(2,2-二甲基-1,3-二氧戊环-4-基)甲基肉豆蔻酸酯 | 56630-71-8

• 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: (2,2-二甲基-1,3-二氧戊环-4-基)甲基肉豆蔻酸酯
• 英文名称: (2,2-dimethyl-1,3-dioxolane-4-yl)methyl myristate
• 英文别名: isopropylidene glycerol myristate；Tetradecanoic acid, (2,2-dimethyl-1,3-dioxolan-4-yl)methyl ester；(2,2-dimethyl-1,3-dioxolan-4-yl)methyl tetradecanoate
• CAS: 56630-71-8
• 化学式: C₂₀H₃₈O₄
• 分子量: 342.519
• InChiKey: PYLQQVMOUCHKEQ-UHFFFAOYSA-N

物化性质

• 熔点：
  44.7 °C
• 沸点：
  410.2±25.0 °C(Predicted)
• 密度：
  0.938±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  24
• 可旋转键数：
  15
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.95
• 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：

  (2,2-二甲基-1,3-二氧戊环-4-基)甲基肉豆蔻酸酯 在 吡啶 、 4-二甲氨基吡啶 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 6.08h， 生成 Glycerol, 1-myristate-3-palmitate, 2-OTMS-
  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：

  肉豆蔻酸 在 硫酸 、 potassium carbonate 作用下， 反应 34.5h， 生成 (2,2-二甲基-1,3-二氧戊环-4-基)甲基肉豆蔻酸酯
  参考文献：
  名称：

  Monomyristin 和 Monopalmitin 衍生物：作为潜在的抗菌和抗真菌剂的合成和评价

  摘要：

  在目前的工作中，以市售的肉豆蔻酸和棕榈酸为原料，成功地制备了单酰基甘油衍生物，即 1-单肉豆蔻素、2-单肉豆蔻素和 2-单棕榈酸。1-单肉豆蔻碱化合物是通过肉豆蔻酸乙酯和1,2-O-异亚丙基甘油之间的酯交换反应制备的，该反应是用丙酮保护甘油得到的，然后使用Amberlyst-15脱保护。另一方面，2-单酰基甘油衍生物是在疏毛嗜热丝孢菌脂肪酶存在下通过甘油三酯的酶水解制备的。使用傅里叶变换红外 (FTIR) 分光光度计、气相或液相色谱-质谱仪 (GC-MS 或 LC-MS) 分析合成产物，以及质子和碳核磁共振（1H-和 13C-NMR）光谱仪。发现单肉豆蔻酸具有很高的抗菌和抗真菌活性，而 2-单棕榈酸则完全没有任何活性。与阳性对照相比，1-单肉豆蔻素化合物对金黄色葡萄球菌和聚集放线菌显示出更高的抗菌活性，并且对白色念珠菌具有更高的抗真菌活性。同时，2-monoryristin 对大肠杆菌表现

  DOI：

  10.3390/molecules23123141

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.
• 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.
• Preparation of Diacid 1,3-Diacylglycerols
  作者：R. John Craven、Robert W. Lencki

  DOI：10.1007/s11746-010-1625-7

  日期：2010.11

  syntheses; recrystallization and flash chromatography for purification of partial acylglycerols; and thin‐layer chromatography (TLC) separation of DAG. For this work, 1‐MAG intermediates and subsequent diacid 1,3‐DAG were prepared using non‐enzymatic methods, whereas, monoacid 1,3‐DAG were prepared by enzymatic methods. It was not always possible to obtain pure samples of target compounds—in recrystallizations

  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。
• Monomyristin and Monopalmitin Derivatives: Synthesis and Evaluation as Potential Antibacterial and Antifungal Agents
  作者：Jumina、Asma Nurmala、Anggit Fitria、Deni Pranowo、Eti Sholikhah、Yehezkiel Kurniawan、Bambang Kuswandi

  DOI：10.3390/molecules23123141

  日期：——

  showed high antibacterial and antifungal activities, while 2-monopalmitin did not show any activity at all. The 1-monomyristin compound showed higher antibacterial activity against Staphylococcus aureus and Aggregatibacter actinomycetemcomitans and also higher antifungal activity against Candida albicans compared to the positive control. Meanwhile, 2-monomyristin showed high antibacterial activity against

  在目前的工作中，以市售的肉豆蔻酸和棕榈酸为原料，成功地制备了单酰基甘油衍生物，即 1-单肉豆蔻素、2-单肉豆蔻素和 2-单棕榈酸。1-单肉豆蔻碱化合物是通过肉豆蔻酸乙酯和1,2-O-异亚丙基甘油之间的酯交换反应制备的，该反应是用丙酮保护甘油得到的，然后使用Amberlyst-15脱保护。另一方面，2-单酰基甘油衍生物是在疏毛嗜热丝孢菌脂肪酶存在下通过甘油三酯的酶水解制备的。使用傅里叶变换红外 (FTIR) 分光光度计、气相或液相色谱-质谱仪 (GC-MS 或 LC-MS) 分析合成产物，以及质子和碳核磁共振（1H-和 13C-NMR）光谱仪。发现单肉豆蔻酸具有很高的抗菌和抗真菌活性，而 2-单棕榈酸则完全没有任何活性。与阳性对照相比，1-单肉豆蔻素化合物对金黄色葡萄球菌和聚集放线菌显示出更高的抗菌活性，并且对白色念珠菌具有更高的抗真菌活性。同时，2-monoryristin 对大肠杆菌表现