A concise synthesis of β-sitosterol and other phytosterols

Hang, Jiliang; Dussault, Patrick H.

doi:10.1016/j.steroids.2010.05.016

Cited by 24 publications

(24 citation statements)

References 26 publications

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“…These peaks confirm the formation of ester links which resulted from the reaction between the hydroxyl group of soybean sterol and the carbonyl group of acetic anhydride. Hang and Dussault () similarly reported strong peaks at 1730 and 1247 cm −1 for campesterol acetic ester.…”

Section: Resultsmentioning

confidence: 90%

“…7, 2016 r Journal of Food Science C1631 acetic anhydride. Hang and Dussault (2010) similarly reported strong peaks at 1730 and 1247 cm −1 for campesterol acetic ester.…”

Section: Ftirmentioning

confidence: 87%

“…Chemical method has higher esterification rate and shorter reaction time than enzymatic method (Villeneuve and others ; Valange and others ; Robles‐Manuel and others ; Pan and others ). However, chemical esterification requires the use of catalysts including magnesium oxide, lanthanum oxide, zinc oxide, aluminum oxide, and aluminum triiodide (Valange and others ; Hang and Dussault ; Meng and others ; Robles‐Manuel and others ). Chemical esterification presents a major challenge, which is the difficulty in separating catalyst from the final products.…”

Section: Introductionmentioning

confidence: 99%

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Novel Synthesis of Phytosterol Ester from Soybean Sterol and Acetic Anhydride

Yang

Oyeyinka

2016

Journal of Food Science

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Phytosterols are important bioactive compounds which have several health benefits including reduction of serum cholesterol and preventing cardiovascular diseases. The most widely used method in the synthesis of its ester analogous form is the use of catalysts and solvents. These methods have been found to present some safety and health concern. In this paper, an alternative method of synthesizing phytosterol ester from soybean sterol and acetic anhydride was investigated. Process parameters such as mole ratio, temperature and time were optimized. The structure and physicochemical properties of phytosterol acetic ester were analyzed. By the use of gas chromatography, the mole ratio of soybean sterol and acetic anhydride needed for optimum esterification rate of 99.4% was 1:1 at 135 °C for 1.5 h. FTIR spectra confirmed the formation of phytosterol ester with strong absorption peaks at 1732 and 1250 cm(-1) , which corresponds to the stretching vibration of C=O and C-O-C, respectively. These peaks could be attributed to the formation of ester links which resulted from the reaction between the hydroxyl group of soybean sterol and the carbonyl group of acetic anhydride. This paper provides a better alternative to the synthesis of phytosterol ester without catalyst and solvent residues, which may have potential application in the food, health-care food, and pharmaceutical industries.

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Section: Resultsmentioning

confidence: 90%

“…7, 2016 r Journal of Food Science C1631 acetic anhydride. Hang and Dussault (2010) similarly reported strong peaks at 1730 and 1247 cm −1 for campesterol acetic ester.…”

Section: Ftirmentioning

confidence: 87%

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Novel Synthesis of Phytosterol Ester from Soybean Sterol and Acetic Anhydride

Yang

Oyeyinka

2016

Journal of Food Science

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“…Chemical synthesis shows advantageous, as it provides good conversion rate (CR), and high productivity, but it has several drawbacks too. For example, chemical esterification requires the use of catalysts including magnesium oxide, lanthanum oxide, zinc oxide, aluminum oxide, and aluminum triiodide (Hang & Dussault, 2010;Meng, Pan, & Yang, 2010;Robles-Manuel, Barrault, & Valange, 2011;Valange et al, 2007). The major challenge is the difficulty in separating catalyst from the final product, also the high temperature may lead to the production of byproduct.…”

Section: Introductionmentioning

confidence: 99%

In vitro bioaccessibility and physicochemical properties of phytosterol linoleic ester synthesized from soybean sterol and linoleic acid

Yang

Oyeyinka

et al. 2018

LWT

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Phytosterols are bioactive components capable of reducing cholesterol level in serum and reducing risk of arteriosclerosis. In this study, conditions for the synthesis of maximum yield of phytosterol linoleic ester (PLE) was optimized and the physicochemical properties and in vitro bioaccessibility of the PLE was assessed. Under the optimized condition of 1:1.1 mole ratio of phytosterol and linoleoyl chloride at 80 o C for 1.5h, the conversion rate of phytosterol reached 96.1%. Its solubility in oil increased 20 times, up to 33.8%. Also, peroxide value of PLE was much lower than linoleic acid (32.9 and 47.0 mmol/kg), which means better oxidative stability. Bioaccessibility of PLE was affected by time, concentration of bile extract, and dissolved medium. It was 4.93% alone, increased by 2.5times compare to phytosterol; or 53.46% in oil, under the condition of 40mg/mL bile extract for 120min. In conclusion, under the tested condition, phytosterol conversion rate, its solubility in oil and bioaccessibility were improved significantly. The method showed great potential in manufacture high quality and quantity of PLE.

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“…It is commercially available in preparative amounts only as mixtures with other phytosterols typically stigmasterol and campesterol (Hang and Dussault 2010). β-Sitosterol has been proven to be a safe, nontoxic, effective nutritional supplement and has amazing potential health benefits in many diverse applications including antibacterial activity (Sen et al, 2012).The antimicrobial activity (inhibitory test) of the isolated compound represented by diameter of zone of inhibition ranged between 20-35 mm against S. typhii and E.coli at varying concentrations (Table 2).…”

Section: Resultsmentioning

confidence: 99%

Beta-sitosterol with antimicrobial property from the stem bark of pomegranate (<i>Punica granatum</i> Linn)

Nweze¹,

Ibrahim²,

Ndukwe³

2019

Journal of Applied Sciences and Environmental Management

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The aim of this research was to isolate and characterize bioactive substances that may be responsible for the ethno medicinal uses of Punica granatum. Phytochemical constituents and characterization led to the isolation of Beta-Sitosterol from the hexane extract of the stem bark of the plant. The structure of the isolated compound was elucidated by spectra data including FTIR, 1D-and 2D-NMR. The compound was active against Salmonella typhi and Escherichia coli with zones of inhibition of 20 and 35 mm respectively which were appreciable with that of the standard. The values of minimum inhibitory concentration (MIC) were as low as 6.25 and 12.5 μg/ml against Salmonella typhi and Escherichia coli respectively.

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A concise synthesis of β-sitosterol and other phytosterols

Cited by 24 publications

References 26 publications

Novel Synthesis of Phytosterol Ester from Soybean Sterol and Acetic Anhydride

Novel Synthesis of Phytosterol Ester from Soybean Sterol and Acetic Anhydride

In vitro bioaccessibility and physicochemical properties of phytosterol linoleic ester synthesized from soybean sterol and linoleic acid

Beta-sitosterol with antimicrobial property from the stem bark of pomegranate (<i>Punica granatum</i> Linn)

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