Scalable synthesis of highly pure 2‐monoolein by enzymatic ethanolysis

Wang, Xiaosan; Liang, Li; Yu, Zhenzhen; Rui, Lilian; Jin, Qingzhe; Wang, Xingguo

doi:10.1002/ejlt.201400004

Cited by 20 publications

(10 citation statements)

References 34 publications

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“…Moreover, ethanolysis reaction was carried out in pure ethanol without the use of an additional solvent as reaction medium. Whereas, other authors described the production of 2-MAGs by ethanolysis using acetone [31,32] or hexane [33] as reaction medium. The advantage of using pure ethanol, besides of being a green solvent allowed in food www.advancedsciencenews.com www.ejlst.com industry, lies in the fact that solvent is critical to acyl migration rate.…”

Section: Enzymatic Synthesis Of 2-mags From Camelina Oilmentioning

confidence: 99%

Strategies for Enzymatic Synthesis of Omega‐3 Structured Triacylglycerols from Camelina sativa Oil Enriched in EPA and DHA

Castejón

Señoráns

2019

Euro J Lipid Sci & Tech

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Enzymatic production of enriched eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA) structured triacylglycerols (STAGs) is done in a two‐step reaction from a new source of omega‐3 α‐linolenic acid (ALA), Camelina sativa oil. A fast‐pressurized liquid extraction method with ethyl acetate as green solvent is used to produce camelina oil with a 39.3% yield in less than 20 min. In a first stage, camelina oil with a 29.7% of ALA is used to enzymatically produce 2‐monoacylglycerols (2‐MAGs) with high ALA composition in position sn‐2 (49.8% of ALA) using Lipozyme TL IM at 25 °C. For omega‐3 incorporation into STAGs, several lipases are studied, with 2‐MAG and omega‐3 FAEEs at different ratios (1:5, 1:10, and 1:20 (w/w)), 10% (w/w) of biocatalyst at 35 °C. STAGs yields reached with EPA ethyl esters are notably higher than using DHA‐EE. Lipase from Candida antarctica B (CAL‐B) and Thermomyces lanuginosus (TLL) incorporate EPA into STAGs in the same degree, 95.1 and 95.5%, respectively. However, for enriched DHA STAGs, maximum reaction yield is reached with CAL‐B (81.0%). The transesterification method of 2‐MAGs from vegetable omega‐3 sources like camelina oil, with marine EPA and DHA FAEEs, opens new approaches for developing VLC‐PUFA fortified functional foods. Practical Applications: Results provided in this research not only demonstrate the efficiency of this enzymatic method for enriching camelina oil in EPA and DHA, but offer a very effective strategy for the development of omega‐3‐enriched products from other vegetable oil sources like chia or echium as ingredients for functional foods with recognized health claims for applications in nutraceutical and food industries. Camelina oil proved to be an excellent source to enzymatically produce 2‐MAGs enriched in omega‐3 ALA. Moreover, lipase screening with commercial biocatalysts establish the most appropriate strategy to reach maximum STAGs yields with direct application in industry. Tested lipases exhibit different degree of substrate specificity toward EPA and DHA, omega‐3 acids not present in natural seed oils. Thus, CAL‐B seems to be the most suitable lipase to produce high content EPA and DHA enriched STAGs from camelina oil as new food ingredients for nutraceutical applications. Enzymatic production of structured TAGs enriched in EPA and DHA is done in a two‐step reaction from a natural source of omega‐3 ALA, camelina oil, studying reaction kinetics and characterizing isolated products.

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Section: Enzymatic Synthesis Of 2-mags From Camelina Oilmentioning

confidence: 99%

Strategies for Enzymatic Synthesis of Omega‐3 Structured Triacylglycerols from Camelina sativa Oil Enriched in EPA and DHA

Castejón

Señoráns

2019

Euro J Lipid Sci & Tech

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“…The final product is purified via supercritical CO 2 (Soto et al., ). Ethanolysis can also be used as a methanol substitute (Wang et al., ). A method to produce monoacylglycerols via glycerolysis by using methyl esters of fatty acids, which are produced during manufacturing of biodiesel coming from linseed oil has also been reported (Schultz et al., ).…”

Section: Assessmentmentioning

confidence: 99%

Re‐evaluation of mono‐ and di‐glycerides of fatty acids (E 471) as food additives

Younes¹,

Aggett²,

Aguilar³

et al. 2017

EFS2

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The EFSA Panel on Food Additives and Nutrient Sources added to Food (ANS) provides a scientific opinion re-evaluating the safety of mono-and di-glycerides of fatty acids (E 471) when used as a food additive. The Panel considered that it is very likely that hydrolysis of mono-and di-glycerides of fatty acids by lipases in the gastrointestinal tract would occur, resulting in the release of glycerol and fatty acids. Glycerol (E 422) and fatty acids (E 570) have been re-evaluated and the Panel concluded that there was no safety concern regarding their use as food additives. Toxicological studies with mono-and di-glycerides rich in unsaturated fatty acids were considered for the re-evaluation of E 471. No evidence for adverse effects was reported in short-term, subchronic studies, chronic, reproductive and developmental toxicity studies. Neither carcinogenic potential nor a promotion effect in initiation/promotion was reported. The available studies did not raise any concern with regard to genotoxicity. The refined estimates were based on 31 out of 84 food categories in which E 471 is authorised. The Panel noted that the contribution of E 471 represented at the mean only 0.8-3.5% of the recommended daily fat intake. Based on the approach described in the conceptual framework for the risk assessment of certain food additives re-evaluated under Commission Regulation (EU) No 257/2010 and taking into account the considerations mentioned above, the Panel concluded that there was no need for a numerical acceptable daily intake (ADI) and that the food additive mono-and di-glycerides of fatty acids (E 471) was of no safety concern at the reported uses and use levels. The Panel recommended some modifications of the EU specifications for E 471.

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“…This monoglyceride is an important precursor for the synthesis of structured TAG. It is assumed that the 2MAG is generated by the alcoholysis of TAG with 1,3-specific lipases [28].…”

Section: Mole Fractions Of Monoacylglyceridesmentioning

confidence: 99%

An insight on acyl migration in solvent-free ethanolysis of model triglycerides using Novozym 435

Sánchez

Tonetto

Ferreira

2016

Journal of Biotechnology

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In this work, the ethanolysis of triglycerides catalyzed by immobilized lipase was studied, focusing on the secondary reaction of acyl migration. The catalytic tests were performed in a solvent-free reaction medium using Novozym 435 as biocatalyst. The selected experimental variables were biocatalyst loading (5-20mg), reaction time (30-90min), and chain length of the fatty acids in triglycerides with and without unsaturation (short (triacetin), medium (tricaprylin) and long (tripalmitin/triolein)). The formation of 2-monoglyceride by ethanolysis of triglycerides was favored by long reaction times and large biocatalyst loading with saturated short- to medium-chain triglycerides. In the case of long-chain triglycerides, the formation of this monoglyceride was widely limited by acyl migration. In turn, acyl migration increased the yield of ethyl esters and minimized the content of monoglycerides and diglycerides. Thus, the enzymatic synthesis of biodiesel was favored by long-chain triglycerides (which favor the acyl migration), long reaction times and large biocatalyst loading. The conversion of acylglycerides made from long-chain fatty acids with unsaturation was relatively low due to limitations in their access to the active site of the lipase.

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Scalable synthesis of highly pure 2‐monoolein by enzymatic ethanolysis

Cited by 20 publications

References 34 publications

Strategies for Enzymatic Synthesis of Omega‐3 Structured Triacylglycerols from Camelina sativa Oil Enriched in EPA and DHA

Strategies for Enzymatic Synthesis of Omega‐3 Structured Triacylglycerols from Camelina sativa Oil Enriched in EPA and DHA

Re‐evaluation of mono‐ and di‐glycerides of fatty acids (E 471) as food additives

An insight on acyl migration in solvent-free ethanolysis of model triglycerides using Novozym 435

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