sucrose-6,6'-di-O-laurate | 20881-06-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 糖脂
• 英文名称: sucrose-6,6'-di-O-laurate
• 英文别名: 6,6'-di-O-lauroylsucrose；Sucrose 6,6'-dilaurate；[(2R,3S,4S,5R,6R)-6-[(2S,3S,4S,5R)-5-(dodecanoyloxymethyl)-3,4-dihydroxy-2-(hydroxymethyl)oxolan-2-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methyl dodecanoate
• CAS: 20881-06-5
• 化学式: C₃₆H₆₆O₁₃
• 分子量: 706.912
• InChiKey: ITWBEULHMPBCFM-SDBGFSJOSA-N

物化性质

• 沸点：
  801.5±65.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  49
• 可旋转键数：
  29
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  202
• 氢给体数：
  6
• 氢受体数：
  13

反应信息

• 作为产物：
  描述：

  月桂酸乙烯酯 、 6-O-sucrose monolaurate 在 lipase Novozym 435 from Candida antarctica 作用下， 以 丙酮 为溶剂， 反应 24.0h， 以86%的产率得到sucrose-6,6'-di-O-laurate
  参考文献：
  名称：

  Lipase-Catalysed Selective Synthesis of Sucrose Mixed Diesters

  摘要：

  研究了脂肪酶催化的蔗糖酯化反应与活化和非活化酰基供体反应的选择性。使用 Novozym 435 脂肪酶，可以获得高转化率和高选择性的蔗糖脂肪酸二酯和混合脂肪酸甲基丙烯酸二酯。

  DOI：

  10.1055/s-2001-11436

文献信息

• Shape Dependence in the Formation of Condensed Phases Exhibited by Disubstituted Sucrose Esters
  作者：Valérie Molinier、Paul J. J. Kouwer、Juliette Fitremann、Alain Bouchu、Grahame Mackenzie、Yves Queneau、John W. Goodby

  DOI：10.1002/chem.200600368

  日期：2007.2.12

  We report on the self-organizing properties of sucrose esters that are di-(1',6', 1',6, and 6,6')-substituted with aliphatic chains of identical or different chain lengths and levels of saturation. For the materials possessing two saturated aliphatic chains, the compounds exhibited thermotropic lamellar smectic A phases. A remarkable new phase transition was observed for the di-octadecanoyl homologue

  我们报告了被相同或不同链长和饱和度的脂族链二（1'，6'，1'，6和6,6'）取代的蔗糖酯的自组织特性。对于具有两个饱和脂族链的材料，该化合物表现出热致性层状近晶A相。对于二十八烷酰基同系物观察到了显着的新相变，其中一个层列A相转变为另一层，层间距连续变化，但相关长度不连续变化。较长的顺式不饱和链的引入导致链的横截面积相对于蔗糖头基增加，因此观察到柱状相。
• Improved synthesis of sucrose fatty acid monoesters under ultrasonic irradiation
  作者：Dan Huang、Xue Jiang、Hao Zhu、Xiaorong Fu、Kangrong Zhong、Weidong Gao

  DOI：10.1016/j.ultsonch.2009.08.009

  日期：2010.2

  Sucrose fatty acid esters were synthesized by the transesterification of sucrose with aliphatic esters under ultrasound irradiation in good yield (73%). The optimum reaction conditions for the transesterification reaction include a molar ratio of sucrose to fatty acid ethyl ester of 2:1 and the use of a 13%mol anhydrous K(2)CO(3) catalyst. The optimum reaction temperature was set at 70 degrees C, the

  蔗糖脂肪酸酯是通过在超声辐射下将蔗糖与脂肪族酯进行酯交换而合成的，收率很高（73％）。酯交换反应的最佳反应条件包括蔗糖与脂肪酸乙酯的摩尔比为2：1，并使用13％摩尔的无水K（2）CO（3）催化剂。最佳反应温度设定为70℃，最佳反应时间为2h，最佳反应压力为11kPa。该反应具有优异的单酯选择性。通过快速柱色谱法在硅胶上纯化的产物中的单酯（6-单酯+ 6'-单酯）比例高达92-95％，6-单酯/ 6'-单酯的比例为2.1-2.7，并且通过HPLC-MS，NMR和IR鉴定蔗糖单酯。
• Sucrose esterification under Mitsunobu conditions: evidence for the formation of 6-O-acyl-3′,6′-anhydrosucrose besides mono and diesters of fatty acids
  作者：Valérie Molinier、Juliette Fitremann、Alain Bouchu、Yves Queneau

  DOI：10.1016/j.tetasy.2004.04.021

  日期：2004.6

  A series of sucrose monoesters and homogeneous or mixed diesters, which have various chain lengths and saturation levels, were prepared under Mitsunobu conditions with good regioselectivity. Among the anhydro derivatives arising from competitive intramotecular etherification, 3,6'-anhydrosucrose 6-O-monoesters, which have never been reported, were identified. (C) 2004 Elsevier Ltd. All rights reserved.
• Lipase-Catalysed Selective Synthesis of Sucrose Mixed Diesters
  作者：Pierre Potier、Alain Bouchu、Gérard Descotes、Yves Queneau

  DOI：10.1055/s-2001-11436

  日期：——

  The selectivity of the esterification of sucrose was studied in the case of lipase-catalysed reactions with activated and non-activated acyl donors. Using the lipase Novozym 435, sucrose fatty acid diesters and mixed fatty acid methacrylic acid diesters were obtained in high conversion and selectivity.

  研究了脂肪酶催化的蔗糖酯化反应与活化和非活化酰基供体反应的选择性。使用 Novozym 435 脂肪酶，可以获得高转化率和高选择性的蔗糖脂肪酸二酯和混合脂肪酸甲基丙烯酸二酯。