(Z,Z,E)-9,12,15-十八碳三烯酸 | 21661-08-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: (Z,Z,E)-9,12,15-十八碳三烯酸
• 英文名称: (9Z,12Z,15E)-octadeca-9,12,15-trienoic acid
• 英文别名: (9Z,12Z,15E)-octadecatrienoic acid；9Z,12Z,15E-octadecatrienoic acid；(9Z,12Z,15E)-linolenic acid
• CAS: 21661-08-5
• 化学式: C₁₈H₃₀O₂
• 分子量: 278.435
• InChiKey: DTOSIQBPPRVQHS-NSAMXNATSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  20
• 可旋转键数：
  13
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (8Z,11Z,14E)-1-cyanoheptadeca=8,11,14-triene 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 反应 7.0h， 生成 (Z,Z,E)-9,12,15-十八碳三烯酸
  参考文献：
  名称：

  Synthesis of (9Z,12Z,15E)- and (9E,12Z,15Z)-octadecatrienoic acids and their [1-14C]-radiolabelled analogs

  摘要：

  In order to study the effect of the double bonds geometry of linolenic acid (18:3 n-3) on its biological activities, (9Z,12Z,15E)- and (9E,12Z,15Z)-octadecatrienoic acids, found in many refined vegetable oils, were made by total synthesis. Synthesis of 18:3 Delta 9c, 12c, 15t involves a Wittig reaction between 3-(2-tetrahydropyranyloxy)-propylphosphonium salt and (E)-3-hexenal which gave (3Z,6E)-1-(2-tetrahydropyranyloxy)-nonadiene in 66% yield. The transformation of the ether function to a phosphonium salt, followed by a Wittig reaction with 8-(t-butyldimethylsilyloxy)-octanal afforded a C17 trienic ether. A one-carbon homologation of its corresponding bromide with potassium cyanide followed by hydrolysis in basic medium furnished 18:3 Delta 9c, 12c, 15t in high isomeric purity and high radiochemical purity for its [1-C-14]-labelled analog. In the synthesis of 18:3 Delta 9t, 12c, 15c, a Wittig reaction between (E)-6-(2-tetrahydropyranyloxy)-hex-3-enylphosphonium salt, obtained in three steps from 6-(2-tetrahydropyranyloxy)-hex-3-yn-l-ol and (Z)-3-hexenal afforded a C12 (E,Z,Z)-trienic ether. After a six-carbon homologation of this ether, in three steps, the resulting nitrile was hydrolyzed to (9E,12Z, 15Z)-octadecatrienoic acid (99% purity) (99% radiochemical purity of its [1-C-14]-labelled analog).

  DOI：

  10.1016/0009-3084(94)90058-2

文献信息

• BIOACTIVE AGENT COATED MEDICAL DEVICE AND METHOD OF COATING SUCH A DEVICE
  申请人：Cook Medical Technologies LLC

  公开号：EP3659634A1

  公开（公告）日：2020-06-03

  A medical device such as a stent (10) or medical balloon (40) is functionalised prior to coating with a bioactive material (54), specifically by carboxylic acidification of the contact surface or surfaces (50) of the medical device. The preferred process involves washing a stent or other medical device in a washing solution which may be sodium hydroxide, soaking in a carboxylic acid solution, rinsing in water to remove excess carboxylic acid, allowing to dry before applying a bioactive agent layer. It has been found that washing after functionalisation removes excess carboxylic acid and enhances the retention of bioactive agent on the contact surface or surfaces of the medical device leading to a more uniform and consistent layer of bioactive agent.

  支架（10）或医用球囊（40）等医疗器械在涂覆生物活性材料（54）之前，特别是通过对医疗器械的一个或多个接触面（50）进行羧酸化处理，使其功能化。优选的工艺包括用氢氧化钠溶液清洗支架或其他医疗设备，浸泡在羧酸溶液中，用水冲洗以去除多余的羧酸，待其干燥后再涂上一层生物活性剂。研究发现，功能化后的水洗可以去除多余的羧酸，提高生物活性剂在医疗设备接触面上的保留率，使生物活性剂层更加均匀一致。
• Coated medical device and method of coating such a device
  申请人：Cook Medical Technologies LLC

  公开号：US10874772B2

  公开（公告）日：2020-12-29

  A medical device such as a stent (10) or medical balloon (40) is at least partially coated with a carboxylic acid layer in order to enhance biocompatibility, reduce thrombogenesis and increase endothelialisation. The coating is preferably of citric acid in non-crosslinked form and preferably non-porous so as to mask the underlying structure of the medical device. The acid coating forms an outer surface of at least a part of the medical device, that is has no other layer or material overlying it, save for in some embodiments a partial coating of a bioactive material.

  支架（10）或医用球囊（40）等医疗设备至少部分涂有羧酸层，以增强生物相容性、减少血栓形成和增加内皮化。涂层最好是非交联形式的柠檬酸，最好是无孔的，以便掩盖医疗设备的底层结构。酸涂层至少形成医疗设备一部分的外表面，其上没有其他层或材料，在某些实施例中，生物活性材料的部分涂层除外。
• MEAT PRODUCTS WITH INCREASED LEVELS OF BENEFICIAL FATTY ACIDS
  申请人：Monsanto Technology, LLC

  公开号：EP2230944A1

  公开（公告）日：2010-09-29
• POULTRY MEAT AND EGGS COMPRISING BENEFICIAL FATTY ACIDS
  申请人：Monsanto Technology LLC

  公开号：EP2408316A1

  公开（公告）日：2012-01-25
• POULTRY FEED COMPRISING BENEFICIAL FATTY ACIDS
  申请人：Monsanto Technology LLC

  公开号：EP2408316B1

  公开（公告）日：2017-01-04