Highly efficient synthesis of 4,4-dimethylsterol oleates using acyl chloride method through esterification

Liangliang Xie; Tao Zhang; Emad Karrar; Dan Xie; Liyou Zheng; Jun Jin; Xingguo Wang; Qingzhe Jin

doi:10.1016/j.foodchem.2021.130140

Highly efficient synthesis of 4,4-dimethylsterol oleates using acyl chloride method through esterification

Food Chem. 2021 Dec 1:364:130140. doi: 10.1016/j.foodchem.2021.130140. Epub 2021 May 18.

Authors

Liangliang Xie¹, Tao Zhang², Emad Karrar², Dan Xie³, Liyou Zheng³, Jun Jin², Xingguo Wang², Qingzhe Jin⁴

Affiliations

¹ Collaborative Innovation Center of Food Safety and Quality Control in Jiangsu Province, National Engineering Research Center for Functional Food, School of Food Science and Technology, Jiangnan University, Wuxi 214122, China; School of Biological and Food Engineering, Anhui Polytechnic University, Wuhu 241000, China.
² Collaborative Innovation Center of Food Safety and Quality Control in Jiangsu Province, National Engineering Research Center for Functional Food, School of Food Science and Technology, Jiangnan University, Wuxi 214122, China.
³ School of Biological and Food Engineering, Anhui Polytechnic University, Wuhu 241000, China.
⁴ Collaborative Innovation Center of Food Safety and Quality Control in Jiangsu Province, National Engineering Research Center for Functional Food, School of Food Science and Technology, Jiangnan University, Wuxi 214122, China. Electronic address: jqzwx12@163.com.

PMID: 34175623
DOI: 10.1016/j.foodchem.2021.130140

Abstract

In this study, the 4,4-dimethylsterol oleates were efficiently synthesized through esterification of 4,4-dimethylsterols and oleoyl chloride. The impact of reaction parameters on the 4,4-dimethylsterol conversion were investigated. The 4,4-dimethylsterol conversion increased with pyridine dosage, molar ratio of oleoyl chloride to 4,4-dimethylsterols, and temperature. The highest conversion of 99.27% was obtained with molar ratio of 1.1:1 at 313 K for 60 min. A second-order kinetic model describing acyl chloride esterification featuring high correlation coefficients was established. Arrhenius-Van't Hoff plot suggested activation energy and pre-exponential factor were 15.54 kJ mol^-1 and 1.78 × 10³ L mol^-1 min^-1, respectively. The molecular structure of 4,4-dimethylsterol oleates were finally identified by attenuated total reflection fourier transform infrared spectroscopy (ATR-FTIR), ultra-performance liquid chromatography system coupled with quadrupole time of flight mass spectrometry (UPLC-Q-TOF-MS), and nuclear magnetic resonance (NMR).

Keywords: 4,4-dimethylsterol oleates; Esterification; Kinetic model; Oleoyl chloride.

MeSH terms

Chlorides*
Chromatography, High Pressure Liquid
Chromatography, Liquid
Esterification
Mass Spectrometry
Oleic Acid*

Substances

Chlorides
Oleic Acid