1',6'-O-didodecanoylsucrose | 335281-15-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1',6'-O-didodecanoylsucrose
• 英文别名: 1',6'-Di-O-lauryl sucrose；Sucrose 1,6-dilaurate；[(2R,3S,4S,5S)-5-(dodecanoyloxymethyl)-3,4-dihydroxy-5-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxolan-2-yl]methyl dodecanoate
• CAS: 335281-15-7
• 化学式: C₃₆H₆₆O₁₃
• 分子量: 706.912
• InChiKey: RWTLOOVGCAXGBZ-SDBGFSJOSA-N

物化性质

• 沸点：
  801.5±65.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(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

• 作为反应物：
  描述：

  3,4,5-tris(benzyloxy)benzoyl chloride 、 1',6'-O-didodecanoylsucrose 在 palladium on activated charcoal 4-二甲氨基吡啶 、 三乙胺 、 氢气 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 [(2R,3R,4S,5R,6R)-6-[(2S,3S,4R,5R)-2,5-bis(dodecanoyloxymethyl)-3,4-bis[(3,4,5-trihydroxybenzoyl)oxy]oxolan-2-yl]oxy-3,4,5-tris[(3,4,5-trihydroxybenzoyl)oxy]oxan-2-yl]methyl 3,4,5-trihydroxybenzoate
  参考文献：
  名称：

  Gallic Esters of Sucrose as Efficient Radical Scavengers in Lipid Peroxidation

  摘要：

  Three tests of increasing complexity were used to assess the antioxidant activity of five synthetic gallic esters of sucrose bearing 3, 6, 7, or 8 galloyl units. In addition, two of these compounds had 1 or 2 hydrocarbon (C10-C12) acyl chains. Reaction with the DPPH radical led to the evaluation of the number of radicals trapped per galloyl unit n (3-4), as well as the apparent second-order rate constant for H atom donation k (1200-1500/M/s). These results indicated similar contribution and reactivity of all the galloyl units. Inhibition of the AAPH-initiated peroxidation of linoleic acid in a micellar medium confirmed the additive contribution of the galloyl units, whereas the presence of the hydrocarbon acyl chains had no influence, These results suggest an inhibition of initiation at high antioxidant levels and an underlying prooxidant effect of the galloyl radicals at low concentrations. Finally, LDL peroxidation was inhibited in proportion to the number of galloyl units, in agreement with the preceding tests.

  DOI：

  10.1021/jf011683k
• 作为产物：
  描述：

  月桂酸乙烯酯 、 mono-1'-O-lauroylsucrose 在 lipase Novozym 435 from Candida antarctica 作用下， 以 丙酮 为溶剂， 反应 24.0h， 以80%的产率得到1',6'-O-didodecanoylsucrose
  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

• 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。
• Gallic Esters of Sucrose as Efficient Radical Scavengers in Lipid Peroxidation
  作者：Claire Dufour、Eric da Silva、Pierre Potier、Yves Queneau、Olivier Dangles

  DOI：10.1021/jf011683k

  日期：2002.6.1

  Three tests of increasing complexity were used to assess the antioxidant activity of five synthetic gallic esters of sucrose bearing 3, 6, 7, or 8 galloyl units. In addition, two of these compounds had 1 or 2 hydrocarbon (C10-C12) acyl chains. Reaction with the DPPH radical led to the evaluation of the number of radicals trapped per galloyl unit n (3-4), as well as the apparent second-order rate constant for H atom donation k (1200-1500/M/s). These results indicated similar contribution and reactivity of all the galloyl units. Inhibition of the AAPH-initiated peroxidation of linoleic acid in a micellar medium confirmed the additive contribution of the galloyl units, whereas the presence of the hydrocarbon acyl chains had no influence, These results suggest an inhibition of initiation at high antioxidant levels and an underlying prooxidant effect of the galloyl radicals at low concentrations. Finally, LDL peroxidation was inhibited in proportion to the number of galloyl units, in agreement with the preceding tests.