The enzymatic synthesis of glucosylmyristate as a reaction model for general considerations on ‘sugar esters’ production

Cauglia, Fabio; Canepa, Paolo

doi:10.1016/j.biortech.2007.01.036

Cited by 66 publications

(42 citation statements)

References 7 publications

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“…Usually, increasing temperature can increase the solubility of sucrose in fatty acid methyl ester and intensify the esterification reaction, but high temperature would induce caramelisation, which is a parallel and undesirable reaction (Jiang et al ., ). The sucrose can be hydrolysed into fructose and glucose with the existence of water (Cauglia & Canepa, ; Pito et al ., ). Caramelisation always starts from the dehydration of sucrose, fructose or glucose, if the temperature is high enough.…”

Section: Introductionmentioning

confidence: 99%

Heterogeneous base catalytic transesterification synthesis of sucrose ester and parallel reaction control

Zhao

Chang

Jin

et al. 2013

Int J of Food Sci Tech

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The equilibrium solubility of sucrose in methyl stearate, methyl oleate and methyl laurate with or without the addition of surfactants was investigated. The side reactions, pyrolysis of the sucrose, glucose and fructose, are also discussed through studying their data of differential thermal analysis and thermal gravimetric analysis. Results show that the solubilities of sucrose in methyl esters of fatty acids range from 0.01 g/100 g to 0.21 g/100 g in a surfactant-free system with the temperature range of 40-140°C. The addition of surfactants increased the sucrose solubility in the fatty acid esters. Under the strict anhydrous conditions, the soap concentration can be controlled at a very low level. With the increase in the temperature, sucrose began to decrease in weight at 225 AE 5°C, glucose began to decrease in weight at 85 AE 5°C, and fructose began to decrease in weight at 170 AE 5°C.

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Section: Introductionmentioning

confidence: 99%

Heterogeneous base catalytic transesterification synthesis of sucrose ester and parallel reaction control

Zhao

Chang

Jin

et al. 2013

Int J of Food Sci Tech

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“…Catalytic hydrogenation of 5 on Pd/C in THF solution afforded pure 6 in quantitative yield after catalyst filtration and solvent evaporation at room temperature. Compound 6 was used as a key intermediate for the synthesis of derivatives 7a -7h , which were obtained by the Knoevenagel-Doebner reaction of 6 with a series of aldehydes in the presence of pyridine [9,10,11,12,13,14,15]. The derivatives were characterized by IR, 1 H-NMR, and MS spectroscopy.…”

Section: Resultsmentioning

confidence: 99%

Synthesis and Biological Activity of trans-Tiliroside Derivatives as Potent Anti-Diabetic Agents

et al. 2010

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A set of novel trans-tiliroside derivatives were synthesized. The structures of the derivatives were identified by their IR, 1H-NMR, and MS spectra analysis. Their anti-diabetic activities were evaluated on the insulin resistant (IR) HepG2 cell model. As a result, compounds 7a, 7c, 7h, and trans-tiliroside exhibited significant glucose consumption-enhancing effects in IR-HepG2 cells compared with the positive control (metformin). This research provides useful clues for further design and discovery of anti-diabetic agents.

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“…Water activity or water content influences not only the enzyme conformational stability in organic solvents but also the thermodynamics of the equilibrated reaction. 23,48,49 Chamouleau and co-workers 49 studied the effect of water activity and water content on the enzymatic synthesis of sugar esters with C. antarctica. As a w values rise, both the conversion and initial reaction rate decrease.…”

Section: Synthesis Of Sucrose Esters In Organic Mediamentioning

confidence: 99%

Enzyme‐catalyzed regioselective synthesis of sucrose‐based esters

Shi

Lǐ

Chu

2011

J of Chemical Tech & Biotech

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Sucrose-based esters are nonionic biosurfactants, which can be synthesized from the enzyme-catalyzed esterification/transesterification of sucrose. The multi-hydroxyl groups of sucrose and the immiscibility of sucrose with the acyl donors are the main bottlenecks in obtaining highly regioselective sucrose-based esters. In this mini-review, the effects of reaction conditions such as biocatalysts, design of solvent systems used as reaction media, modification and denaturation of substrates, and coupling with external auxiliary physical fields such as microwave irradiation and ultrasonic waves on the yield of sucrose esters and regioselectivity of products are highlighted. The existing problems in the field of enzymatic synthesis of sucrose esters as well as its future perspectives were pointed out.

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The enzymatic synthesis of glucosylmyristate as a reaction model for general considerations on ‘sugar esters’ production

Cited by 66 publications

References 7 publications

Heterogeneous base catalytic transesterification synthesis of sucrose ester and parallel reaction control

Heterogeneous base catalytic transesterification synthesis of sucrose ester and parallel reaction control

Synthesis and Biological Activity of trans-Tiliroside Derivatives as Potent Anti-Diabetic Agents

Enzyme‐catalyzed regioselective synthesis of sucrose‐based esters

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