title: Efficient solvent-free synthesis of phytostanyl esters in the presence of acid-surfactant-combined catalyst.
abstract: An efficient approach based on the synthesis of phytostanyl esters with an acid-surfactant-combined catalyst in a solvent-free system was developed. The effect of catalyst dose, substrate molar ratio, reaction temperature, and acyl donor was considered. The reaction conditions were further optimized by response surface methodology, and a high yield of phytostanyl laurate (>92%) was obtained under optimum conditions: 3.17:1 molar ratio of lauric acid to plant stanols, 4.01% catalyst dose (w/w), 119 °C, and 4.1 h. FT-IR, MS, and NMR were adopted to confirm the chemical structure of phytostanyl laurate. Meanwhile, the physiochemical properties of different phytostanyl esters were investigated. Compared with phytostanols, the prepared phytostanyl esters had much lower melting temperature and higher oil solubility. There was no obvious difference in melting and solidification properties between sunflower oil with phytostanyl laurate (<5%) or oleate (<10%) and the original sunflower oil, suggesting that the esterification of phytostanols greatly facilitated their corporation into oil-based foods.
authors.affiliation: State Key Laboratory of Food Science and Technology, School of Food Science and Technology, Jiangnan University, 1800 Lihu Road, Wuxi 214122, Jiangsu, China.
authors.forename: Wen-Sen
authors.initials: WS
authors.lastname: He
authors.forename: Yuan
authors.initials: Y
authors.lastname: Ma
authors.forename: Xiao-Xia
authors.initials: XX
authors.lastname: Pan
authors.forename: Jing-Jing
authors.initials: JJ
authors.lastname: Li
authors.forename: Mei-Gui
authors.initials: MG
authors.lastname: Wang
authors.forename: Ye-Bo
authors.initials: YB
authors.lastname: Yang
authors.forename: Cheng-Sheng
authors.initials: CS
authors.lastname: Jia
authors.forename: Xiao-Ming
authors.initials: XM
authors.lastname: Zhang
authors.forename: Biao
authors.initials: B
authors.lastname: Feng
mesh_terms: D002384:Catalysis; D002851:Chromatography, High Pressure Liquid; D004951:Esterification; D004952:Esters / Q000138:chemical synthesis* / Q000737:chemistry; D007848:Laurates / Q000138:chemical synthesis*; D007850:Lauric Acids / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D015394:Molecular Structure; D010840:Phytosterols / Q000138:chemical synthesis*; D010938:Plant Oils / Q000737:chemistry; D012995:Solubility; D012997:Solvents; D017550:Spectroscopy, Fourier Transform Infrared; D000074242:Sunflower Oil; D013501:Surface-Active Agents / Q000737:chemistry*; D013696:Temperature
chemical_list: D004952:Esters; D007848:Laurates; D007850:Lauric Acids; D010840:Phytosterols; D010938:Plant Oils; D012997:Solvents; D000074242:Sunflower Oil; D013501:Surface-Active Agents; C030358:lauric acid