2-eicosa-5,8,11,14,17-pentaenoyl glycerol

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 内源性大麻素
• 英文名称: 2-eicosa-5,8,11,14,17-pentaenoyl glycerol
• 英文别名: 2-eicosapentaenoylglycerol；2-Eicosapentaenoyl-glycerol；1,3-dihydroxypropan-2-yl (5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoate
• 化学式: C₂₃H₃₆O₄
• 分子量: 376.536
• InChiKey: IXSYVBCFIGEECR-JLNKQSITSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  27
• 可旋转键数：
  17
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  全顺式二十碳五烯酸 、 甘油 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 乙腈 为溶剂， 生成 2-eicosa-5,8,11,14,17-pentaenoyl glycerol
  参考文献：
  名称：

  Quantitative Method for the Profiling of the Endocannabinoid Metabolome by LC-Atmospheric Pressure Chemical Ionization-MS

  摘要：

  内源性大麻素系统的生物学重要性随着新型内源性大麻素代谢物的发现而不断增长。因此，单纯关注一种或两种内源性大麻素（如大麻二酚或2-花生四烯酸甘油酯）的狭隘观点不足以描述系统扰动引起的生物反应。相反，必须分析内源性大麻素代谢组作为一个整体。此处描述的工作基于与大气压力化学电离质谱联用的液相色谱法。该方法已被验证可以在一次色谱运行中定量测定大鼠脑内15种已知或嫌疑的内源性大麻素代谢物的水平，并且适用于其他生物基质。我们获得了大鼠脑额叶特定的内源性大麻素谱，并在给予脂肪酸酰胺水解酶抑制剂AM374后，确定了大麻二酚水平的差异。

  DOI：

  10.1021/ac0624086

文献信息

• Sn-1(3) Monoacylglycerides and lipid absorption
  申请人：Nestec S.A.

  公开号：EP2508180A1

  公开（公告）日：2012-10-10

  The present invention relates generally to the field of lipids and in particular aims at improving lipid absorption, for example under conditions of lipid maldigestion or malabsorption. One embodiment of the present invention relates to a composition comprising sn-1(3) monoacylglycerols, wherein the sn-1 or sn-3 position is occupied by an acyl group such as a fatty acid and the sn-2 position remains unoccupied. The fatty acid may be one with anti-inflammatory properties.

  本发明一般涉及脂质领域，尤其旨在改善脂质的吸收，例如在脂质消化不良或吸收不良的情况下。本发明的一个实施方案涉及一种包含 sn-1(3)单酰基甘油的组合物，其中 sn-1 或 sn-3 位置被脂肪酸等酰基占据，而 sn-2 位置未被占据。脂肪酸可以是具有抗炎特性的脂肪酸。
• SN-1(3) MONOACYLGLYCERIDES AND LIPID ABSORPTION
  申请人：Nestec S.A.

  公开号：EP3135283A1

  公开（公告）日：2017-03-01

  The present invention relates generally to the field of lipids and in particular aims at improving lipid absorption, for example under conditions of lipid maldigestion or malabsorption. One embodiment of the present invention relates to a composition comprising sn-1(3) monoacylglycerols, wherein the sn-1 or sn-3 position is occupied by an acyl group such as a fatty acid and the sn-2 position remains unoccupied. The fatty acid may be one with anti-inflammatory properties.

  本发明一般涉及脂质领域，尤其旨在改善脂质的吸收，例如在脂质消化不良或吸收不良的情况下。本发明的一个实施方案涉及一种包含 sn-1(3)单酰基甘油的组合物，其中 sn-1 或 sn-3 位置被脂肪酸等酰基占据，而 sn-2 位置未被占据。脂肪酸可以是具有抗炎特性的脂肪酸。
• Comparison of acyl donors for lipase-catalyzed production of 1,3-dicapryloyl-2-eicosapentaenoylglycerol
  作者：Roxana Irimescu、Kazuhiko Hata、Yugo Iwasaki、Tsuneo Yamane

  DOI：10.1007/s11746-001-0221-3

  日期：2001.1

  AbstractSynthesis of 1,3‐dicapryloyl‐2‐eicosapentaenoylglycerol (CEC) catalyzed by Lipozyme IM (immobilized Rhizomucor miehei lipase) was performed by interesterification of trieicosapentaenoylglycerol (EEE) with caprylic acid (CA) (acidolysis) and EEE with ethyl caprylate (EtC) (interesterification). Both methods involved two steps: (i) transesterification at an optimized water content and temperature for the high yield conversion of the substrate to CEC, 1‐capryloyl‐2‐eicosapentaenoylglycerol (CEOH) and 2‐eicosapentaenoylglycerol (OHEOH), and (ii) reesterification of CEOH and OHEOH to CEC by water removal under reduced pressure. Interesterification had clear advantages over acidolysis. The reaction rates for interesterification were higher and the reaction times shorter. The final yield of CEC by interesterification was higher, and the extent of acyl migration, indicated by the tricapryloylglycerol content, was lower. The disadvantage of the higher price of EtC used for interesterification (approximately 10 times higher than the price of CA) was overcome by synthesizing it directly in the same reaction vessel prior to the interesterification step. EtC was rapidly synthesized by esterification of CA with ethanol in high yield (92% obtained in 2.5 h). The amount of water added to the reaction mixture and the reaction temperature influenced the yields of CEC, CEOH, and OHEOH in the transesterification step for both interesterification and acidolysis methods. The regioisomeric purity of CEC was 100% for both methods at temperatures of 40°C or less. The highest yield of CEC (81%) was obtained for the interesterification of EEE with EtC, formed directly in the same reaction vessel, at a CA/EEE molar ratio of 20∶1 and 30°C.
• NUTRITIONAL COMPOSITIONS COMPRISING SN-1 (3) MONOACYLGLYCEROLS FOR USE IN THE TREATMENT OF MALABSORPTION OR MALDIGESTION IN INFANTS OR YOUNG CHILDREN
  申请人：NESTEC S.A.

  公开号：US20170332691A1

  公开（公告）日：2017-11-23

  The present invention refers to nutritional composition comprising sn-1(3) monoacylglycerols for use in the treatment or prevention of maldigestion and/or malabsorption in an infant or young child. It also refers to a nutritional composition comprising sn-1(3) monoacylglycerols for use to increase lipid (e.g. fatty acids) absorption/delivery and/or to increase the energy or the mineral bioavailability in an infant or young child. The infant or young child may have a gut immaturity and/or a reduced enteral feeding tolerance. They may also be pretermand/or low birth weight.
• US9000039B2
  申请人：——

  公开号：US9000039B2

  公开（公告）日：2015-04-07