Synthesis and crystallization purification of phytosterol esters for food industry application

Abstract

This work aimed to investigate the process parameters of phytosterol esters (PE) synthesis catalyzed by copper oxide-nano hydroxyapatite (CuO-NHAP) and the crystallization purification technology. CuO-NHAP was prepared. The synthesis of PE catalyzed by CuO-NHAP was performed. After Response Surface Methodology optimization, the optimal process parameters were as follows: reaction temperature, 180 o C; reaction time, 6.3 h; acid-alcohol molar ratio, 1.9; catalyst amount, 1.05%. Under these conditions, the esterification rate of phytosterols was 99.8%. The crystallization purification technology of esterification product was explored. The optimal crystallization conditions were as follows: crystallization solvent, octanoic acid; crystallization temperature, 0 o C; solvent-product molar ratio, 4: 1; crystallization time, 10 h. Under these conditions, the unreacted fatty acids and other impurities were affectively removed, and the PE purity in purification product was 98.2%. These synthesis and crystallization purification technologies of PE are relatively green, safe, efficient and economic, and have the potential to be applied to the industrial preparation of PE product.

Conjugates of 1,3‐ and 1,2‐Acylglycerols with Stigmasterol: Synthesis, NMR Characterization, and Impact on Lipid Bilayers

“…In the first step 1,2-O-isopropylidene-3-stigmasterylcarbonoyl-sn-glycerol (12) was achieved in high yield (92 %) by coupling of (S)-solketal (11) and StigCF in the presence of DMAP followed by purification of crude product by flash chromatography. Similarly, conjugation of (S)-solketal (11) with StigHS by typical Steglich esterification in the presence of DCC and DMAP resulted in 1,2-O-isopropylidene-3-stigmasterylsuccinoyl-snglycerol (16) in 68 % yield.…”

“…[11,12] Following that way, various PS derivatives have been synthesized, i.a. esters with long-chain fatty acids, [13][14][15][16][17] conjugated linoleic acid (CLA), [18] phenolic acids, [19][20][21][22][23][24] lipoic acid [25] as well as conjugates with catechin [26] and glycerophosphocholine. [27] Liposomes formed with the use of the letter conjugate were used as carriers of biologically active compounds: doxorubicin and amphotericin B.…”