1,6-di-O-caproyl-α-D-psicofuranose | 1067195-41-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,6-di-O-caproyl-α-D-psicofuranose
• 英文别名: [(2R,3S,4R,5S)-5-(decanoyloxymethyl)-3,4,5-trihydroxyoxolan-2-yl]methyl decanoate
• CAS: 1067195-41-8
• 化学式: C₂₆H₄₈O₈
• 分子量: 488.662
• InChiKey: HNIFZUCWKMWKSF-MYCYEZBNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  34
• 可旋转键数：
  22
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  123
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  乙烯基癸酸 、 D-psicofuranose 在 Candida antarctica lipase immobilized on a macroporous acrylic resin 作用下， 以 四氢呋喃 为溶剂， 反应 48.0h， 生成 1,6-di-O-caproyl-α-D-psicofuranose 、 1,6-di-O-caproyl-β-D-psicofuranose
  参考文献：
  名称：

  脂肪酶催化的d-蔗糖脂肪酸二酯的合成及其乳化活性

  摘要：

  AbstractThe diesterification of d‐psicose (the C‐3 epimer of d‐fructose) with fatty acid vinyl esters of selected acyl chain lengths (C8, C10, and C12) was successfully carried out using Candida antarctica lipase (Novozym 435) at 45 °C for 24 h to give the 1,6‐diacyl‐d‐psicofuranoses with a high regioselectivity in good yields (83–90%). These diesters of d‐psicose have hydrophilic‐lipophilic balance (HLB) values (6.5–8.2) similar to HLB values of monoglyceride compounds which constitute the largest single type of emulsifiers employed by the food industry. Ability of the d‐psicose diesters to stabilize oil‐in‐water emulsions and the weight‐averaged oil‐droplet diameter in the emulsions was evaluated in this study. Emulsion stability of oil droplets stabilized by d‐psicose dicaprylate (0.3%, w/v in oil phase) was comparable to d‐fructose dicaprylate (0.2%, w/v). It was further confirmed that the d‐psicose diesters exhibited an emulsification activity depending on the chain length of fatty acid; d‐psicose dicaprate showed better emulsion stability than the other diesters.

  DOI：

  10.1007/s11746-008-1242-x

文献信息

• Lipase-Catalyzed Synthesis of d-Psicose Fatty Acid Diesters and their Emulsification Activities
  作者：Ghanwa Afach、Yasuhiro Kawanami、Nopparat Cheetangdee、Kazuhiro Fukada、Ken Izumori

  DOI：10.1007/s11746-008-1242-x

  日期：2008.8

  AbstractThe diesterification of d‐psicose (the C‐3 epimer of d‐fructose) with fatty acid vinyl esters of selected acyl chain lengths (C8, C10, and C12) was successfully carried out using Candida antarctica lipase (Novozym 435) at 45 °C for 24 h to give the 1,6‐diacyl‐d‐psicofuranoses with a high regioselectivity in good yields (83–90%). These diesters of d‐psicose have hydrophilic‐lipophilic balance (HLB) values (6.5–8.2) similar to HLB values of monoglyceride compounds which constitute the largest single type of emulsifiers employed by the food industry. Ability of the d‐psicose diesters to stabilize oil‐in‐water emulsions and the weight‐averaged oil‐droplet diameter in the emulsions was evaluated in this study. Emulsion stability of oil droplets stabilized by d‐psicose dicaprylate (0.3%, w/v in oil phase) was comparable to d‐fructose dicaprylate (0.2%, w/v). It was further confirmed that the d‐psicose diesters exhibited an emulsification activity depending on the chain length of fatty acid; d‐psicose dicaprate showed better emulsion stability than the other diesters.