1-linolenoyl-2,3-O-isopropylideneglycerol | 57156-93-1

• 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: 1-linolenoyl-2,3-O-isopropylideneglycerol
• 英文别名: 1,2-acetonide-3-(9,12,15-octadecatrienoyl)glycerol；(2,2-dimethyl-1,3-dioxolan-4-yl)methyl (9Z,12Z,15Z)-octadeca-9,12,15-trienoate
• CAS: 57156-93-1
• 化学式: C₂₄H₄₀O₄
• 分子量: 392.579
• InChiKey: ROCIAKVHQOBBEG-AGRJPVHOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  28
• 可旋转键数：
  16
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 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：

  1-linolenoyl-2,3-O-isopropylideneglycerol 在 4-二甲氨基吡啶 、 三氟乙酸 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 18.0h， 生成 1-linolenoyl-2,3-bis(4-((tert-butoxycarbonyl)amino)butyryl)propane-1,2,3-triol
  参考文献：
  名称：

  γ-氨基丁酸酯。2.γ-氨基丁酸脂质酯的合成，脑吸收和药理特性。

  摘要：

  合成了两种由U-14C标记和未标记的γ-氨基丁酸（GABA）制成的脂质酯，以测试类似于脂质双层膜正常成分的天然脂质类似物可以穿透血脑屏障并将外源GABA转运至大脑。1-亚油酰基-2,3-双（4-氨基丁酰基）丙烷-1,2,3-三醇和1,2-二亚油酰基-3-（4-氨基丁酰基）丙烷-1,2,3-三醇的吸收相对于肝脏，小鼠大脑的自由度分别比游离GABA高75倍和127倍。结果表明，剂量高达0.36 mmol / kg时，GABA酯分子几乎没有血脑屏障。既有酯化合物，也没有游离GABA或脂质成分，都是系统性递送的 通过抑制小鼠的一般运动活动，证明具有中枢神经系统抑制作用。脑组织具有酯酶活性，可以从这些化合物释放GABA。这表明这些化合物作为“前药”在中枢神经系统中释放GABA。

  DOI：

  10.1021/jm00379a019
• 作为产物：
  描述：

  Γ-十八碳三烯酸 、 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 1-linolenoyl-2,3-O-isopropylideneglycerol
  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.
• 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.
• Gaba esters and gaba analogue esters
  申请人：THE McLEAN HOSPITAL CORPORATION

  公开号：EP0133795B1

  公开（公告）日：1989-01-18
• .gamma.-Aminobutyric acid esters. 2. Synthesis, brain uptake, and pharmacological properties of lipid esters of .gamma.-aminobutyric acid
  作者：James N. Jacob、Victor E. Shashoua、Alexander Campbell、Ross J. Baldessarini

  DOI：10.1021/jm00379a019

  日期：1985.1

  than that of free GABA. The results indicate that there is little or no blood-brain barrier for the GABA ester molecules at doses up to 0.36 mmol/kg. Both ester compounds, but neither free GABA nor the lipid components delivered systemically, demonstrated central nervous system depressant properties by inhibiting the general motor activity of mice. Brain tissue has esterase activity which can release

  合成了两种由U-14C标记和未标记的γ-氨基丁酸（GABA）制成的脂质酯，以测试类似于脂质双层膜正常成分的天然脂质类似物可以穿透血脑屏障并将外源GABA转运至大脑。1-亚油酰基-2,3-双（4-氨基丁酰基）丙烷-1,2,3-三醇和1,2-二亚油酰基-3-（4-氨基丁酰基）丙烷-1,2,3-三醇的吸收相对于肝脏，小鼠大脑的自由度分别比游离GABA高75倍和127倍。结果表明，剂量高达0.36 mmol / kg时，GABA酯分子几乎没有血脑屏障。既有酯化合物，也没有游离GABA或脂质成分，都是系统性递送的 通过抑制小鼠的一般运动活动，证明具有中枢神经系统抑制作用。脑组织具有酯酶活性，可以从这些化合物释放GABA。这表明这些化合物作为“前药”在中枢神经系统中释放GABA。
• 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.