dihexadecyl 2,2'-thiodiacetate

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: dihexadecyl 2,2'-thiodiacetate
• 英文别名: Hexadecyl 2-(2-hexadecoxy-2-oxoethyl)sulfanylacetate
• 化学式: C₃₆H₇₀O₄S
• 分子量: 599.015
• InChiKey: YAEYEIPKNZEQKE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  16.2
• 重原子数：
  41
• 可旋转键数：
  36
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  77.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1-十六烷醇 、 硫代二乙酸 在 Novozym 435 作用下， 80.0 ℃ 、80.0 kPa 条件下， 反应 72.0h， 生成 dihexadecyl 2,2'-thiodiacetate
  参考文献：
  名称：

  Dialkyl 3,3‘-Thiodipropionate and Dialkyl 2,2‘-Thiodiacetate Antioxidants by Lipase-Catalyzed Esterification and Transesterification

  摘要：

  Medium- and long-chain dialkyl 3,3'-thiodipropionate antioxiclants such as dioctyl 3,3'-thiodipropionate, didodecyl 3,3'-thiodipropionate, clihexadecyl 3,3'-thiodipropionate, and di-(cis-9-octadecenyl) 3,3'-thiodipropionate were prepared in high yield by lipase-catalyzed esterification and transesterification of 3,3'-thiodipropionic acid and its dimethyl ester, respectively, with the corresponding medium- or long-chain 1-alkanols, i.e., 1-octanol, 1-dodecanol, 1-hexadecanol, and cis-9-octadecen-1-ol, in vacuo (80 kPa) at moderate temperatures (60-80 degrees C) without solvents. Immobilized lipase B from Candida antarctica (Novozym 435) was the most active biocatalyst for the preparation of medium- and longchain dialkyl 3,3'-thiodipropionates showing enzyme activities up to 1489 units/g, whereas the immobilized lipases from Phizomucor miehei (Lipozyme RM IM) and Thermomyces lanuginosus (Lipozyme TL IM) were by far less active (similar to 10 enzyme units/g). Maximum conversions to dialkyl 3,3'-thiodipropionates were as high as 92-98% after 4 h of reaction time. Similarly, dihexadecyl 2,2'-thiodiacetate was prepared in high yield using 2,2'-thiodiacetic acid or diethyl 2,2'-thiodiacetate and 1-hexaclecanol as the starting materials and Novozym 435 as the biocatalyst.

  DOI：

  10.1021/jf0530502

文献信息

• Dialkyl 3,3‘-Thiodipropionate and Dialkyl 2,2‘-Thiodiacetate Antioxidants by Lipase-Catalyzed Esterification and Transesterification
  作者：Nikolaus Weber、Erika Klein、Klaus Vosmann

  DOI：10.1021/jf0530502

  日期：2006.4.1

  Medium- and long-chain dialkyl 3,3'-thiodipropionate antioxiclants such as dioctyl 3,3'-thiodipropionate, didodecyl 3,3'-thiodipropionate, clihexadecyl 3,3'-thiodipropionate, and di-(cis-9-octadecenyl) 3,3'-thiodipropionate were prepared in high yield by lipase-catalyzed esterification and transesterification of 3,3'-thiodipropionic acid and its dimethyl ester, respectively, with the corresponding medium- or long-chain 1-alkanols, i.e., 1-octanol, 1-dodecanol, 1-hexadecanol, and cis-9-octadecen-1-ol, in vacuo (80 kPa) at moderate temperatures (60-80 degrees C) without solvents. Immobilized lipase B from Candida antarctica (Novozym 435) was the most active biocatalyst for the preparation of medium- and longchain dialkyl 3,3'-thiodipropionates showing enzyme activities up to 1489 units/g, whereas the immobilized lipases from Phizomucor miehei (Lipozyme RM IM) and Thermomyces lanuginosus (Lipozyme TL IM) were by far less active (similar to 10 enzyme units/g). Maximum conversions to dialkyl 3,3'-thiodipropionates were as high as 92-98% after 4 h of reaction time. Similarly, dihexadecyl 2,2'-thiodiacetate was prepared in high yield using 2,2'-thiodiacetic acid or diethyl 2,2'-thiodiacetate and 1-hexaclecanol as the starting materials and Novozym 435 as the biocatalyst.