Fatty Acid Steryl, Stanyl, and Steroid Esters by Esterification and Transesterification in Vacuo Using <i>Candida rugosa</i> Lipase as Catalyst

Weber, Nikolaus; Weitkamp, Petra; Mukherjee, Kumar D.

doi:10.1021/jf000830w

Cited by 68 publications

(53 citation statements)

References 12 publications

(11 reference statements)

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“…Osanai (3) reported the synthesis of an oleic acid ester of cholesterol using lipase and organic hydrocarbon solvents such as cyclohexane, benzene, and toluene, whereas Shimada et al (4) reported the synthesis of a DHA ester of cholesterol in a two-phase medium containing 30% water. Furthermore, Weber et al (5)(6)(7) efficiently synthesized steryl esters by carrying out the enzymatic reaction under reduced pressure to remove the water and alcohol from the reaction system.…”

mentioning

confidence: 99%

Transesterification of phytosterol and edible oil by lipase powder at high temperature

Negishi

Hidaka

Takahashi

et al. 2003

J Americ Oil Chem Soc

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Phytosterol, which is hardly soluble in edible oil, was solubilized at a high concentration by converting it to FA esters by lipase-catalyzed transesterification at temperatures higher than 100°C using powdered Lipase QLM (Meito Sangyo Co., Ltd., Nagoya, Japan). Transesterification was conducted in sunflower oil containing 10% phytosterol, without adding water or solvent, at 100°C. The conversion rate was 97.1% after 7 h of reaction. The effect of temperature on the conversion rate was also examined. Maximum enzyme activity occurred in the 100-120°C range, and 20% of the maximum activity was retained even at 130°C. When the lipase was recovered by filtration and recycled for repeated reactions at 90°C, the half-life of lipase activity was 260 h. Thus, edible oils with nutritional value could be produced by blending the phytosterol-containing sunflower oil into other edible oils.Paper no. J10563 in JAOCS 80, 905-907 (September 2003). KEY WORDS:Edible oil, high temperature, lipase, phytosterol, phytosteryl ester, β-sitosterol, β-sitosteryl ester, thermostable, transesterification.Because of the nutritional advantages of phytosterols and the FA esters of phytosterols in the suppression of cholesterol absorption (1), various attempts have been made to develop phytosterol-containing edible oils. However, the m.p. of sterols are higher than 100°C, and thus they precipitate in edible oil. This is a critical drawback that prevents the commercialization of phytosterol on its own. Therefore, conversion to a corresponding FA ester, such as oleate, is considered desirable. Although FA esters of phytosterols can be synthesized by chemical reaction, the chemical method involves problems such as the formation of a 3,5-diene derivative as a side product and staining.To avoid these problems, an enzymatic method that uses lipase was developed (2). To synthesize FA esters of sterols using lipase, the reaction was carried out in organic solvent or in an oil/water two-phase medium to increase the solubility of the sterol in the oil substrate. Osanai (3) reported the synthesis of an oleic acid ester of cholesterol using lipase and organic hydrocarbon solvents such as cyclohexane, benzene, and toluene, whereas Shimada et al. (4) reported the synthesis of a DHA ester of cholesterol in a two-phase medium containing 30% water. Furthermore, Weber et al. (5-7) efficiently synthesized steryl esters by carrying out the enzymatic reaction under reduced pressure to remove the water and alcohol from the reaction system.However, in the future, the construction of a continuous reaction system will be required, as edible oils are manufactured in production line systems in practice. For that reason, it is desirable to construct a reaction system that requires no solvents and that contains procedures for loading and unloading reactants during the reaction. Therefore, it is preferable to construct a reaction system as simply as possible, which is advantageous from the safety standpoint as well.We previously reported on the practical production of tran...

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confidence: 99%

Transesterification of phytosterol and edible oil by lipase powder at high temperature

Negishi

Hidaka

Takahashi

et al. 2003

J Americ Oil Chem Soc

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“…Among various catalysts, pyridine, PB, TEA, NBS and DMAP are effective catalysts and widely used in various reactions. Lipase also has been used in organic media for the catalysis of esterification and transesterification reactions (Weber et al 2001;Yadav and Devi 2004). As shown in Table 1, MAXH with a DS rang of 0.35-0.94 were achieved at the catalysts concentration of 20 wt% (based on the dried xylan-rich hemicelluloses weight).…”

Section: Effect Of the Chemical Reaction Conditions On The Ds Of Maxhmentioning

confidence: 99%

Glycidyl methacrylate derivatized xylan-rich hemicelluloses: synthesis and characterizations

et al. 2012

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In this paper, a novel type of hemicellulosic derivative containing polymerizable double bonds (C=C) was synthesized by chemical reaction of xylan-rich hemicelluloses and glycidyl methacrylate (GMA) in dimethyl sulfoxide (DMSO) in presence of catalysts. The chemical structure, reaction mechanism, and rheological properties of the derivative were investigated by means of FT-IR, 1 H and 13 C-NMR, DEPT 135 NMR, GC-MS and rheometer. The influence of the reaction conditions including reaction time, temperature, catalysts, and the amount of reagents on the degree of substitution were investigated in detail. Results showed that the chemical reaction of xylan-rich hemicelluloses with GMA was transesterification, which resulted in direct attachment of methacrylate (MA) groups to xylan-rich hemicelluloses, instead of GMA. A maximum degree of substitution of 0.94 could be achieved under the optimum reaction condition (40°C, 1.8 equiv of GMA to per xylose unit, 36 h, 20 % DMAP). Results from rheological analysis indicated that the aqueous solutions of the methacrylated xylan-rich hemicelluloses (MAXH; 0.5, 1.0 and 2.0 wt%) exhibited typical shear-thinning behavior in the range of shear rates tested. The viscoelasticity of MAXH solutions increased with the increasing concentration and DS.

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“…2.8 Purity analysis and structure characterization 2.8.1 Thin layer chromatography (TLC) analysis [22] Products were diluted in the chloroform and spotted, compared with phytosterols and PUFA. Development was carried out in a petroleum ether (60-908C)/ether/acetic acid 90:10:1 v/v/v and the spots were visualized by iodine vapor and exposure in oven set at 1808C for 5 min.…”

Section: Solubility Of Sterol Ester Of Pufa In Vegetable Oilmentioning

confidence: 99%

Chemical synthesis of phytosterol esters of polyunsaturated fatty acids with ideal oxidative stability

Deng

Zhang

Huang

et al. 2011

Euro J Lipid Sci & Tech

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In this study, direct esterification of phytosterols with polyunsaturated fatty acid (PUFA) catalyzed by sodium bisulfate to produce sterol esters of PUFA was performed without organic solvent. Considering on both degree of esterification (DE) and oxidative stability, response surface methodology (RSM) was employed for modeling the phytosterol esters of PUFA production to obtain a food grade process. The optimal and mild reaction conditions were obtained as follows: mass ratio of PUFA:phytosterols ¼ 4:1; amount of catalyst: 3% of the raw materials weight; reaction temperature 1308C; reaction time 8 h. Under these conditions, the degree of esterification was up to 96%, GC, TLC, NMR and GC-MS results showed that purity of purified sterol ester was above 99%, and b-sitosterol linolenate account for about 88%. Sterol ester of PUFA possessed low peroxide value (PV) (0.96 meq/kg) and conjugated diene (CD) value (2.15 mmol/kg), and high oxidative induction period (OIP) (10.4 h). Addition amount of sterol ester of PUFA into soybean oil, rapeseed oil, and flaxseed oil below 1, 1, and 3%, respectively, could increase OIP of the vegetable oil. The primrose phytosterol esters of PUFA possessed very low melting point, crystallization temperature, and greater solubility in oils. All the characteristics favored the wide application of sterol ester of PUFA produced by the food grade process in different formulations of functional foods.

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Fatty Acid Steryl, Stanyl, and Steroid Esters by Esterification and Transesterification in Vacuo Using Candida rugosa Lipase as Catalyst

Cited by 68 publications

References 12 publications

Transesterification of phytosterol and edible oil by lipase powder at high temperature

Transesterification of phytosterol and edible oil by lipase powder at high temperature

Glycidyl methacrylate derivatized xylan-rich hemicelluloses: synthesis and characterizations

Chemical synthesis of phytosterol esters of polyunsaturated fatty acids with ideal oxidative stability

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