Efficient Solvent-Free Synthesis of Phytostanyl Esters in the Presence of Acid-Surfactant-Combined Catalyst

He, Wen‐Sen; Ma, Yuan; Pan, Xiaoxia; Li, Jingjing; Wang, Mei-Gui; Yang, Yebo; Jia, Chengsheng; Zhang, Xiaoming; Feng, Bo

doi:10.1021/jf302958g

Cited by 27 publications

(24 citation statements)

References 31 publications

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“…In 2012, He et al prepared fatty phytostanyl laurate, a cholesterol-lowering food additive, by the esterification reaction of phytosterols with lauric acid in the presence of DS and HCl. [30] The authors reported a yield as high as 92 % after optimization of the reaction parameters. Later on, the same team extended the preparation of phytostanyl laurate to copper and cerium dodecyl sulfates (i.e., [Cu(DS) 2 ] and [Ce(DS) 3 ], respectively) as Lewis acidic surfactant-combined catalysts, which showed in all cases promising activities.…”

Section: Amphiphilic Acid/base Catalystsmentioning

confidence: 99%

Pickering Interfacial Catalysis for Biphasic Systems: From Emulsion Design to Green Reactions

Leclercq²,

et al. 2015

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Pickering emulsions are surfactant-free dispersions of two immiscible fluids that are kinetically stabilized by colloidal particles. For ecological reasons, these systems have undergone a resurgence of interest to mitigate the use of synthetic surfactants and solvents. Moreover, the use of colloidal particles as stabilizers provides emulsions with original properties compared to surfactant-stabilized emulsions, microemulsions, and micellar systems. Despite these specific advantages, the application of Pickering emulsions to catalysis has been rarely explored. This Minireview describes very recent examples of hybrid and composite amphiphilic materials for the design of interfacial catalysts in Pickering emulsions with special emphasis on their assets and challenges for industrially relevant biphasic reactions in fine chemistry, biofuel upgrading, and depollution.

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Section: Amphiphilic Acid/base Catalystsmentioning

confidence: 99%

Pickering Interfacial Catalysis for Biphasic Systems: From Emulsion Design to Green Reactions

Leclercq²,

et al. 2015

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“…4a, the conversion of octacosanol reached 90.9 ± 3.6 % at 1:1 molar ratio of octacosanol to linoleic acid. Generally speaking, the esterification reactions were reversible, the increase of the amount of one substrate could promote the occurrence of the esterification reaction and shift the reaction equilibrium toward the products [25]. However, the conversion rate was not significantly increased with the increase of the molar ratio of octacosanol to octacosanol linoleate from 1:1 to 1:1.5 (P > 0.05).…”

Section: Effect Of Substrate Molar Ratio and Reaction Timementioning

confidence: 90%

Efficient Synthesis of Octacosanol Linoleate Catalyzed by Ionic Liquid and Its Structure Characterization

Qiao

et al. 2016

J Americ Oil Chem Soc

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IntroductionPolicosanols are a kind of primary aliphatic long-chain alcohol with chain lengths varying from 24 to 34 carbons, and octacosanol is one of the major components of policosanols with 28 carbons [1,2]. The most common sources of policosanols are sugar cane, bees wax, wheat germ, rice bran, sorghum kernel and sunflower seed [3][4][5]. Policosanols are also found in the leaves, fruits, nuts, and seeds of many foods [6].In recent years, policosanols have attracted much attention due to their potential beneficial effects for human health. Policosanols provided various physiological effects in the prevention or treatment of cardiovascular diseases and dermatological diseases [7,8]. Policosanols acted as a cholesterol-lowering agent by inhibiting endogenous cholesterol biosynthesis and enhancing low density lipoprotein (LDL) catabolism [7]. Daily intake of 5-20 mg policosanols decreased the LDL level by 19-31 % and total cholesterol (TC) concentration by 13-23 %, increased high density lipoprotein (HDL) cholesterol level in the range of 8-29 % [9, 10]. Daily supplement of 40 mg policosanol was also found to be effective in lowering the serum triglyceride concentration [9]. Moreover, previous studies reported that policosanols decreased endothelial damage, platelet aggregation and the development of foam cells [7,11]. Octacosanol was considered to be the major active policosanols responsible for efficacy since it was present in the largest quantity [6,12]. Octacosanol improved oxygen usage by strengthening the heart, keeping low LDL and high HDL levels, thereby maintaining healthy heart function [9,13].Currently, policosanols including octacosanol are mainly produced by saponification of a by-product from the dewaxing process. And policosanols are commercially Abstract Octacosanol, as the major active policosanol, has attracted much attention due to the potential beneficial effects for human health. However, free octacosanol has a high melting point, poor oil solubility and low bioavailability, which greatly restricts its practical application. In this study, we report a highly efficient method for an ionic liquids (IL)-catalyzed synthesis of octacosanol ester by direct esterification with linoleic acid. The synthesized product was purified, subsequently characterized by FT-IR, MS and NMR and finally confirmed to be octacosanol linoleate. The reaction parameters were investigated and the conversion reached 91.3 ± 4.8 % under the optimum conditions: IL 1-butylsulfonate-3-methylimidazolium hydrogen sulfate ([BSO 3 HMim][HSO 4 ]) as catalyst, IL dose 1.5 % (related to the mass of both reactants), 1:1 molar ratio of octacosanol to linoleic acid, 80 °C, and 1 h. The melting point and oil solubility of octacosanol were greatly improved by esterification with linoleic acid, facilitating the incorporation into a variety of oil-based systems.

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“…However, the practical use of the sterols in other foods has been greatly limited by their poor solubilities [1,91]. Esterification of ergosterol is, therefore, performed to make it fat-soluble and easy to incorporate into food products [91,92].…”

Section: Oxidation Resistance Of Lanosterol and Ergosterolmentioning

confidence: 99%

Characteristics of Specialty Natural Micronutrients in Certain Oilseeds and Oils: Plastochromanol‐8, Resveratrol, 5‐Hydroxytryptamine Phenylpropanoid Amides, Lanosterol, Ergosterol and Cyclolinopeptides

Jin

Sheraliev

Xie

et al. 2015

J Americ Oil Chem Soc

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The current concern for health has raised the importance of natural micronutrients in edible oils and fats. Different from common micronutrients, e.g., tocopherols, tocotrienols, stigmasterol and sitosterol, new and emerging specialty micronutrients, such as plastochromanol‐8, resveratrol, phenylpropanoid amides of 5‐hydroxytryptamine, lanosterol, ergosterol and cyclolinopeptides, are becoming increasingly popular among health‐conscious people. The first three are phenolic compounds, the forth and fifth sterols, and sixth a peptide. These micronutrients are usually present in certain oils or oilseed‐related byproducts, including rapeseed, peanut, flaxseed, tea seed, and camellia oils, and safflower seed cakes, all of which are the highly valuable products of the lipid industry in China nowadays. The first object of this review is to discuss the characteristics of the micronutrients, mainly including their varieties, structures, and sources. Second, the antioxidant activities and indicative functions for oil quality were also analyzed in detail. Third, refining techniques, breeding programs and extraction methods are suggested. Suitable modification treatments of certain micronutrients are also advocated to make them easy to incorporate in other foods.

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Efficient Solvent-Free Synthesis of Phytostanyl Esters in the Presence of Acid-Surfactant-Combined Catalyst

Cited by 27 publications

References 31 publications

Pickering Interfacial Catalysis for Biphasic Systems: From Emulsion Design to Green Reactions

Pickering Interfacial Catalysis for Biphasic Systems: From Emulsion Design to Green Reactions

Efficient Synthesis of Octacosanol Linoleate Catalyzed by Ionic Liquid and Its Structure Characterization

Characteristics of Specialty Natural Micronutrients in Certain Oilseeds and Oils: Plastochromanol‐8, Resveratrol, 5‐Hydroxytryptamine Phenylpropanoid Amides, Lanosterol, Ergosterol and Cyclolinopeptides

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