(2,2-dimethyl-1,3-dioxolan-4-yl)methyl (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoate | 953393-65-2

• 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: (2,2-dimethyl-1,3-dioxolan-4-yl)methyl (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoate
• CAS: 953393-65-2
• 化学式: C₂₆H₄₂O₄
• 分子量: 418.617
• InChiKey: ZWEJNTPCOYFONY-GKFVBPDJSA-N

物化性质

• 沸点：
  503.7±50.0 °C(Predicted)
• 密度：
  0.954±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  30
• 可旋转键数：
  17
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2,2-dimethyl-1,3-dioxolan-4-yl)methyl (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoate 在 硼酸 作用下， 以 甲乙醚 为溶剂， 生成 2-arachidonyl-glycerol
  参考文献：
  名称：

  Monoglycerides from the brown alga Sargassum sagamianum: Isolation, synthesis, and biological activity

  摘要：

  Polyunsaturated fatty acid-derived monoglycerides were characterized from the marine brown alga Sargassum sagamianum, collected from Jeju Island, Korea. A new compound of this structural class was isolated and determined to be 1-octadecatetraenoyl glycerol, by combined spectroscopic methods. Based on the structures and bioactivity of these compounds, a series of monoglycerides were synthesized using glycerol and various fatty acids. Several compounds exhibited moderate to significant inhibition of phospholipase A(2) and cyclooxygenase-2. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.05.008
• 作为产物：
  描述：

  花生四烯酸 、 丙酮缩甘油 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 生成 (2,2-dimethyl-1,3-dioxolan-4-yl)methyl (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoate
  参考文献：
  名称：

  Monoglycerides from the brown alga Sargassum sagamianum: Isolation, synthesis, and biological activity

  摘要：

  Polyunsaturated fatty acid-derived monoglycerides were characterized from the marine brown alga Sargassum sagamianum, collected from Jeju Island, Korea. A new compound of this structural class was isolated and determined to be 1-octadecatetraenoyl glycerol, by combined spectroscopic methods. Based on the structures and bioactivity of these compounds, a series of monoglycerides were synthesized using glycerol and various fatty acids. Several compounds exhibited moderate to significant inhibition of phospholipase A(2) and cyclooxygenase-2. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.05.008

文献信息

• Biochemical characterization of the PHARC-associated serine hydrolase ABHD12 reveals its preference for very-long-chain lipids
  作者：Alaumy Joshi、Minhaj Shaikh、Shubham Singh、Abinaya Rajendran、Amol Mhetre、Siddhesh S. Kamat

  DOI：10.1074/jbc.ra118.005640

  日期：2018.11

  Polyneuropathy, hearing loss, ataxia, retinitis pigmentosa, and cataract (PHARC) is a rare genetic human neurological disorder caused by null mutations to the Abhd12 gene, which encodes the integral membrane serine hydrolase enzyme ABHD12. Although the role that ABHD12 plays in PHARC is understood, the thorough biochemical characterization of ABHD12 is lacking. Here, we report the facile synthesis of mono-1-(fatty)acyl-glycerol lipids of varying chain lengths and unsaturation and use this lipid substrate library to biochemically characterize recombinant mammalian ABHD12. The substrate profiling study for ABHD12 suggested that this enzyme requires glycosylation for optimal activity and that it has a strong preference for very-long-chain lipid substrates. We further validated this substrate profile against brain membrane lysates generated from WT and ABHD12 knockout mice. Finally, using cellular organelle fractionation and immunofluorescence assays, we show that mammalian ABHD12 is enriched on the endoplasmic reticulum membrane, where most of the very-long-chain fatty acids are biosynthesized in cells. Taken together, our findings provide a biochemical explanation for why very-long-chain lipids (such as lysophosphatidylserine lipids) accumulate in the brains of ABHD12 knockout mice, which is a murine model of PHARC.
• Structure−Activity Relationship of a Series of Inhibitors of Monoacylglycerol HydrolysisComparison with Effects upon Fatty Acid Amide Hydrolase
  作者：José Antonio Cisneros、Séverine Vandevoorde、Silvia Ortega-Gutiérrez、Clément Paris、Christopher J. Fowler、María L. López-Rodríguez

  DOI：10.1021/jm070642y

  日期：2007.10.1

  A series of 32 heterocyclic analogues based on the structure of 2-arachidonoylglycerol (2-AG) were synthesized and tested for their ability to inhibit monoacylglycerol lipase and fatty acid an-tide hydrolase activities. The designed compounds feature a hydrophobic moiety and different heterocyclic subunits that mimic the glycerol fragment. This series has allowed us to carry out the first systematic structure activity relationship study on inhibition of 2-AG hydrolysis. The most promising compounds were oxiran-2-ylmethyl (5Z,8Z,l 11Z,14Z)-icosa-5,8,11,14-tetraenoate (1) and tetrahydro-2H-pyran-2-ylmethyl (5Z,8Z,11Z,14z)-icosa5,8,11,14-tetraenoate (5). They inhibited cytosolic 2-oleoylglycerol (2-OG) hydrolysis completely (IC50 values of 4.5 and 5.6 mu M, respectively). They also blocked, albeit less potently, 2-OG hydrolysis in membrane fractions (IC50 values of 19 and 26,mu M, respectively) and anandamide hydrolysis (IC50 values of 12 and 51 mu M, respectively). These compounds will be useful in delineating the importance of the cytosolic hydrolytic activity in the regulation of 2-AG levels and, hence, its potential as a target for drug development.
• Monoglycerides from the brown alga Sargassum sagamianum: Isolation, synthesis, and biological activity
  作者：Hyeun Wook Chang、Kyoung Hwa Jang、Doohyun Lee、Hee Ryong Kang、Tae-Yoon Kim、Bong Ho Lee、Byoung Wook Choi、Sanghee Kim、Jongheon Shin

  DOI：10.1016/j.bmcl.2008.05.008

  日期：2008.6

  Polyunsaturated fatty acid-derived monoglycerides were characterized from the marine brown alga Sargassum sagamianum, collected from Jeju Island, Korea. A new compound of this structural class was isolated and determined to be 1-octadecatetraenoyl glycerol, by combined spectroscopic methods. Based on the structures and bioactivity of these compounds, a series of monoglycerides were synthesized using glycerol and various fatty acids. Several compounds exhibited moderate to significant inhibition of phospholipase A(2) and cyclooxygenase-2. (C) 2008 Elsevier Ltd. All rights reserved.