2-arachidonoyl-1,3-dibutyrylglycerol | 1274596-36-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 甘油脂
• 英文名称: 2-arachidonoyl-1,3-dibutyrylglycerol
• 英文别名: 2-((5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoyloxy)propane-1,3-diyl dibutyrate；1,3-di(butanoyloxy)propan-2-yl (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoate
• CAS: 1274596-36-9
• 化学式: C₃₁H₅₀O₆
• 分子量: 518.734
• InChiKey: HSMWLAUBOREKAY-AILJCPQKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.1
• 重原子数：
  37
• 可旋转键数：
  26
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  78.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-arachidonoyl-1,3-dibutyrylglycerol 在 Rhizomucor miehei lipase 、 乙醇 作用下， 反应 24.0h， 以75%的产率得到2-花生酰基甘油
  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
• 作为产物：
  描述：

  正丁酸乙烯酯 在 4-二甲氨基吡啶 、 Candida antarctica lipase 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 9.0h， 生成 2-arachidonoyl-1,3-dibutyrylglycerol
  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

• Chemoenzymatic synthesis of 2-arachidonoylglycerol, an endogenous ligand for cannabinoid receptors
  作者：Subramanian K. Vadivel、Kyle M. Whitten、A. Makriyannis

  DOI：10.1016/j.tetlet.2011.01.047

  日期：2011.3

  A simple and efficient synthesis of 2-arachidonoyl glycerol, an endogenous agonist for cannabinoid receptors was achieved using Novozym 435, immobilized lipase from Candida antarctica.

  使用来自南极念珠菌的固定化脂肪酶 Novozym 435 实现了 2-花生四烯酰甘油（一种大麻素受体的内源性激动剂）的简单有效合成。
• A Methodology for Radiolabeling of the Endocannabinoid 2-Arachidonoylglycerol (2-AG)
  作者：Richard I. Duclos、Meghan Johnston、Subramanian K. Vadivel、Alexandros Makriyannis、Sherrye T. Glaser、S. John Gatley

  DOI：10.1021/jo102277q

  日期：2011.4.1

  The metabolic intermediate and endocannabinoid signaling lipid 2-arachidonoylglycerol (2-AG) has not been readily labeled, primarily because of its instability toward rearrangement. We now detail a synthetic method that easily gives tritiated 2-AG from [5,6,8,9,11,12,14,15-H-3(N)]arachidonic acid in two steps. We utilized a short chain 1,3-diacylglycerol and proceeded through the "structured lipid" [5 '',6 '',8 '',9 '',11 '',12 '', 14 '',15 ''-H-3(N)]2-arachidonoyl-1,3-dibutyrylglycerol, a triacylglycerol that was conveniently deprotected in ethanol with acrylic beads containing Candida antarctica lipase B to give [5 '',6 '',8 '',9 '',11 '',12 '',14 '',15 ''-H-3(N)]2-arachidonoylglycerol ([H-3]2-AG). The flash chromatographic separation necessary to isolate the labeled 2'-acylglycerol [H-3]2-AG resulted in only 4% of the rearrangement byproducts that have been a particular problem with previous methodologies. This reliable "kit" method to prepare the radiolabeled endocannabinoid as needed gave tritiated 2-arachidonoylglycerol [H-3](2)-AG with a specific activity of 200 Ci/mmol for enzyme assays, metabolic studies, and tissue imaging. It has been run on unlabeled materials on over 10 mg scales and should be generally applicable to other 2-acylglycerols.
• 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.