Physicochemical Properties of Diacylglycerol

Novel functional groups can be introduced into vegetable oils using enzymes, resulting in value-added products. The transesterification kinetics of ethyl ferulate with MAG, DAG, and TAG were examined. Transesterification was catalyzed by immobilized Candida antarctica lipase B in solventless batch and packed-bed reactors. Initial reaction rates with TAG were slightly sensitive to water activity, whereas rates with MAG and DAG were water activity independent. Transesterification was also three-to sixfold faster with MAG and DAG. These observations indicate that the reaction is rate limited by the acyl acceptor, and that oils with free hydroxyl groups are preferred acyl acceptors in comparison with TAG, which must undergo partial hydrolysis before becoming reactive.

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“…Based on FA composition and acylglycerol distribution (17), average M.W. of 751 and 660 were estimated for PD-SBO and EDO, respectively.…”

Section: Resultsmentioning

confidence: 99%

Enzymatic glycerolysis and transesterification of vegetable oil for enhanced production of feruloylated glycerols

Laszlo

Compton

2006

J Americ Oil Chem Soc

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“…Acyl migration is an isomerization reaction that takes place spontaneously in MAG and DAG. The thermodynamically stable percentage of 1,3-DAG in a DAG isomer mixture is known to be between 60 and 70% [6,7]. In the last step of the proposed process we aim to increase the percentage of 1,3-DAG in the AG mixture produced by ethanolysis, up to the stable thermodynamic ratio.…”

Section: Maximizing the Proportion Of 13-dag By Acyl Migrationmentioning

confidence: 99%

“…Two DAG isomers exist: 1,2-DAG (and its equivalent 2,3-DAG) and 1,3-DAG, in a thermodynamically stable ratio between 4:6 and 3:7 [6,7]. Due to its digestion pathway, the 1,3-DAG isomer is believed to be the main responsible of the interesting nutritional properties of DAG [5].…”

Section: Introductionmentioning

confidence: 98%

A process for the production of a diacylglycerol‐based milk fat analogue

Lubary

Hofland

Horst

2010

Euro J Lipid Sci & Tech

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We propose a novel process for the production of a DAG-rich acylglycerol mixture derived from milk fat. This product has potentially interesting nutritional properties, derived from both its high content of DAG and of short-chain fatty acids (FAs). The proposed process consists of three steps: lipase-catalysed partial ethanolysis of milk fat, extraction of the by-product fatty acid ethyl esters (FAEEs) using supercritical carbon dioxide (SC-CO 2 ) and isomerization of DAG to increase the proportion of 1,3-DAG. The experimental investigation of the process steps was done using milk fat and trilaurin. Several lipases were tested for maximizing the percentage of DAG in the acylglycerol mixture produced by ethanolysis. The selectivity of the chosen lipase was such that the produced AG mixture was enriched in short-chain FAs in relation to the original milk fat. FAEEs were completely extracted from the ethanolysis mixture by SC-CO 2 . In the final process step, we explored the reaction conditions for facilitating acyl migration in the DAG mixture, so that the equilibrium proportion of 1,3-DAG (64%) was attained. Our results set the basis for the development of a simple process for the production of a DAG-rich milk fat analogue.

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“…The ratio of 1,3-DAG and 1,2-DAG was 7 : 3 due to acyl migration during storage and heating during the production process (2). Thus, the final composition of the test DAG oil was 10% TAG, 27% 1,2-DAG, and 63% 1,3-DAG.…”

Section: Discussionmentioning

confidence: 92%

“…DAG is used as a food additive in small amounts, but the 1,3-specific lipase-catalyzed reverse reaction currently allows for large-scale production of DAG, which is commercially available in the United States and Japan as cooking oil and in fat products. DAG occurs in two isoforms, 1,2 (or 2,3)-diacyl-sn -glycerol (1,2-DAG) and 1,3-diacyl-sn -glycerol (1,3-DAG) ( 2 ). In most natural edible oils and manufactured DAG oil, the 1,3-and 1,2-isoforms are present in a 7 : 3 ratio (w/w) ( 3 ).…”

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confidence: 99%

Size-Based Distributions of Postprandial Lipoproteins in Lymph and Serum after Oral Administration of Triacylglycerol and Diacylglycerol Oils in Rats

Saito

Nakagiri

Watanabe

et al. 2008

J Nutr Sci Vitaminol

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Summary Several studies in humans and rodents suggest that postprandial serum triglyceride (TG) levels are decreased by a single oral administration of diacylglycerol (DAG) oil compared with administration of control triacylglycerol (TAG) oil. To gain further insight into the mechanisms underlying the metabolic properties of DAG in a postprandial state, we analyzed the size-based distributions of postprandial lipoproteins in the lymph and serum using gel filtration-based high-performance liquid chromatography. In thoracic duct lymph pooled for 3 h after oral administration of TAG or DAG, the size-based distributions of postprandial lymphatic lipoprotein-TG and -cholesterol levels did not differ significantly, suggesting that DAG did not affect the size of lipoprotein particles secreted from the small intestine. Serum lipoprotein-TG (60%) and -cholesterol levels (90%), however, were significantly different among fractions with a diameter of greater than 80 nm 1 to 2 h after the administration of DAG compared to TAG. In addition, there was a considerable, but nonsignificant, reduction in lipoprotein-TG levels (~ 40%) in fractions with a diameter of 80 to 30 nm, suggesting that DAG-derived chylomicrons as well as DAG-derived chylomicron remnants were catabolized rapidly. In conclusion, dietary DAG reduced the amount of large-size lipoproteins in the serum, but did not affect the size distribution of lipoproteins produced in the small intestine. Thus, compared with TAG, dietary DAG may reduce the postprandial serum total TG levels.

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Physicochemical Properties of Diacylglycerol

Cited by 15 publications

References 18 publications

Enzymatic glycerolysis and transesterification of vegetable oil for enhanced production of feruloylated glycerols

Enzymatic glycerolysis and transesterification of vegetable oil for enhanced production of feruloylated glycerols

A process for the production of a diacylglycerol‐based milk fat analogue

Size-Based Distributions of Postprandial Lipoproteins in Lymph and Serum after Oral Administration of Triacylglycerol and Diacylglycerol Oils in Rats

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