1-棕榈酰-2-月桂酰-锡-甘油 | 89648-22-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 甘油脂
• 中文名称: 1-棕榈酰-2-月桂酰-锡-甘油
• 英文名称: 1-palmitoyl-2-lauroyl-sn-glycerol
• 英文别名: 2-dodecanoyl-1-hexadecanoyl-sn-glycerol；[(2S)-2-dodecanoyloxy-3-hydroxypropyl] hexadecanoate
• CAS: 89648-22-6
• 化学式: C₃₁H₆₀O₅
• 分子量: 512.814
• InChiKey: XBAHYRKXTRBDBF-LJAQVGFWSA-N

物化性质

• 熔点：
  53-55 °C
• 沸点：
  577.2±17.0 °C(Predicted)
• 密度：
  0.940±0.06 g/cm3(Predicted)
• 物理描述：
  Solid

计算性质

• 辛醇/水分配系数(LogP)：
  11.9
• 重原子数：
  36
• 可旋转键数：
  30
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-棕榈酰-2-月桂酰-锡-甘油 在 三乙胺 作用下， 以 乙腈 、 苯 为溶剂， 反应 32.0h， 生成 1-棕榈酰-2-月桂酰基卵磷脂
  参考文献：
  名称：

  A New Approach to the Stereospecific Synthesis of Phospholipids. The Use of l-Glyceric Acid for the Preparation of Diacylglycerols, Phosphatidylcholines, and Related Derivatives

  摘要：

  A new stereospecific synthesis of phospholipid derivatives of 1,2-diacyl-sn-glycerols is reported. The synthesis is based on (I) the use of L-glyceric acid as the stereocenter for construction of the optically active phospholipid molecule, (2) preparation of 3-triphenylmethyl-sn-glycerol as the key intermediate for sequential introduction of the primary and secondary acyl functions leading to the chiral diglycerides, and (3) elaboration of the sn-3-phosphodiester headgroup via phosphorylation using 2-chloro-2-oxo-1,3,2-dioxaphospholane, followed by ring opening of the five-membered phosphorus heterocycle with trimethylamine, ammonia, as well as oxygen and sulfur nucleophiles. The sequence has been shown to be suitable for the preparation of both symmetric and mixed-chain diacylglycerols with saturated and unsaturated acyl substituents. Phospholipid headgroups including phosphocholine, phosphoethanolamine, phosphoethanol, and phosphoethylthioacetate functions have been prepared. Application of the method to the synthesis of functionalized phosphatidylcholines has also been demonstrated by incorporating spectroscopically active spin-labeled and fluorescent reporter groups via postsynthetic derivatization of chain terminal w-aminoalkyl functions of the acyl substituents of the compounds. The synthetic methods developed have a great deal of flexibility, providing convenient routes to a wide range of structurally variable phospholipids for physicochemical, enzymological, and cell-biological studies.

  DOI：

  10.1021/jo990414e
• 作为产物：
  描述：

  3-O-benzyl-2-dodecanoyl-1-hexadecanoyl-sn-glycerol 在 palladium 10% on activated carbon 、 氢气 作用下， 以 四氢呋喃 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 16.0h， 以74%的产率得到1-棕榈酰-2-月桂酰-锡-甘油
  参考文献：
  名称：

  对映纯ABC型三酰基甘油的合成

  摘要：

  十二种具有三种不同脂肪酸的ABC型对映体纯结构化三酰甘油（TAGs）的合成是通过从（S）-缩酮开始的六步化学酶促方法进行描述的。八个TAG具有位于sn -1和sn -2位置的两个不同的饱和脂肪酰基，在甘油骨架的其余sn -3位置具有不饱和脂肪酰基，而其余​​四个具有两个不同的饱和酰基在终端SN -1和SN -3位置与所述的不饱和酰基SN-2位置。前一组是通过六步化学酶法合成的，涉及高度区域选择性的固定化念珠菌南极脂肪酶。第二组是通过类似的六步法制备的，该方法需要两个独立的脂肪酶步骤。强烈要求此类对映纯TAG作为对油脂中完整TAG进行对映特异性分析的标准。

  DOI：

  10.1016/j.tet.2019.130813

文献信息

• Synthesis of enantiopure ABC-type triacylglycerols
  作者：Haraldur G. Gudmundsson、Kaisa M. Linderborg、Heikki Kallio、Baoru Yang、Gudmundur G. Haraldsson

  DOI：10.1016/j.tet.2019.130813

  日期：2020.1

  the TAGs possess two different saturated fatty acyl groups located in the sn-1 and sn-2 positions with an unsaturated fatty acyl group in the remaining sn-3 position of the glycerol skeleton, whereas the remaining four possess two different saturated acyl groups in the terminal sn-1 and sn-3 positions with an unsaturated acyl group in the sn-2 position. The former group was synthesised by a six-step

  十二种具有三种不同脂肪酸的ABC型对映体纯结构化三酰甘油（TAGs）的合成是通过从（S）-缩酮开始的六步化学酶促方法进行描述的。八个TAG具有位于sn -1和sn -2位置的两个不同的饱和脂肪酰基，在甘油骨架的其余sn -3位置具有不饱和脂肪酰基，而其余​​四个具有两个不同的饱和酰基在终端SN -1和SN -3位置与所述的不饱和酰基SN-2位置。前一组是通过六步化学酶法合成的，涉及高度区域选择性的固定化念珠菌南极脂肪酶。第二组是通过类似的六步法制备的，该方法需要两个独立的脂肪酶步骤。强烈要求此类对映纯TAG作为对油脂中完整TAG进行对映特异性分析的标准。
• A New Approach to the Stereospecific Synthesis of Phospholipids. The Use of <scp>l</scp>-Glyceric Acid for the Preparation of Diacylglycerols, Phosphatidylcholines, and Related Derivatives
  作者：Farzaneh S. Roodsari、Dongpei Wu、Gregory S. Pum、Joseph Hajdu

  DOI：10.1021/jo990414e

  日期：1999.10.1

  A new stereospecific synthesis of phospholipid derivatives of 1,2-diacyl-sn-glycerols is reported. The synthesis is based on (I) the use of L-glyceric acid as the stereocenter for construction of the optically active phospholipid molecule, (2) preparation of 3-triphenylmethyl-sn-glycerol as the key intermediate for sequential introduction of the primary and secondary acyl functions leading to the chiral diglycerides, and (3) elaboration of the sn-3-phosphodiester headgroup via phosphorylation using 2-chloro-2-oxo-1,3,2-dioxaphospholane, followed by ring opening of the five-membered phosphorus heterocycle with trimethylamine, ammonia, as well as oxygen and sulfur nucleophiles. The sequence has been shown to be suitable for the preparation of both symmetric and mixed-chain diacylglycerols with saturated and unsaturated acyl substituents. Phospholipid headgroups including phosphocholine, phosphoethanolamine, phosphoethanol, and phosphoethylthioacetate functions have been prepared. Application of the method to the synthesis of functionalized phosphatidylcholines has also been demonstrated by incorporating spectroscopically active spin-labeled and fluorescent reporter groups via postsynthetic derivatization of chain terminal w-aminoalkyl functions of the acyl substituents of the compounds. The synthetic methods developed have a great deal of flexibility, providing convenient routes to a wide range of structurally variable phospholipids for physicochemical, enzymological, and cell-biological studies.