Synthesis of plant-derived cholesterol from bisnoralcohol

Xing-Zi Li; Chen-Chen Li; Cheng-Yu Jiang; Zhi-Liang Jing; Xiang-Zhong Gu; Hao-Jie Ni; Wen-Wei Qiu

doi:10.1016/j.steroids.2022.108967

Synthesis of plant-derived cholesterol from bisnoralcohol

Steroids. 2022 Feb:178:108967. doi: 10.1016/j.steroids.2022.108967. Epub 2022 Jan 24.

Authors

Xing-Zi Li¹, Chen-Chen Li², Cheng-Yu Jiang³, Zhi-Liang Jing¹, Xiang-Zhong Gu⁴, Hao-Jie Ni⁵, Wen-Wei Qiu⁶

Affiliations

¹ Shanghai Engineering Research Center of Molecular Therapeutics and New Drug Development, School of Chemistry and Chemical Engineering, East China Normal University, Shanghai 200241, China.
² Shanghai Engineering Research Center of Molecular Therapeutics and New Drug Development, School of Chemistry and Chemical Engineering, East China Normal University, Shanghai 200241, China; ECNU-JIAERKE Pharm. Steroids Green Manufacturing Laboratory, East China Normal University, Shanghai 200241, China.
³ Department of Research and Development, Jiangsu Jiaerke Pharmaceuticals Group Co., Ltd., Zhenglu Town, Changzhou 213111, China.
⁴ Department of Research and Development, Jiangsu Jiaerke Pharmaceuticals Group Co., Ltd., Zhenglu Town, Changzhou 213111, China; ECNU-JIAERKE Pharm. Steroids Green Manufacturing Laboratory, East China Normal University, Shanghai 200241, China.
⁵ ECNU-JIAERKE Pharm. Steroids Green Manufacturing Laboratory, East China Normal University, Shanghai 200241, China.
⁶ Shanghai Engineering Research Center of Molecular Therapeutics and New Drug Development, School of Chemistry and Chemical Engineering, East China Normal University, Shanghai 200241, China; ECNU-JIAERKE Pharm. Steroids Green Manufacturing Laboratory, East China Normal University, Shanghai 200241, China. Electronic address: wwqiu@chem.ecnu.edu.cn.

PMID: 35085676
DOI: 10.1016/j.steroids.2022.108967

Abstract

Currently, the market demand of the non-animal-derived cholesterol is increasing. A novel synthetic route of producing cholesterol was developed through multiple reactions from plant-sourced and commercially available bisnoralcohol (BA). The key reaction conditions, including solvents, reaction temperatures, bases and reducing agents of the route were investigated and optimized. In this straightforward synthetic pathway of cholesterol, most of the reaction steps possess high conversions with average yields of 94%, and the overall yield is up to 74% (5 steps) from the BA. The epicholesterol and were also synthesized. This promising route offers economical and efficient strategies for potential large-scale production of plant-derived cholesterol.

Keywords: Bisnoralcohol; Cholesterol; Synthesis.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Cholesterol*
Plants*
Solvents

Substances

Solvents
Cholesterol