Study of Vitamin Ester Synthesis by Lipase-Catalyzed Transesterification in Organic Media

Maugard, Thierry; Tudella, Joana; Legoy, Marie‐Dominique

doi:10.1021/bp000034a

Cited by 43 publications

(16 citation statements)

References 8 publications

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“…Due to the enzyme specificity and to the reduced process temperature required by enzymatic transformations, the lipasecatalyzed synthesis of these esters in low-water media presents significant advantages over the conventional chemical methods, namely, lower energy consumption, simplified downstream treatment, and reduced byproducts formation (3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(16). The latter feature is of critical importance when thermolabile fatty acids/ esters are processed.…”

Section: Introductionmentioning

confidence: 99%

Lipase-Catalyzed Transformations for the Synthesis of Butyl Lactate: A Comparison between Esterification and Transesterification

Pirozzi

Greco

2006

Biotechnol. Prog.

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The alpha-hydroxy esters are increasingly employed in cosmetic, food, and pharmaceutical formulations as they determine reduced skin-irritant effects in comparison with the respective acids, offering similar hygroscopic, emulsifying, and exfoliating properties. The enzymatic synthesis of lactate esters in nonaqueous systems was studied as regards the influence of the critical process parameters, to enable a comparison between the most commonly used synthetic routes, namely, esterification and transesterification. The experimental results showed that the direct esterification of lactic acid with butanol may be limited by the reduced lipase stability in the presence of the acid (substrate) and of the water (product), in particular when solvent-free media are used. The stability of the enzyme is further reduced as polar solvents are required as a result of the polarity of the lactic acid. Therefore, the use of the lactic acid as substrate is of practical interest only when the acid is significantly cheaper in comparison with its short-chain esters. If this is not the case, the transesterification of the ethyl lactate with butanol is to be preferred for the higher flexibility in the choice of the experimental conditions, the operability of solvent-free systems, and the simplicity of the product removal assembly.

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Section: Introductionmentioning

confidence: 99%

Lipase-Catalyzed Transformations for the Synthesis of Butyl Lactate: A Comparison between Esterification and Transesterification

Pirozzi

Greco

2006

Biotechnol. Prog.

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“…In 1990, Enomoto et al (4) filed a patent on the esterification in organic solvents, and esterfications in t-amyl alcohol were reported by Humeau et al (5) in 1995. Since then, not only saturated FA have been used, but also various unsaturated FA (6)(7)(8) as well as of phenyl butyric acid (9) and methyl lactate (10). These syntheses have typically reached yields below 50% unless activated acyl donors or a large excess of the FA was used.…”

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confidence: 99%

Antioxidative properties and enzymatic synthesis of ascorbyl FA esters

Viklund

Alander²,

Hult

2003

J Americ Oil Chem Soc

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Efficient synthesis of unsaturated FA esters of ascorbic acid is possible with only a small excess of one of the reactants in t-amyl alcohol using Candida antarctica lipase as biocatalyst. Using free acids, we obtained yields that were comparable to yields reached using vinyl-activated acyl donors (71, 80, and 86% yields of esters with FA excesses of 1:1, 1:1.5, and 1:2, respectively). As very low water activity is needed to achieve sufficiently high yields of product, molecular sieves were used to improve the ascorbyl ester yields. Ascorbyl oleate is more amorphous and has a much lower m.p. and lower enthalpy of fusion than ascorbyl palmitate. This leads to a higher solubility of ascorbyl oleate in oil, resulting in an increased antioxidant effect compared to that of the palmitate. In an accelerated storage test using deodorized rapeseed oil, samples incubated with ascorbyl palmitate showed noticeable oxidation after 1 wk of storage, whereas samples incubated with ascorbyl oleate displayed negligible oxidation for 9 and 4 wk at 30 and 40°C, respectively.Paper no. J10512 in JAOCS 80, 795-799 (August 2003).Ascorbyl palmitate is a fat-soluble antioxidant commonly used in foods to prevent oxidation of sensitive fats and oils. Ascorbyl palmitate has a disadvantage, however, in that it has relatively low solubility in oils. The solubility can be improved by the addition of lecithin, although this causes the product to become hygroscopic. Another way to improve the solubility of an ascorbyl FA ester is to modify its structure to make it less crystalline. This can be done, for example, by introducing a double bond in the FA. Oleic acid is unsaturated, readily available, inexpensive, and approved for use in foods. This makes it an attractive candidate to replace the palmitic acid in an ascorbyl ester. The chemical synthesis of saturated ascorbyl FA esters is straightforward (1). A similar procedure for the synthesis of ascorbyl oleate has been described in the literature (2) but has proven hard to repeat. The difficulties are due to the double bond of oleic acid, which is too sensitive for the reaction conditions needed for the chemically catalyzed esterification. Enzymatic catalysis, however, can be performed at lower reaction temperatures and under milder conditions, enabling the enzymatic synthesis of ascorbyl oleate (Scheme 1). Because the reactants differ in polarity, the number of suitable solvents available is limited. We used t-amyl alcohol because it dissolves the reactants at high concentrations and does not deactivate the enzyme.In 1971, Arakawa et al.(3) reported on the first enzymatic synthesis of ascorbyl laurate in aqueous solution. In 1990, Enomoto et al. (4) filed a patent on the esterification in organic solvents, and esterfications in t-amyl alcohol were reported by Humeau et al. (5) in 1995. Since then, not only saturated FA have been used, but also various unsaturated FA (6-8) as well as of phenyl butyric acid (9) and methyl lactate (10). These syntheses have typically reached yields below 50% unles...

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“…83 The Schiffbase formation of acetaldehyde with lipase might present a problem. 84,85 In addition, vinyl esters are much more expensive than esters, which is no benefit to industrialization.…”

Section: Property Of Substratementioning

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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Study of Vitamin Ester Synthesis by Lipase-Catalyzed Transesterification in Organic Media

Cited by 43 publications

References 8 publications

Lipase-Catalyzed Transformations for the Synthesis of Butyl Lactate: A Comparison between Esterification and Transesterification

Lipase-Catalyzed Transformations for the Synthesis of Butyl Lactate: A Comparison between Esterification and Transesterification

Antioxidative properties and enzymatic synthesis of ascorbyl FA esters

Enzyme‐catalyzed regioselective synthesis of sucrose‐based esters

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