1-亚麻酰-2,3-异亚丙基-外消旋-甘油 | 127592-95-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 1-亚麻酰-2,3-异亚丙基-外消旋-甘油
• 中文别名: 1-油烯基-2,3-异亚丙基-rac-甘油
• 英文名称: 1,2-acetonide-3-(9,12-octadecadienoyl)glycerol
• 英文别名: (2,2-dimethyl-1,3-dioxolan-4-yl)methyl linoleate；(+/-)-2,2-dimethyl-1,3-dioxolan-4-ylmethyl (9Z,12Z)-9,12-octadecadienoate；1-Linoleoyl-2,3-isopropylidene-rac-glycerol；(2,2-dimethyl-1,3-dioxolan-4-yl)methyl (9Z,12Z)-octadeca-9,12-dienoate
• CAS: 127592-95-4
• 化学式: C₂₄H₄₂O₄
• 分子量: 394.595
• InChiKey: OGLQRMONVRWDKV-MURFETPASA-N

物化性质

• 沸点：
  472.3±40.0 °C(Predicted)
• 密度：
  0.943±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于氯仿（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  28
• 可旋转键数：
  17
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.79
• 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-亚麻酰-2,3-异亚丙基-外消旋-甘油 在 吡啶 、 4-二甲氨基吡啶 、 水 、 溶剂黄146 作用下， 以 苯 为溶剂， 反应 2.25h， 生成 (+/-)-2,3-di[(E)-2-methyl-2-butenoyloxy]propyl (9Z,12Z)-9,12-octadecadienoate
  参考文献：
  名称：

  信息素合成。第253部分：果蝇雄性果蝇甘油三酸酯的外消旋物和对映体的合成，特别着重于对映体纯的1-甘油单酸酯的制备

  摘要：

  蝇果蝇的果蝇的外消旋体和对映异构体（2，3-丙酮甘油的外消旋体和对映异构体）通过三个步骤合成了甘油三酸酯1a – e（果蝇的果蝇的棕榈酸，棕榈油酸，硬脂酸，油酸和亚油酸的2,3-二聚二羟甲氧基丙基酯）。（2）通过1-甘油单酸酯4a - e衍生自上述脂肪酸。建立了制备对映体纯的1-甘油单酸酯4a - e的适当条件，并通过相应的bis-（R）-MTPA酯的NMR分析确定了它们的对映体纯度。

  DOI：

  10.1016/j.tet.2012.07.086
• 作为产物：
  描述：

  (Z,Z)-9,12-十八烷二烯酸二聚物 、 丙酮缩甘油 在 tetrabutylammonium tetramethylborate 作用下， 以 甲苯 为溶剂， 反应 3.0h， 以97.08%的产率得到1-亚麻酰-2,3-异亚丙基-外消旋-甘油
  参考文献：
  名称：

  含氧生物燃料：用磺化二氧化硅和（Bu 4 N）（BF 4）催化剂的混合物合成脂肪酸Solketal酯

  摘要：

  用甘油和丙酮一步法制备表面积较小，1.32 mmol H + / g的无定形SiO 2 -SO 3 H [1] 。发现20％-w / w的催化剂混合物（10％[1]和10％（Bu 4 N）（BF 4））对于合成二油基醚和含氧生物燃料，脂肪酸，油基酯（FASEs）非常有效。通过将辛酸，月桂酸，硬脂酸，油酸和亚油酸与邻苯二酚在回流的甲苯中以4：1的酸：己二醛比例直接酯化，还可以定量获得乙酸丁二酯。

  DOI：

  10.1016/j.catcom.2018.12.005

文献信息

• Evaluation of a glycerol derived biofuel by thermal analysis
  作者：Luciano N. Batista、Rosane A. S. San Gil、Luciana B. R. Lopes、Vera L. P. Soares

  DOI：10.1007/s10973-011-1558-x

  日期：2011.12

  This work describes thermal analysis evaluation of a glycerol derived compound (fatty acid esters of (2,2-dimethyl-1,3-dioxolan-4-yl) methanol) developed to work as a biofuel. Mixtures of these ketal–glyceryl esters with fatty acid methyl esters typical of soybean biodiesel were prepared and evaluated in relation to biodiesel critical thermal properties such as temperature of crystallization, thermal stability and volatilization measured by differential scanning calorimetry and thermogravimetric analysis. The volatility of the products containing fatty acid methyl esters and (2,2-dimethyl-1,3-dioxolan-4-yl) methyl esters could be predicted by thermogravimetric analyses conducted in nitrogen that avoided time consuming distillation and greatly reduced material expenditure.

  这项工作描述了对一种甘油衍生化合物（（2,2-二甲基-1,3-二氧戊环-4-基）甲醇脂肪酸酯）的热分析评估，该化合物被开发用作生物燃料。制备了这些缩酮甘油酯与典型的大豆生物柴油脂肪酸甲酯的混合物，并通过差示扫描量热仪和热重分析法对生物柴油的关键热特性（如结晶温度、热稳定性和挥发性）进行了评估。通过在氮气中进行热重分析，可以预测含有脂肪酸甲酯和（2,2-二甲基-1,3-二氧戊环-4-基）甲酯的产品的挥发性，从而避免了耗时的蒸馏，并大大减少了材料支出。
• 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.
• 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.
• Study of the Effect of DATEM. 1. Influence of Fatty Acid Chain Length on Rheology and Baking
  作者：Peter Köhler、Werner Grosch

  DOI：10.1021/jf980891i

  日期：1999.5.1

  To answer the question of which fatty acid residue is the most effective, diacetyltartaric esters of monoglycerides (DATEMs) with fatty acids of chain lengths 6:0-20:0 were synthesized. The activity of synthesized DATEMs and commercial DATEM products was studied by means of rheological methods and a microscale baking test with 10 g of flour. Variation of the acyl residue from 6:0 to 22:0 showed that stearic acid (18:0) had the best effect on the baking activity of DATEM (loaf volume increased by 62%). DATEMs containing unsaturated fatty acids (18:1, 18:2) or DATEMs produced from diacylglycerols instead of monoacylglycerols showed a slight increase of the loaf volumes. A slight effect of DATEM on the rheology of dough was observed. However, much greater was the effect on the gluten isolated from doughs prepared with DATEM. The resistance of gluten to extension was increased after the addition of increasing amounts of DATEM (0.1-0.5%). Within the series of DATEMs derived from the homologous series of monoacylglycerols the product based on glycerol monostearate (18:0) showed a maximum increase of the gluten resistance.
• ——
  作者：Junko Onodera、Shigeru Matsuyama、Takahisa Suzuki、Koichi Fujii

  DOI：10.1023/a:1016285801824

  日期：——

  Host-recognizing kairomones for the stinging behavior of the parasitic wasp, Anisopteromalus calandrae, were identified on host azuki bean weevil larvae, Callosobruchus chinensis (L.). The kairomones were extracted with acetone from Chinese green beans, from which emerged wasps and host weevils had been removed. The kairomones are a mixture of triacylglycerols and fatty acids, each of which is separately active, and with no observable synergistic effect between them. These compounds are known to be constituents of an oviposition-marking pheromone of host azuki bean weevils. However, they differ from the previously reported saturated hydrocarbons and diacylglycerols of the kairomone that another parasitic wasp, Dinarmus basalis, uses for the host recognition of C. chinensis. Thus, A. calandrae and D. basalis selectively utilize different constituents of the oviposition-marking pheromone of C. chinensis as host-recognizing kairomones.