4,7,10,13,16,19-二十二碳六烯酸,2-羟基-1-(羟甲基)乙基酯,(4Z,7Z,10Z,13Z,16Z,19Z)- | 175878-30-5

• 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: 4,7,10,13,16,19-二十二碳六烯酸,2-羟基-1-(羟甲基)乙基酯,(4Z,7Z,10Z,13Z,16Z,19Z)-
• 英文名称: 2-docosa-4,7,10,13,16,19-hexaenoyl glycerol
• 英文别名: (4Z,7Z,10Z,13Z,16Z,19Z)-1,3-dihydroxypropan-2-yl docosa-4,7,10,13,16,19-hexaenoate；sn-2 monoacylglyceride of docosahexaenoic acid；2-docosahexaenoylglycerol；MG(0:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/0:0)；1,3-dihydroxypropan-2-yl (4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoate
• CAS: 175878-30-5
• 化学式: C₂₅H₃₈O₄
• 分子量: 402.574
• InChiKey: NHNGEAQTTQPSCX-KUBAVDMBSA-N

物化性质

• 沸点：
  531.5±50.0 °C(Predicted)
• 密度：
  1.002±0.06 g/cm3(Predicted)
• 物理描述：
  Solid

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  29
• 可旋转键数：
  18
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.48
• 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：

  2-((4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoyloxy)propane-1,3-diyl diacetate 在 Rhizomucor miehei lipase 、 乙醇 作用下， 反应 24.0h， 以76%的产率得到4,7,10,13,16,19-二十二碳六烯酸,2-羟基-1-(羟甲基)乙基酯,(4Z,7Z,10Z,13Z,16Z,19Z)-
  参考文献：
  名称：

  Application of chemoenzymatic hydrolysis in the synthesis of 2-monoacylglycerols

  摘要：

  The selective biocatalyzed synthesis of 2-monoacylglycerols (2-MAGs) through the use of commercially available immobilized Candida antarctica (Novozym435) and Rhizomucor miehei is explored. Reactions at room temperature result in the formation of a 2-MAG and a corresponding ethyl ester of the fatty acid with immobilized C. antarctica within 2 h with yields ranging from 36% to 83%. Similar reaction conditions with immobilized R. miehei yielded exclusively the 2-MAG after 24 h with yields ranging from 37% to 88%. Yields vary on the acyl group at the sn-2 position and choice of enzyme involved. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.04.101

文献信息

• Quantitative Method for the Profiling of the Endocannabinoid Metabolome by LC-Atmospheric Pressure Chemical Ionization-MS
  作者：John Williams、JodiAnne Wood、Lakshmipathi Pandarinathan、David A. Karanian、Ben A. Bahr、Paul Vouros、Alexandros Makriyannis

  DOI：10.1021/ac0624086

  日期：2007.8.1

  The endocannabinoid system's biological significance continues to grow as novel endocannabinoid metabolites are discovered. Accordingly, a myopic view of the system that focuses solely on one or two endocannabinoids, such as anandamide or 2-arachidonoyl glycerol, is insufficient to describe the biological responses to perturbations of the system. Rather, the endocannabinoid metabolome as a whole must be analyzed. The work described here is based on liquid chromatography coupled with atmospheric pressure chemical ionization mass spectrometry. This method has been validated to quantify, in a single chromatographic run, the levels of 15 known or suspected metabolites of the endocannabinoid system in the rat brain and is applicable to other biological matrixes. We have obtained an endocannabinoid profile specifically for the frontal cortex of the rat brain and have determined anandamide level differences following the administration of the fatty acid amide hydrolase inhibitor AM374.

  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。
• Structure–Activity Relationships of Fish Oil Derivatives with Antiallergic Activity in Vitro and in Vivo
  作者：In-Hae Kim、Yoshiki Kanayama、Hisashi Nishiwaki、Takuya Sugahara、Kosuke Nishi

  DOI：10.1021/acs.jmedchem.9b00994

  日期：2019.11.14

  antiallergic activity in vitro. Ethanolamides of omega-3 fatty acids (α-linolenic acid, EPA, and DHA) were found to possess promising antiallergic activity, whereas free fatty acids and ethanolamides of other fatty acids exhibited no or weak potency. Based on this finding, structure–activity relationships of DHA-ethanolamide (DHEA) derivatives were investigated to yield better fatty acid derivatives with enhanced

  探索了鱼油中的一系列不饱和脂肪酸及其相应的乙醇酰胺代谢物，以发现具有抗过敏活性的活性鱼油成分。发现ω-3脂肪酸的乙醇酰胺（α-亚麻酸，EPA和DHA）具有良好的抗过敏活性，而游离脂肪酸和其他脂肪酸的乙醇酰胺则没有或表现出弱的功效。基于这一发现，研究了DHA-乙醇酰胺（DHEA）衍生物的结构-活性关系，以在体内和体外产生具有增强的抗过敏活性的更好的脂肪酸衍生物。当DHEA的乙醇酰胺部分被取代的磺酰胺官能团取代时，在体外提供了非常有前途的效价。化合物59在体内显示出比DHEA更高的抗过敏活性。结果表明，优化的DHEA衍生物在体内和体外具有增强的抗过敏活性，并且所得结构将成为进一步开发具有良好抗过敏活性的生物利用性衍生物的重要基础。
• Enzymatic synthesis of triacylglycerols of docosahexaenoic acid: Transesterification of its ethyl esters with glycerol
  作者：S. Moreno-Perez、P. Luna、F.J. Señorans、J.M. Guisan、G. Fernandez-Lorente

  DOI：10.1016/j.foodchem.2015.04.095

  日期：2015.11

  The synthesis of docosahexaenoyl triacylglycerides at low temperature (e.g., 50 °C) using biocatalysts of 6 commercial lipases adsorbed on hydrophobic supports was studied. In general, the triacylglyceride yields were very low with the exceptions of those produced with the enzymes from Candida antarctica fraction B, CALB (82%), and those produced with the enzyme from Pseudomonas fluorescens, PFL (57%)

  研究了在低温（例如50°C）下使用吸附在疏水性载体上的6种商业脂肪酶的生物催化剂合成二十二碳六烯酰基甘油三酯的方法。通常，除了用南极假丝酵母组分B的酶CALB（82％）和用荧光假单胞菌PFL的酶（57％）生产的那些外，甘油三酸酯的收率都非常低。反应在真空下进行以除去释放的乙醇。当使用不同的CALB衍生物时，收率差异很大，而当CALB吸附在疏水性载体上时，收率更高（82％）。一种有趣的副产品（占锡的18％在合成过程的最后保留了-2 DHA单酰基甘油酯。与商业衍生物Novozym 435相比，吸附在Sepabeads上的CALB具有更好的活性和稳定性。在反应条件下30天后，最好的CALB生物催化剂保留了90％的活性。
• Application of chemoenzymatic hydrolysis in the synthesis of 2-monoacylglycerols
  作者：Kyle M. Whitten、Alexandros Makriyannis、Subramanian K. Vadivel

  DOI：10.1016/j.tet.2012.04.101

  日期：2012.7

  The selective biocatalyzed synthesis of 2-monoacylglycerols (2-MAGs) through the use of commercially available immobilized Candida antarctica (Novozym435) and Rhizomucor miehei is explored. Reactions at room temperature result in the formation of a 2-MAG and a corresponding ethyl ester of the fatty acid with immobilized C. antarctica within 2 h with yields ranging from 36% to 83%. Similar reaction conditions with immobilized R. miehei yielded exclusively the 2-MAG after 24 h with yields ranging from 37% to 88%. Yields vary on the acyl group at the sn-2 position and choice of enzyme involved. (c) 2012 Elsevier Ltd. All rights reserved.