypropyl) decanoate
• CAS: 53988-07-1
• 化学式: C₂₃H₄₄O₅
• 分子量: 400.599
• InChiKey: BPYWNJQNVNYQSQ-UHFFFAOYSA-N

物化性质

• 溶解度：
  DMF：20 mg/ml； DMSO：5 mg/ml；乙醇：30 mg/ml； PBS（pH 7.2）：250 μg/ml
• 物理描述：
  Solid
• 保留指数：
  2774.1

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  28
• 可旋转键数：
  22
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.913
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  二癸酸甘油酯 在 吡啶 作用下， 以 乙醚 、 氯仿 、 异丙醇 、 乙腈 为溶剂， 反应 1.0h， 生成 1,3-didecanoylglycero-2-phosphocholine
  参考文献：
  名称：

  1,3-Diacylglycero-2-phosphocholines — synthesis, aggregation behaviour and properties as inhibitors of phospholipase D

  摘要：

  A series of 1,3-diacylglycero-2-phosphocholines (1,3-PCs) with acyl chain lengths of C-8-C-18 were synthesised by chemical introduction of the phosphocholine moiety into the regioisomerically pure 1,3-diacylglycerols, which were obtained from glycerol and the vinyl esters of fatty acid by means of lipase from Rhizomucor mihei. The I,3-PCs being regioisomers of the natural glycerophospholipids were studied with respect to their aggregation behaviour in the absence and in the presence of sodium dodecylsulfate (SDS) as well as their properties as substrates and inhibitors of phospholipase D (PLD) from cabbage. While the main structures of the pure 1,3-PCs were micelles (C-8), liposomes (C-10, C-12) or planar bilayers (C-14, C-16, C-18), the addition of SDS resulted in the formation of mixed micelles (C-8, C-10) and mixed liposomes (C-12, C-14, C-16, C-18). None of the 1,3-PCs was found to be hydrolysed by PLD, whereas all of them showed inhibitory properties in the standard assay for PLD. The inhibitory power was strongest with 1,3-didecanoylglycero-2-phosphocholine (IC50 = 43 mu M). (C) Elsevier Science Ireland Ltd. All rights reserved.

  DOI：

  10.1016/s0009-3084(99)00120-6
• 作为产物：
  描述：

  1,3-dicaproyloxypropan-2-one 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 0.33h， 以82%的产率得到二癸酸甘油酯
  参考文献：
  名称：

  选择性氘代技术，可帮助您深入了解中链甘油三酸酯的消化过程

  摘要：

  中链甘油三酸酯（MCT）是一种独特的膳食脂肪，具有广泛的健康益处。它们是带有甘油骨架的分子，该骨架在两个外部位置（sn-1和sn-3）和中间位置（sn-2）被中链（6-12个碳原子）脂肪酸酯化。在胃肠道中的脂质消化过程中，胰腺脂肪酶立体选择性地水解这些甘油三酸酯在sn-1和sn-3位置上的酯键，从而导致sn-2单甘油酯和脂肪酸为主要产物。但是，sn-2甘油单酸酯的热力学稳定性低于其sn-1 / 3同行。从sn-2单酸甘油酯到sn-1 / 3单酸甘油酯的异构化或脂肪酸迁移可能会自发发生，并会导致甘油和脂肪酸作为最终产物。在这里，具有选择性氘代脂肪酸链的三癸酸酯（C10）首次用于监测链迁移和胰脂肪酶催化的酯键水解的立体选择性。在生物相关条件下，使用NMR和质谱法研究了中间和最终消化产物。sn-2的水解由于在消化培养基中长期存在未消化的甘油二酯类物质，因此在生物学相关的时间范围内未发生单癸酸酯向

  DOI：

  10.1016/j.chemphyslip.2015.06.007

文献信息

• [EN] LYMPHATIC SYSTEM-DIRECTING LIPID PRODRUGS<br/>[FR] PROMÉDICAMENTS LIPIDIQUES ORIENTANT VERS LE SYSTÈME LYMPHATIQUE
  申请人：ARIYA THERAPEUTICS INC

  公开号：WO2019046491A1

  公开（公告）日：2019-03-07

  The present invention provides lymphatic system-directing lipid prodrugs, pharmaceutical compositions thereof, methods of producing such prodrugs and compositions, as well as methods of improving the bioavailability or other properties of a therapeutic agent that comprises part of the lipid prodrug. The present invention also provides methods of treating a disease, disorder, or condition such as those disclosed herein, comprising administering to a patient in need thereof a provided lipid prodrug or a pharmaceutical composition thereof.

  本发明提供了淋巴系统定向脂质前药，其制药组合物，制备这种前药和组合物的方法，以及改善作为脂质前药一部分的治疗剂的生物利用度或其他性质的方法。本发明还提供了治疗疾病、紊乱或症状的方法，包括向需要的患者施用所提供的脂质前药或其制药组合物。
• [EN] LIPID PRODRUGS OF JAK INHIBITORS AND USES THEREOF<br/>[FR] PROMÉDICAMENTS LIPIDIQUES D'INHIBITEURS DE JAK ET LEURS UTILISATIONS
  申请人：PURETECH LYT INC

  公开号：WO2020176859A1

  公开（公告）日：2020-09-03

  The present invention provides lymphatic system-directing lipid prodrugs, pharmaceutical compositions thereof, methods of producing such prodrugs and compositions, and methods of improving the bioavailability or other properties of a therapeutic agent that comprises part of the lipid prodrug. The present invention also provides methods of treating a disease, disorder, or condition such as those disclosed herein, comprising administering to a patient in need thereof a disclosed lipid prodrug or a pharmaceutical composition thereof.

  本发明提供了淋巴系统定向脂质前药，其药物组成物，生产这种前药和组成物的方法，以及改善作为脂质前药一部分的治疗剂的生物利用度或其他性质的方法。本发明还提供了治疗疾病、紊乱或状况的方法，例如本文所披露的那些，包括向需要的患者施用所披露的脂质前药或其药物组成物。
• [EN] TREATMENT OF NEURODEGENERATIVE CONDITIONS<br/>[FR] TRAITEMENT D'ETATS NEURODEGENERATIFS
  申请人：BTG INT LTD

  公开号：WO2005018632A1

  公开（公告）日：2005-03-03

  A method is provided for treating a patient in need of therapy for a neurodegenerative disease comprising administering to that patient a therapeutically effective dose of a lipid glyceride comprising a glycerol moiety and a fatty acid moiety, the fatty acid moiety being selected from the group consisting of Ϝ-linolenic acid, dihomo-Ϝ-linolenic acid and arachidonic acid characterised in that the selected fatty acid moiety is attached to the glycerol moiety at its sn-2 position. Preferably the method is that wherein the lipid is administered for a duration and at a dose sufficient to maintain or elevate TGF-β1 levels in the patient to therapeutic levels.

  提供了一种治疗神经退行性疾病患者的方法，包括向该患者施用含有甘油基团和脂肪酸基团的治疗有效剂量的脂质甘油酯，所述脂肪酸基团选自Ϝ-亚麻酸、二油酸和花生四烯酸组成的群体，其特点在于所选的脂肪酸基团附着在甘油基团的sn-2位置。最好的方法是，脂质被施用的持续时间和剂量足以维持或提高患者体内TGF-β1水平至治疗水平。
• Diaryldiazepine Prodrugs for the Treatment of Neurological and Psychological Disorders
  申请人：Remenar Julius F.

  公开号：US20110166128A1

  公开（公告）日：2011-07-07

  The present invention provides prodrug compounds of diaryldiazepine drug compounds.

  本发明提供了二苯并二氮杂苯类药物化合物的前药化合物。
• 1-O-Alkyl (di)glycerol ethers synthesis from methyl esters and triglycerides by two pathways: catalytic reductive alkylation and transesterification/reduction
  作者：Marc Sutter、Wissam Dayoub、Estelle Métay、Yann Raoul、Marc Lemaire

  DOI：10.1039/c3gc36907b

  日期：——

  esters, monoglycerides or oleic sunflower refined oil, the corresponding 1-O-alkyl (di)glycerol ethers were obtained in both high yields and selectivity by two different pathways. With methyl esters, a reductive alkylation with (di)glycerol was realized under 50 bar hydrogen pressure in the presence of 1 mol% of Pd/C and an acid co-catalyst. A second two step procedure was evaluated from methyl esters

  从可用的和生物来源的甲酯中， 甘油单酸酯或油酸向日葵精制油，通过两种不同途径以高收率和选择性获得了相应的1- O-烷基（二）甘油醚。对于甲酯，在1mol％的Pd / C和酸助催化剂的存在下，在50巴的氢气压力下，实现了与（二）甘油的还原性烷基化。从甲酯或三油精 包括第一次酯交换反应成相应的 甘油单酸酯与BaO / Al 2 O 3 催化剂，然后 减少在H 2压力下，用可循环利用的非均相催化体系Pd / C和Amberlyst 35合成所需的甘油单醚。另外，还提出了反应机理。