3,6,9,12,15,18-docosahexaenoic acid

• 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: 3,6,9,12,15,18-docosahexaenoic acid
• 英文别名: (3Z,6Z,9Z,12Z,15Z,18Z)-docosa-3,6,9,12,15,18-hexaenoic acid
• 化学式: C₂₂H₃₂O₂
• 分子量: 328.495
• InChiKey: PBDDANQNUSTEJT-JDPCYWKWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  24
• 可旋转键数：
  14
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3,6,9,12,15,18-docosahexaenoic acid 生成 all-cis-3,6,8,12,15-octadecapentaenoic acid
  参考文献：
  名称：

  Toxic effects of Gymnodinium cf. mikimotoi unsaturated fatty acids to gametes and embryos of the sea urchin Paracentrotus lividus

  摘要：

  The toxicity of the main Gymnodinium cf. mikimotoi polyunsaturated fatty acid, has been investigated using the sea urchin gamete and embryo bioassays. The 18:5n3 Fatty acid delays or inhibits first cleavage of Paracentrotus lividus eggs and provokes abnormalities in the embryonic development. These effects were compared with those of other polyunsaturated fatty acids, 18:4n3, 20:5n3 and 22:6n3, which are also present in this al a. A classification of the different fatty acids, based on their effects on sea urchin egg cleavage and thee determination of the half inhibiting concentrations (IC(50)) is proposed. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0043-1354(99)00181-5

文献信息

• Practical Syntheses of Triacylglycerol Regioisomers Containing Long-chain Polyunsaturated Fatty Acids
  作者：Benjamin H. Fraser、Patrick Perlmutter、Chakra Wijesundera

  DOI：10.1007/s11746-006-1001-9

  日期：2007.1

  AbstractDocosahexaenoic acid (DHA, 22:6n‐3) is known to protect against a range of degenerative disease conditions and aid in the development of eye and brain function in infants. In dietary lipids DHA is found primarily in the triacylglycerol (TAG) form. However, the effects of the positional distribution of DHA in TAG on lipid functional properties such as bioactivity and oxidative stability are not clearly understood. Studies on this subject for the most part are limited by a lack of regioisomerically pure TAG model compounds containing DHA or similar long‐chain (LC)‐polyunsaturated fatty acids (PUFA). This paper reports on the development of a practical procedure, based on chemical and enzymatic reactions, for the syntheses of regioisomerically enriched, symmetrical and unsymmetrical TAG isomers containing two palmitic acid and one of linoleic acid, linolenic acid, or DHA. 1,3‐Selective acylation of glycerol with vinyl esters of fatty acids catalyzed by Candida antarctica lipase and direct coupling with fatty acids in the presence of the coupling agents 1‐(3‐dimethylaminopropyl)‐3‐ethylcarbodiimide hydrochloride and 4‐dimethylaminopyridine furnished 1,3‐dihexadecanoyl‐2‐docosahexaenoyl glycerol and its unsymmetrical isomer 1,2‐dihexadecanoyl‐3‐docosahexaenoyl glycerol in 99 and 60% yield, respectively. Critical to the success of the unsymmetrical TAG synthesis is the demonstration that PUFA‐containing glycerol acetonides can readily survive appropriately tailored acid‐catalyzed conditions. In this way, sufficient quantities of highly regioisomerically enriched PUFA‐containing unsymmetrical monoacylglycerols (MAG) and TAG have now become routinely accessible. The methods are amenable to scale‐up and could be adopted for regioenriched synthesis of a wide range of TAG.
• FATTY ACID ALCOHOLS
  申请人：Holmeide Anne Kristin

  公开号：US20100266681A1

  公开（公告）日：2010-10-21

  The present invention relates to a lipid composition comprising at least omega-3 polyunsaturated alcohols, or pro-drugs thereof, which omega-3 polyunsaturated alcohols, or pro-drugs thereof, comprising at least (all-Z)-5,8,11,14,17-eicosapentaen-1-ol, or pro-drug thereof, and (all-Z)-4,7,10,13,16,19-docosahexaen-1-ol, or pro-drug thereof, and their use as a pharmaceutical, in particular for the treatment of elevated triglyceride levels. The invention also relates to methods for the preparation of these pro-drugs from marine oils.
• [EN] FATTY ACID ALCOHOLS<br/>[FR] ALCOOLS D'ACIDES GRAS
  申请人：PRONOVA BIOPHARMA NORGE AS

  公开号：WO2008139261A2

  公开（公告）日：2008-11-20

  (EN) The present invention relates to a lipid composition comprising at least omega-3 polyunsaturated alcohols, or pro-drugs thereof, which omega-3 polyunsaturated alcohols, or pro-drugs thereof, comprising at least (all-Z)-5,8,11,14,17-eicosapentaen- 1-ol, or pro-drug thereof, and (all-Z)-4,7,10,13,16,19-docosahexaen-1-ol, or pro-drug thereof, and their use as a pharmaceutical, in particular for the treatment of elevated triglyceride levels. The invention also relates to methods for the preparation of these pro-drugs from marine oils.(FR) La présente invention porte sur une composition lipidique comprenant au moins des alcools polyinsaturés oméga-3, ou des pro-médicaments de ceux-ci, lesquels alcools polyinsaturés oméga-3 ou pro-médicaments de ceux-ci comprennent au moins le (tout-Z)-5,8,11,14,17-eicosapentaène-1-ol, ou un pro-médicament de celui-ci, et le (tout-Z)-4,7,10,13,16,19-docosahexaène-1-ol, ou un pro-médicament de celui-ci, et sur leur utilisation comme produits pharmaceutiques, en particulier pour le traitement de taux élevés de triglycérides. L'invention porte également sur des procédés pour la préparation de ces pro-médicaments à partir d'huiles marines.
• Toxic effects of Gymnodinium cf. mikimotoi unsaturated fatty acids to gametes and embryos of the sea urchin Paracentrotus lividus
  作者：F Sellem

  DOI：10.1016/s0043-1354(99)00181-5

  日期：2000.2

  The toxicity of the main Gymnodinium cf. mikimotoi polyunsaturated fatty acid, has been investigated using the sea urchin gamete and embryo bioassays. The 18:5n3 Fatty acid delays or inhibits first cleavage of Paracentrotus lividus eggs and provokes abnormalities in the embryonic development. These effects were compared with those of other polyunsaturated fatty acids, 18:4n3, 20:5n3 and 22:6n3, which are also present in this al a. A classification of the different fatty acids, based on their effects on sea urchin egg cleavage and thee determination of the half inhibiting concentrations (IC(50)) is proposed. (C) 1999 Elsevier Science Ltd. All rights reserved.