Solvent-free synthesis of phytosterol linoleic acid esters at low temperature

Liu, Wei; Xiao, Bing; Wang, Xiaoping; Chen, Jingnan; Yang, Guolong

doi:10.1039/d1ra00798j

Cited by 15 publications

(20 citation statements)

References 30 publications

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“…The catalytic mechanism of DBSA was related to reverse micellar catalysis (Liu et al ., 2021). The polar end of fatty acid COOH was mainly distributed inside the reverse micelles, while the hydrophobic part was outside the reverse micelles.…”

Section: Resultsmentioning

confidence: 99%

Microwave‐assisted catalytic synthesis of phytosterol esters

Zhang

et al. 2022

Int J of Food Sci Tech

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A low‐temperature reaction is of considerable importance in avoiding the degradation of phytosterol esters caused by high temperatures. In this study, an efficient method under mild conditions was developed to synthesise phytosterol esters by using microwave‐assisted catalyst dodecyl benzene sulphonic acid (DBSA). The phytosterol conversion reached 94.27% under the optimal conditions: oleic acid to phytosterol molar ratio of 2.5:1, catalyst dosage of 20% (mol%) and reaction temperature of 60°C for 60 min. Fourier transform infrared (FTIR) spectroscopy was applied to determine the structure of phytosterol oleates. Moreover, a second‐order kinetic model describing phytosterols esterification exhibited an adequate agreement with the experimental data. Microwave irradiation achieved the reduction of energy barrier (Ea = 29.17 kJ mol−1) in comparison with conventional heating (Ea = 49.22 kJ mol−1). This study suggests that microwave‐assisted catalyst DBSA is a reliable and efficient method for the production of high‐quality phytosterol esters.

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Section: Resultsmentioning

confidence: 99%

Microwave‐assisted catalytic synthesis of phytosterol esters

Zhang

et al. 2022

Int J of Food Sci Tech

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“…Through formation of emulsion of DBSA, esterification can take place smoothly at such mild temperature (40 • C) without removing the side-product water by special treatments (e.g., azeotropic distillation). During DBSA-catalyzed esterification, auto-isolation of water is the most important driving force of esterification [20].…”

Section: Mechanism Of Wax Esters Synthesis With Dbsa Catalystmentioning

confidence: 99%

Low-Temperature Esterification to Produce Oleic Acid-Based Wax Esters Catalyzed by 4-Dodecylbenzenesulfonic Acid

Li¹,

Liu²,

Yang³

2021

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Synthesized oleic acid-based wax esters (e.g., cetyl oleate), which can replace spermaceti oil or jojoba oil, have been widely used in the cosmetic, pharmaceutical and other industries. In this work, 4-dodecylbenzenesulfonic acid (DBSA) has been successfully used as an efficient catalyst to synthesize oleic acid-based wax esters through esterification at 40 °C under solvent-free conditions. A 93.6% conversion rate of cetyl alcohol was obtained under optimal conditions: 10 mol% DBSA, a molar ratio of 1.3:1 oleic acid to alcohol, a reaction temperature 40 °C and a reaction time of 4 h. The effect of water content on esterification was investigated, and it was found that the inhibitory effect of water decreased significantly with increasing temperature. Moreover, DBSA-catalyzed esterification could be applied in the production of various oleic acid-based wax esters and excellent conversion (>90%) to esters was obtained under such mild conditions. DBSA-catalyzed low-temperature esterification is an efficient method for the production of liquid wax esters.

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“…Among these, the esterification of PS has been confirmed to be one of the most successful techniques to improve its solubility or compatibility in the oil phase. [3][4][5] However, the consumption of esterified PS inevitably leads to a high intake of oils or lipids, therefore increasing the risk to health. Thus, the development of low-fat formulations of PSs is still an ongoing subject in the field, including formulation of PSs in emulsions, [6][7][8] spray-drying microencapsulation with arabic gum and maltodextrin, 9,10 liposomes made with soy phospholipids, 11 and more recently by fabrication of protein-based nanoparticles.…”

Section: Introductionmentioning

confidence: 99%

Soy proteins as vehicles for enhanced bioaccessibility and cholesterol‐lowering activity of phytosterols

Liu

Chen

et al. 2022

J Sci Food Agric

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BACKGROUND The formulation of phytosterol (PS)‐enriched functional foods has attracted increasing interest in the recent years, owing to its potential health effects. However, the poor solubility and bioavailability greatly limit PS application in this regard. This study investigated whether soy protein isolate (SPI) could effectively perform as a nanocarrier for improving the water solubility, bioaccessibility, and cholesterol‐lowering activity of PSs. RESULTS In this work, we fabricated SPI–PS nanocomplexes, which not only can enhance the stability and bioaccessibility of PS, but also improve the cholesterol‐lowering ability of SPI. This improvement was mainly due to the formation of protein‐active substance complexes, through hydrophobic interactions. The complexation with PSs resulted in formation of nanosized particles with greater sizes, lower ζ‐potential, and higher surface hydrophobicity. The encapsulation efficiency, loading amount, and solubility of PS were closely related to the applied PS concentration in the mixed dispersions, and the maximal PS solubility in the aqueous phase reached about 1.63 mg mL−1 at the highest PS concentration (2.0 mg mL−1). The PS molecules in the nanocomplexes were mainly present in the amorphous form. The enhanced in vitro cholesterol‐lowering activity of PS nanocomplexes relative to free PS seemed to be closely related to its higher bioaccessibility. CONCLUSION The findings are of relevance for the development of food‐grade PS ingredients suitable for the formulations of PS‐enriched functional foods. © 2022 Society of Chemical Industry.

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Solvent-free synthesis of phytosterol linoleic acid esters at low temperature

Abstract: Herein, we have developed a simple chemical method toward efficient preparation of phytosterol linoleic acid esters through esterification at very mild temperature (60 °C) using 4-dodecylbenzenesulfonic acid (DBSA) as the catalyst.

Cited by 15 publications

References 30 publications

Microwave‐assisted catalytic synthesis of phytosterol esters

Microwave‐assisted catalytic synthesis of phytosterol esters

Low-Temperature Esterification to Produce Oleic Acid-Based Wax Esters Catalyzed by 4-Dodecylbenzenesulfonic Acid

Soy proteins as vehicles for enhanced bioaccessibility and cholesterol‐lowering activity of phytosterols

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