Docosanoic acid 2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester | 228263-82-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: Docosanoic acid 2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester
• 英文别名: (2,2-dimethyl-1,3-dioxolan-4-yl)methyl docosanoate
• CAS: 228263-82-9
• 化学式: C₂₈H₅₄O₄
• 分子量: 454.734
• InChiKey: LSDAROVCHHZPHR-UHFFFAOYSA-N

物化性质

• 沸点：
  515.3±30.0 °C(Predicted)
• 密度：
  0.915±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.5
• 重原子数：
  32.0
• 可旋转键数：
  22.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  44.76
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  Docosanoic acid 2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester 在 Amberlyst 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 12.0h， 以35.6 mg的产率得到二十二烷酸甘油单酯
  参考文献：
  名称：

  Synthesis of glycerolipids containing simple linear acyl chains or aromatic rings and evaluation of their Mincle signaling activity

  摘要：

  合成的甘油酯衍生物具有简单的烷基链，可刺激与先天性免疫系统相关的 Mincle 介导的信号检测。

  DOI：

  10.1039/c8cc07322h
• 作为产物：
  描述：

  二十二酸 在 吡啶 、 氯化亚砜 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 2.0h， 生成 Docosanoic acid 2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester
  参考文献：
  名称：

  Synthesis of glycerolipids containing simple linear acyl chains or aromatic rings and evaluation of their Mincle signaling activity

  摘要：

  合成的甘油酯衍生物具有简单的烷基链，可刺激与先天性免疫系统相关的 Mincle 介导的信号检测。

  DOI：

  10.1039/c8cc07322h

文献信息

• Biochemical characterization of the PHARC-associated serine hydrolase ABHD12 reveals its preference for very-long-chain lipids
  作者：Alaumy Joshi、Minhaj Shaikh、Shubham Singh、Abinaya Rajendran、Amol Mhetre、Siddhesh S. Kamat

  DOI：10.1074/jbc.ra118.005640

  日期：2018.11

  Polyneuropathy, hearing loss, ataxia, retinitis pigmentosa, and cataract (PHARC) is a rare genetic human neurological disorder caused by null mutations to the Abhd12 gene, which encodes the integral membrane serine hydrolase enzyme ABHD12. Although the role that ABHD12 plays in PHARC is understood, the thorough biochemical characterization of ABHD12 is lacking. Here, we report the facile synthesis of mono-1-(fatty)acyl-glycerol lipids of varying chain lengths and unsaturation and use this lipid substrate library to biochemically characterize recombinant mammalian ABHD12. The substrate profiling study for ABHD12 suggested that this enzyme requires glycosylation for optimal activity and that it has a strong preference for very-long-chain lipid substrates. We further validated this substrate profile against brain membrane lysates generated from WT and ABHD12 knockout mice. Finally, using cellular organelle fractionation and immunofluorescence assays, we show that mammalian ABHD12 is enriched on the endoplasmic reticulum membrane, where most of the very-long-chain fatty acids are biosynthesized in cells. Taken together, our findings provide a biochemical explanation for why very-long-chain lipids (such as lysophosphatidylserine lipids) accumulate in the brains of ABHD12 knockout mice, which is a murine model of PHARC.
• Study of the Effect of DATEM. 1. Influence of Fatty Acid Chain Length on Rheology and Baking
  作者：Peter Köhler、Werner Grosch

  DOI：10.1021/jf980891i

  日期：1999.5.1

  To answer the question of which fatty acid residue is the most effective, diacetyltartaric esters of monoglycerides (DATEMs) with fatty acids of chain lengths 6:0-20:0 were synthesized. The activity of synthesized DATEMs and commercial DATEM products was studied by means of rheological methods and a microscale baking test with 10 g of flour. Variation of the acyl residue from 6:0 to 22:0 showed that stearic acid (18:0) had the best effect on the baking activity of DATEM (loaf volume increased by 62%). DATEMs containing unsaturated fatty acids (18:1, 18:2) or DATEMs produced from diacylglycerols instead of monoacylglycerols showed a slight increase of the loaf volumes. A slight effect of DATEM on the rheology of dough was observed. However, much greater was the effect on the gluten isolated from doughs prepared with DATEM. The resistance of gluten to extension was increased after the addition of increasing amounts of DATEM (0.1-0.5%). Within the series of DATEMs derived from the homologous series of monoacylglycerols the product based on glycerol monostearate (18:0) showed a maximum increase of the gluten resistance.
• Synthesis of glycerolipids containing simple linear acyl chains or aromatic rings and evaluation of their Mincle signaling activity
  作者：Takanori Matsumaru、Risa Ikeno、Yusuke Shuchi、Toshiki Iwamatsu、Takashi Tadokoro、Sho Yamasaki、Yukari Fujimoto、Atsushi Furukawa、Katsumi Maenaka

  DOI：10.1039/c8cc07322h

  日期：——

  The synthesized glycerolipid derivatives possessing simple alkyl chains can stimulate a Mincle-mediated signaling assay relevant for the innate immune system.

  合成的甘油酯衍生物具有简单的烷基链，可刺激与先天性免疫系统相关的 Mincle 介导的信号检测。