(2,2-dimethyl-1,3-dioxolan-4-yl)methyl dodecanoate | 40630-75-9

• 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 dodecanoate
• 英文别名: (2,2-dimethyl-1,3-dioxolane-4-yl)methyl laurate；rac-1,2-isopropylidene-3-dodecanoylglycerol；(+/-)-4-lauroyloxymethyl-2,2-dimethyl-[1,3]dioxolane；(+/-)-4-Lauroyloxymethyl-2,2-dimethyl-[1,3]dioxolan；4-Lauroyloxymethyl-2,2-dimethyl-[1,3]dioxolan；2,3-(Dimethylmethyldioxy)propyl-laurinat；Dodecanoic acid, (2,2-dimethyl-1,3-dioxolan-4-yl)methyl ester
• CAS: 40630-75-9
• 化学式: C₁₈H₃₄O₄
• 分子量: 314.466
• InChiKey: MCDFASABJWCJAA-UHFFFAOYSA-N

物化性质

• 熔点：
  32.5 °C
• 沸点：
  381.1±22.0 °C(Predicted)
• 密度：
  0.947±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  22
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 海关编码：
  2932999099

反应信息

• 作为反应物：
  描述：

  (2,2-dimethyl-1,3-dioxolan-4-yl)methyl dodecanoate 在 吡啶 作用下， 以 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 6.0h， 生成 1-hexanoyl-3-lauroyl-rac-glycerol
  参考文献：
  名称：

  二酸1,3-二酰基甘油的制备

  摘要：

  介绍了制备1,3-DAG的完整方法（包括合成，纯化和分析）。对于成功的综合项目，应考虑每个特定过程的优点和缺点，并应采取措施来弥补或平衡潜在的缺点。为此，我们描述了与以下相关的一些挑战：化学和酶催化的酰基甘油合成；重结晶和快速色谱法纯化部分酰基甘油；和DAG的薄层色谱（TLC）分离。对于这项工作，使用非酶法制备1-MAG中间体和随后的二酸1,3-DAG，而通过酶法制备单酸1,3-DAG。f。此外，DAG的TLC R f由两个主要因素决定：酰基链长度和位置异构性。有趣的是，虽然位置异构的作用众所周知，但酰基链长度在这些分离中的作用只是最近才被发现。

  DOI：

  10.1007/s11746-010-1625-7
• 作为产物：
  描述：

  月桂酸 、 丙酮缩甘油 以 二氯甲烷 为溶剂， 反应 24.0h， 以86%的产率得到(2,2-dimethyl-1,3-dioxolan-4-yl)methyl dodecanoate
  参考文献：
  名称：

  氯化三酰基甘油的合成及串联质谱

  摘要：

  使用酶催化的酰化和保护基策略掺入9,10-二氯十八烷酰基基团产生了二氯化和四氯化三酰基甘油的特定区域异构体。六氯和六溴三酰基甘油是通过将氯或溴加到三（-顺式）中而合成的-9-十八碳烯基甘油）。在电喷雾电离和串联质谱分析中，所有含有9,10-二氯十八烷酰基的化合物的钠加成离子在发生碰撞诱导的离解时，很容易失去两个HCl分子。提出了描述HCl连续损失和共轭二烯形成的机理，以防止烷基链上的两个邻氯原子损失。这种特征性的碎片行为和特征性标准品的可用性将促进定量分析方法的发展，用于测定从海洋和其他生物来源中分离出的脂质混合物中的氯化三酰甘油。

  DOI：

  10.1016/j.chemphyslip.2013.07.001

文献信息

• Oxygenated biofuels: Synthesis of fatty acid solketal esters with a mixture of sulfonated silica and (Bu4N)(BF4) catalyst
  作者：Sandro L. Barbosa、Pamela C. Lima、Wallans T.P. dos Santos、Stanlei I. Klein、Giuliano C. Clososki、Franco J. Caires

  DOI：10.1016/j.catcom.2018.12.005

  日期：2019.2

  Amorphous SiO2-SO3H [1] with a small surface area and 1.32-mmol H+/g was used for the one-step preparation of solketal from glycerol and acetone; a 20%-w/w catalyst mixture (10% [1] and 10% (Bu4N)(BF4) was found to be very efficient for the synthesis of disolketal ether and of oxygenated biofuels fatty acids solketal esters (FASEs), by direct esterification of the caprylic, lauric, stearic, oleic and

  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。
• Synthesis of the Fatty Esters of Solketal and Glycerol-Formal: Biobased Specialty Chemicals
  作者：Alvise Perosa、Andrea Moraschini、Maurizio Selva、Marco Noè

  DOI：10.3390/molecules21020170

  日期：——

  The caprylic, lauric, palmitic and stearic esters of solketal and glycerol formal were synthesized with high selectivity and in good yields by a solvent-free acid catalyzed procedure. No acetal hydrolysis was observed, notwithstanding the acidic reaction conditions.

  通过无溶剂酸催化方法以高选择性和高产率合成了醇缩酮和甘油缩甲醛的辛酸酯、月桂酸酯、棕榈酸酯和硬脂酸酯。尽管存在酸性反应条件，但未观察到缩醛水解。
• 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.
• 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.
• Lipase-mediated desymmetrization of glycerol with aromatic and aliphatic anhydrides
  作者：Daniela I. Batovska、Shuichirou Tsubota、Yasuo Kato、Yasuhisa Asano、Makoto Ubukata

  DOI：10.1016/j.tetasy.2004.09.033

  日期：2004.11

  Chirazyme L-2 (Candida antarctica) catalyzed esterification of glycerol with aromatic and aliphatic anhydrides in 1,4-dioxane is described. All the aromatic monoacylglycerols (MAGs) were produced as (R)-enantiomers, while aliphatic MAGs were obtained either as racemic mixtures or the (S)-enantiomers. The influence of substituted aromatic rings, chain length, and presence of a conjugated double bond in the acyl donor moiety on the enantiotopic selectivity as well as the efficiency of the enzyme was studied. (C) 2004 Elsevier Ltd. All rights reserved.