1,2-二己酰甘油 | 17598-91-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 甘油脂
• 中文名称: 1,2-二己酰甘油
• 英文名称: 1,2-dihexanoylglycerol
• 英文别名: O,O-1,2-dihexanoylglycerol；(2-hexanoyloxy-3-hydroxypropyl) hexanoate
• CAS: 17598-91-3
• 化学式: C₁₅H₂₈O₅
• 分子量: 288.384
• InChiKey: DRUFTGMQJWWIOL-UHFFFAOYSA-N

物化性质

• 沸点：
  372.0±9.0 °C(Predicted)
• 密度：
  1.005 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  20
• 可旋转键数：
  14
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1,2-二己酰甘油 在 三乙胺 、 三氯氧磷 作用下， 以 四氢呋喃 为溶剂， 生成
  参考文献：
  名称：

  Effect of synthetic and natural phospholipids on N-acylphosphatidylethanolamine-hydrolyzing phospholipase D activity

  摘要：

  N-Acylethanolamines (NAEs) constitute a family of endogenous bioactive lipids that includes arachidonoylethanolamide (anandamide), palmitoylethanolamide (PEA) and oleoylethanolamide (OEA). These lipids are formed from their respective N-acylated ethanolamine phospholipid (NAPE) precursor by the action of a phospholipase D enzyme (NAPE-PLD). Anandamide, OEA, and PEA are all bioactive lipids that may influence, amongst others: neuroinflammation, food intake, and oocyte implantation. Here we have synthesized a number of NAPE analogues with variation in the phosphoester structure. The NAPE analogues as well as selected phospholipids and beta-lactamase substrates were tested as potential modifiers of cloned human NAPE-PLD in an enzyme assay involving a C-14-labeled diether-NAPE substrate. One hit was identified, namely 1,2-dihexanoyl-glycero-N-(3-(tetradecanoylamino)propyl)phosphoramidate (AHP-71B) which showed inhibitory activity and may serve as template for further structure-activity developments. Furthermore, it was found that NAPE-PLD was activated by phosphatidylethanolamine and inhibited by the beta-lactamase substrate nitrocefin. (C) 2009 Elsevier Ireland Ltd. All rights reserved.

  DOI：

  10.1016/j.chemphyslip.2009.08.005
• 作为产物：
  描述：

  Hexanoic acid 1-benzyloxymethyl-2-hexanoyloxy-ethyl ester 在 钯 氢气 作用下， 以 正庚烷 为溶剂， 生成 1,2-二己酰甘油
  参考文献：
  名称：

  Zhelvakova,E.G. et al., Journal of Organic Chemistry USSR (English Translation), 1970, vol. 6, # 10, p. 2002 - 2007

  摘要：

  DOI：

文献信息

• Sulfated diglyceride derivatives, salts thereof, and processes for their preparation
  申请人：Rosen J. Milton

  公开号：US20060167298A1

  公开（公告）日：2006-07-27

  The present invention relates to novel sulfated derivatives of disubstituted glycerides, and to methods for their preparation. In some embodiments, the present invention provides compounds having the Formula Ia or Ib: wherein the constituent variables are as defined herein.

  本发明涉及新型磺酸化的二取代甘油酯衍生物，以及其制备方法。在某些实施例中，本发明提供具有化学式Ia或Ib的化合物： 其中组分变量如本文所定义。
• Preparation of Glycerol Carbonate Esters by using Hybrid Nafion-Silica Catalyst
  作者：María J. Climent、Avelino Corma、Sara Iborra、Sergio Martínez-Silvestre、Alexandra Velty

  DOI：10.1002/cssc.201300146

  日期：2013.7

  selectivity towards GCEs, were obtained using a Nafion–silica composite. A full reaction scheme has been established, and it has been demonstrated that an undesired competing reaction results in the generation of glycerol and esters derived from a secondary hydrolysis of the endocyclic ester group, which is attributed to water formed during the esterification reaction. The influence of temperature, substrate

  碳酸甘油酯（GCEs）是有价值的生物质衍生化合物，是通过在不存在溶剂的情况下，通过碳酸甘油酯和具有不同链长的长有机酸的直接酯化反应，并使用非均相催化剂（包括酸性有机树脂）制备的，沸石和杂化有机-无机酸。使用Nafion-二氧化硅复合材料在活性和对GCE的选择性方面获得了最佳结果。已经建立了完整的反应方案，并且已经证明不期望的竞争反应导致由内环酯基团的二次水解产生的甘油和酯的产生，这归因于在酯化反应期间形成的水。温度，底物比例，催化剂/底物比例，并且已经研究了溶剂的使用，并且在优化的反应条件下和使用适当的催化剂的情况下，有可能在98％的转化率下获得95％的目标产物选择性。结果表明，随着反应速率的增加，羧酸的直链烷基链中的碳原子数增加，反应速率降低。对甲苯磺酸和Nafion-二氧化硅纳米复合材料（Nafion SAC-13）催化剂。在将实验数据拟合到基于机理的动力学模型后，确定了Nafion
• Cardiolipin molecules and methods of synthesis
  申请人：Ahmad U. Moghis

  公开号：US20050266068A1

  公开（公告）日：2005-12-01

  The invention provides new synthetic routes for cardiolipin with different fatty acids and/or alkyl chains with varying chain length and also with or without unsaturation, particularly a short-chain cardiolipin. The methods comprise reacting a 1,2-O-sn-diacyl/1,2-O-sn-dialkyl glycerol or a 2-O-protected glycerol, with a phosphoramidite reagent or a phosphate triester to produce a protected cardiolipin, which is deprotected to prepare the short chain cardiolipin. The reaction schemes can be used to generate new variants of cardiolipin. The cardiolipin prepared by the present methods can be incorporated into liposomes, which can also include active agents such as hydrophobic or hydrophilic drugs. Such liposomes can be used to treat diseases or in diagnostic and/or analytical assays. Liposomes can also include ligands for targeting a particular cell type or specific tissue.

  本发明提供了一种合成不同脂肪酸和/或不同链长烷基的心磷脂的新合成路线，以及具有或不具有不饱和度，特别是一种短链心磷脂。该方法包括将1,2-O-sn-二酰基/1,2-O-sn-二烷基甘油或2-O-保护甘油与磷酸酰胺试剂或磷酸三酯反应以产生受保护的心磷脂，然后去保护以制备短链心磷脂。该反应方案可用于生成心磷脂的新变体。通过本方法制备的心磷脂可以被纳入到脂质体中，这些脂质体还可以包括疏水性或亲水性药物等活性剂。这样的脂质体可以用于治疗疾病或在诊断和/或分析检测中使用。脂质体还可以包括用于靶向特定细胞类型或特定组织的配体。
• Fatty Acid Phytyl Ester Synthesis in Chloroplasts of <i>Arabidopsis</i>
  作者：Felix Lippold、Katharina vom Dorp、Marion Abraham、Georg Hölzl、Vera Wewer、Jenny Lindberg Yilmaz、Ida Lager、Cyrille Montandon、Céline Besagni、Felix Kessler、Sten Stymne、Peter Dörmann

  DOI：10.1105/tpc.112.095588

  日期：2012.5

  During stress or senescence, thylakoid membranes in chloroplasts are disintegrated, and chlorophyll and galactolipid are broken down, resulting in the accumulation of toxic intermediates, i.e., tetrapyrroles, free phytol, and free fatty acids. Chlorophyll degradation has been studied in detail, but the catabolic pathways for phytol and fatty acids remain unclear. A large proportion of phytol and fatty acids is converted into fatty acid phytyl esters and triacylglycerol during stress or senescence in chloroplasts. We isolated two genes (PHYTYL ESTER SYNTHASE1 [PES1] and PES2) of the esterase/lipase/thioesterase family of acyltransferases from Arabidopsis thaliana that are involved in fatty acid phytyl ester synthesis in chloroplasts. The two proteins are highly expressed during senescence and nitrogen deprivation. Heterologous expression in yeast revealed that PES1 and PES2 have phytyl ester synthesis and diacylglycerol acyltransferase activities. The enzymes show broad substrate specificities and can employ acyl-CoAs, acyl carrier proteins, and galactolipids as acyl donors. Double mutant plants (pes1 pes2) grow normally but show reduced phytyl ester and triacylglycerol accumulation. These results demonstrate that PES1 and PES2 are involved in the deposition of free phytol and free fatty acids in the form of phytyl esters in chloroplasts, a process involved in maintaining the integrity of the photosynthetic membrane during abiotic stress and senescence.

  在压力或衰老期间，叶绿体中的类囊体膜会分解，叶绿素和半乳糖脂也会分解，导致有毒中间产物（即四吡咯、游离植物醇和游离脂肪酸）的积累。对叶绿素的降解进行了详细研究，但植物醇和脂肪酸的分解代谢途径仍不清楚。在压力或衰老期间，叶绿体中的大部分植物醇和脂肪酸会转化为脂肪酸植物酯和三酰甘油。我们从拟南芥中分离出酯酶/脂肪酶/硫酯酶家族中的两个基因（植物酯合成酶1 [PES1]和PES2），它们参与叶绿体中脂肪酸植物酯的合成。在衰老和氮缺乏期间，这两种蛋白质的表达量很高。在酵母中的异源表达表明，PES1和PES2具有植物酯合成和二酰甘油酰基转移酶活性。这些酶具有广泛的底物特异性，可以使用酰基-CoA、酰基载体蛋白和半乳糖脂作为酰基供体。双突变体植物（pes1 pes2）生长正常，但植物酯和三酰甘油的积累减少。这些结果表明，PES1和PES2参与游离植物醇和游离脂肪酸以植物酯的形式在叶绿体中的沉积，这一过程在非生物胁迫和衰老期间参与维持光合膜的完整性。
• Verwendung von Wirkstoffen, gewählt aus der Gruppe der 1,2-Diacylglycerole, zur Stärkung der Barrierefunktion der Haut
  申请人：Beiersdorf Aktiengesellschaft

  公开号：EP0995430A2

  公开（公告）日：2000-04-26

  Verwendung von Wirkstoffen, gewählt aus der Gruppe der 1,2-Diacylglycerole zur Stärkung der Barrierefunktion der Haut.

  使用选自 1,2-二乙酰甘油的活性成分来增强皮肤的屏障功能。