6'-O-palmitoylsucrose | 24516-45-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6'-O-palmitoylsucrose
• 英文别名: sucrose monopalmitate；Sucrose, 6'-palmitate；[(2R,3S,4S,5S)-3,4-dihydroxy-5-(hydroxymethyl)-5-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxolan-2-yl]methyl hexadecanoate
• CAS: 24516-45-8
• 化学式: C₂₈H₅₂O₁₂
• 分子量: 580.714
• InChiKey: DZPKXFNXNJJENH-ZRVLSRDKSA-N

物化性质

• 沸点：
  748.5±60.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  40
• 可旋转键数：
  21
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  196
• 氢给体数：
  7
• 氢受体数：
  12

反应信息

• 作为产物：
  描述：

  2,1':4,6-di-O-isopropylidene sucrose 在 tetrafluoroboric acid 、 Novozym 435 作用下， 以 甲苯 、 乙腈 为溶剂， 反应 56.0h， 生成 6'-O-palmitoylsucrose
  参考文献：
  名称：

  Application of lipases to the regioselective synthesis of sucrose fatty acid monoesters

  摘要：

  摘要 在有机溶剂和无溶剂条件下，通过脂肪酶催化蔗糖乙醛与脂肪酸的酯化反应，开发了一种 6′-O-酰基蔗糖单酯的区域选择性合成方法。用水溶液酸水解异亚丙基后，产品的总产率为 20-27%。所使用酶的严格选择性还使得制备单酯部分成为可能，该部分高度富含 6-O-酰基蔗糖。这是通过脂肪酶催化蔗糖单酯在丙-2-醇中的酯交换反应实现的，蔗糖单酯是用传统化学方法制备的。在去除酯交换产物（蔗糖和脂肪酸异丙酯）并在硅胶上进行柱层析后，得到的单酯产物中含有 80% 的单一 Regioisomer（6-O-acyl sucrose）。

  DOI：

  10.1007/bf02523514

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。
• Self-Organizing Properties of Monosubstituted Sucrose Fatty Acid Esters: The Effects of Chain Length and Unsaturation
  作者：Valérie Molinier、Paul J. J. Kouwer、Juliette Fitremann、Alain Bouchu、Grahame Mackenzie、Yves Queneau、John W. Goodby

  DOI：10.1002/chem.200500773

  日期：2006.4.24

  Three families of mono-substituted sucrose fatty acid esters were prepared by enzymatic and classical synthetic procedures, and their self-assembly and self-organizational properties were investigated by thermal polarised light microscopy, differential scanning calorimetry and X-ray diffraction. The properties were evaluated as a function of the fatty acid chain length. For the lower homologues of the

  通过酶促和经典合成方法制备了三族单取代蔗糖脂肪酸酯，并通过热偏振光显微镜，差示扫描量热法和X射线衍射研究了它们的自组装和自组织性质。评估性能作为脂肪酸链长的函数。对于系列的较低同系物，发现了柱状液晶堆叠结构，而对于较高的同系物，则以层状相为主。提出了一种柱状堆积排列的模型，该模型由分子的独特排列组成，这可能导致在色谱柱的疏水内部和亲水外部之间形成多个内部离子通道。
• 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.
• Application of lipases to the regioselective synthesis of sucrose fatty acid monoesters
  作者：Douglas B. Sarney、Mark J. Barnard、David A. MacManus、Evgeny N. Vulfson

  DOI：10.1007/bf02523514

  日期：1996.11

  A regioselective synthesis of 6′‐O‐acyl sucrose monoesters has been developed through the lipase‐catalyzed esterification of sucrose acetals with fatty acids in both organic solvents and under solvent‐free conditions. The products were obtained in overall yields of 20–27% after hydrolysis of the isopropylidene groups with aqueous acids. The strict selectivity of the enzymes used also enabled the preparation of a monoester fraction that was highly enriched in 6‐O‐acyl sucrose. This was accomplished by lipase‐catalyzed transesterification of sucrose monoesters, prepared by conventional chemical methods, in propan‐2‐ol. After removal of the transesterification products (sucrose and fatty acid isopropyl esters) and column chromatography on silica gel, the obtained monoester product contained 80% of the single regioisomer, 6‐O‐acyl sucrose.

  摘要 在有机溶剂和无溶剂条件下，通过脂肪酶催化蔗糖乙醛与脂肪酸的酯化反应，开发了一种 6′-O-酰基蔗糖单酯的区域选择性合成方法。用水溶液酸水解异亚丙基后，产品的总产率为 20-27%。所使用酶的严格选择性还使得制备单酯部分成为可能，该部分高度富含 6-O-酰基蔗糖。这是通过脂肪酶催化蔗糖单酯在丙-2-醇中的酯交换反应实现的，蔗糖单酯是用传统化学方法制备的。在去除酯交换产物（蔗糖和脂肪酸异丙酯）并在硅胶上进行柱层析后，得到的单酯产物中含有 80% 的单一 Regioisomer（6-O-acyl sucrose）。