title: Efficient synthesis and characterization of ergosterol laurate in a solvent-free system.
abstract: Ergosterol and its derivatives have attracted much attention for a variety of health benefits, such as anti-inflammatory and antioxidant activities. However, ergosterol esters are advantageous because this compound has better solubility than the free ergosterol. In this work, ergosterol laurate was efficiently synthesized for the first time by direct esterification in a solvent-free system. The desired product was purified, characterized by Fourier transform infrared spectroscopy, mass spectrometry, and nuclear magnetic resonance, and finally confirmed to be ergosterol laurate. Meanwhile, the effect of various catalysts, catalyst dose, reaction temperature, substrate molar ratio, and reaction time were studied. Both the conversion of ergosterol and the selectivity of the desired product can reach above 89% under the selected conditions: sodium dodecyl sulfate + hydrochloric acid as the catalyst, 2:1 molar ratio of lauric acid/ergosterol, catalyst dose of 4% (w/w), 120 °C, and 2 h. The oil solubility of ergosterol and its laurate was also compared. The results showed that the solubility of ergosterol in oil was significantly improved by direct esterification with lauric acid, thus greatly facilitating the incorporation into a variety of oil-based systems.
authors.affiliation: School of Food and Biological Engineering, Jiangsu University , 301 Xuefu Road, Zhenjiang, Jiangsu 212013, People's Republic of China.
authors.forename: Wen-Sen
authors.initials: WS
authors.lastname: He
authors.forename: Ji
authors.initials: J
authors.lastname: Yin
authors.forename: Han-Shan
authors.initials: HS
authors.lastname: Xu
authors.forename: Qiu-Ying
authors.initials: QY
authors.lastname: Qian
authors.forename: Cheng-Sheng
authors.initials: CS
authors.lastname: Jia
authors.forename: Hai-Le
authors.initials: HL
authors.lastname: Ma
authors.forename: Biao
authors.initials: B
authors.lastname: Feng
mesh_terms: D002384:Catalysis; D004875:Ergosterol / Q000138:chemical synthesis* / Q000737:chemistry; D004951:Esterification; D004952:Esters / Q000737:chemistry; D007848:Laurates / Q000737:chemistry*; D007850:Lauric Acids / Q000737:chemistry
chemical_list: D004952:Esters; D007848:Laurates; D007850:Lauric Acids; C030358:lauric acid; D004875:Ergosterol
keywords: ergosterol; ergosterol laurate; esterification; oil solubility; solvent-free