Melting, Crystallization, and In Vitro Digestion Properties of Fats Containing Stearoyl-Rich Triacylglycerols

Fats containing the stearoyl-rich triacylglycerols (TAGs) of 1,2-distearoyl-3-oleoylglycerol (SSO) and 1,3-dioleoyl-2-stearoylglycerol (OSO) were synthesized via the lipase-catalyzed acidolysis of tristearin (SSS)-rich fat and oleic acids, followed by solvent fractionation. Their physicochemical properties and in vitro digestibilities were compared. The SSS-, SSO-, and OSO-rich fats comprised 81.6%, 52.9%, and 33.1% stearic acid, respectively, whereas oleic acid comprised 2.9%, 37.5%, and 56.2%, respectively. The SSS-, SSO-, and OSO-rich fats contained the TAGs of SaSaSa (100.00%), SaSaMo (86.98%), and MoSaMo (67.12%), respectively, and the major TAGs were SSS, SSO, and OSO, respectively. Melting and crystallization temperatures were higher and fat crystals were larger and densely packed in the descending order of SSS-, SSO and OSO-rich fats. Both in vitro multi-step digestion and pH-stat digestion were more rapid for OSO- than SSO-rich fat. Oleic acid was digested faster than stearic acid during the initial digestion, then the rate decreased, whereas that of stearic acid increased over prolonged digestion. Fats that were richer in stearoyl at the sn-1,3 position of TAG melted and crystallized at higher temperatures, had a densely packed microstructure of large fat crystals and were poorly digested. Stearic acid imparts the essential physical attributes of melting and crystallization in solid fats, and the low digestible stearoyl-rich fat would be a viable substitute for trans fatty acids in food lipid industry.

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Factors affecting lipase digestibility of emulsified lipids using an in vitro digestion model: Proposal for a standardised pH-stat method

Food Chemistry ◽

10.1016/j.foodchem.2010.11.027 ◽

2011 ◽

Vol 126 (2) ◽

pp. 498-505 ◽

Cited By ~ 187

Author(s):

Yan Li ◽

Min Hu ◽

David Julian McClements

Keyword(s):

In Vitro Digestion ◽

Factors Affecting ◽

Ph Stat ◽

Stat Method

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in-vitro Digestion of Water-in-oil Emulsions Stabilized with Fat Crystals

10.21748/am21.413 ◽

2021 ◽

Author(s):

Jonathan Andrade ◽

Dérick Rousseau ◽

Vivekkumar Patel

Keyword(s):

In Vitro Digestion ◽

Fat Crystals ◽

Oil Emulsions

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Edible lecithin, stearic acid, and whey protein bigels enhance survival of probiotics during in vitro digestion

Food Bioscience ◽

10.1016/j.fbio.2020.100813 ◽

2021 ◽

Vol 39 ◽

pp. 100813

Author(s):

Mark A. Bollom ◽

Stephanie Clark ◽

Nuria C. Acevedo

Keyword(s):

Stearic Acid ◽

Whey Protein ◽

In Vitro Digestion

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Stereospecific distribution of plamitic acid in the triacylglycerols of rat adipocytes. Effects of varying the composition of the substrate fatty acid in vitro

Biochemical Journal ◽

10.1042/bj1910637 ◽

1980 ◽

Vol 191 (2) ◽

pp. 637-643 ◽

Cited By ~ 2

Author(s):

William W. Christie ◽

Margaret L. Hunter

Keyword(s):

Fatty Acids ◽

Oleic Acid ◽

Fatty Acid ◽

Linoleic Acid ◽

Stearic Acid ◽

Palmitic Acid ◽

Myristic Acid ◽

Relative Proportion ◽

Rat Adipocytes

The effects of inclusion of different fatty acids in the medium on the rate of esterification of palmitic acid and its stereospecific distribution among the three positions of the triacyl-sn-glycerols by preparations of rat adipocytes in vitro have been determined. Myristic acid, stearic acid, oleic acid and linoleic acid were used as diluents and the concentration of the combined unesterified fatty acids in the medium was held constant; only the proportion of palmitic acid was varied. The amount of palmitic acid esterified was always linearly related to its relative concentration in the medium and was not significantly affected by the nature of the diluent fatty acid chosen. Constant relative proportions were recovered in triacylglycerols and in intermediates in each instance. The amount of palmitic acid esterified to each of the positions of the triacyl-sn-glycerols was linearly dependent on the relative proportion in the medium but the nature of the relationship was markedly influenced by which fatty acid was present. When stearic acid was present, simple relationships were found over the whole range tested. When either myristic acid, oleic acid or linoleic acid was present, abrupt changes in the manner of esterification of palmitic acid were observed in position sn-1 when the relative concentrations of palmitic acid and the diluent reached critical values, which differed with each fatty acid. In position sn-2 when oleic acid or linoleic acid was present, a similar change was observed, and in position sn-3 it was obtained with myristic acid as diluent. The results are discussed in terms of changes in the relative affinities of the acyltransferases for palmitic acid. Palmitic acid was esterified into various molecular species in proportions that indicated acylation with non-correlative specificity at higher relative concentrations but not at lower.

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Regiospecific Positioning of Palmitic Acid in Triacylglycerol Structure of Enzymatically Modified Lipids Affects Physicochemical and In Vitro Digestion Properties

Molecules ◽

10.3390/molecules26134015 ◽

2021 ◽

Vol 26 (13) ◽

pp. 4015

Author(s):

Hyeon-Jun Chang ◽

Jeung-Hee Lee

Keyword(s):

Fatty Acids ◽

Fatty Acid ◽

Palmitic Acid ◽

In Vitro Digestion ◽

Lower Content ◽

Melting Points ◽

Fat Crystals ◽

Triacylglycerol Structure ◽

Acetone Fractionation

Tripalmitin-(PPP, 81.2%), 1,3-dipalmitoyl-2-oleoylglycerol-(POP, 64.4%), 1,2-dipalmitoyl-3-oleoylglycerol-(PPO, 86.5%), and 1,3-dioleoyl-2-palmitoylglycerol-(OPO, 50.2%)-rich lipids with different regiospecific positions of palmitic acid (P) were synthesized via acetone fractionation and lipase-catalyzed acidolysis, and their physicochemical and hydrolytic characteristics were compared. Triacylglycerols (TAGs) with higher content of P, wherein P was at the sn-1 (or 3) position, had higher melting points, crystallization temperatures, and packing densities of fat crystals compared to those with a lower content of P, and with P at the sn-2 position. The in vitro digestion degree calculated as released fatty acid (FA) (%) at 30, 60, and 120 min was in the following order: OPO-rich > PPO-rich > POP-rich lipids. At 120 min, in vitro digestion of the OPO-rich lipid released 92.6% of fatty acids, resulting in the highest digestibility, while 89.7% and 87.2% of fatty acids were released from the OPO-rich and PPO-rich lipids, respectively. Over the digestion period, the TAG and monoacylglycerol (MAG) contents decreased, while the diacylglycerol (DAG) content initially increased and then decreased, and the 1,2-DAG content exceeded the 1,3-DAG content. Therefore, the content and stereospecific position of P attached to a specific TAG affected the physicochemical and in vitro digestion characteristics of the lipids.

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Investigations of in vitro bioaccessibility from interesterified stearic and oleic acid-rich blends

Food & Function ◽

10.1039/c5fo01272d ◽

2016 ◽

Vol 7 (4) ◽

pp. 1932-1940 ◽

Cited By ~ 9

Author(s):

S. H. Thilakarathna ◽

M. Rogers ◽

Y. Lan ◽

S. Huynh ◽

A. G. Marangoni ◽

...

Keyword(s):

Oleic Acid ◽

Stearic Acid ◽

Acid Absorption ◽

High Oleic ◽

Human Volunteers ◽

In Vitro Bioaccessibility

Interesterification was previously found to impact stearic acid absorption in a randomized cross-over study, when human volunteers consumed a 70 : 30 wt% high-oleic sunflower and canola stearin blend (NIE) compared to the same blend which had undergone either chemical (CIE) or enzymatic (EIE) interesterification.

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In vitro digestion of foods using pH-stat and the INFOGEST protocol: Impact of matrix structure on digestion kinetics of macronutrients, proteins and lipids

Food Research International ◽

10.1016/j.foodres.2015.12.002 ◽

2016 ◽

Vol 88 ◽

pp. 226-233 ◽

Cited By ~ 47

Author(s):

Damien J.L. Mat ◽

Steven Le Feunteun ◽

Camille Michon ◽

Isabelle Souchon

Keyword(s):

In Vitro Digestion ◽

Matrix Structure ◽

Ph Stat ◽

Digestion Kinetics ◽

Kinetics Of

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Hydrolytic Properties of Algae Oil and DAG-Rich Algae Oil Using pH-Stat and Multi-Step In Vitro Digestion Models

Journal of the Korean Society of Food Science and Nutrition ◽

10.3746/jkfn.2018.47.11.1118 ◽

2018 ◽

Vol 47 (11) ◽

pp. 1118-1127

Author(s):

Hyeon-Jun Chang ◽

Bo-Ram Na ◽

Jeung-Hee Lee

Keyword(s):

In Vitro Digestion ◽

Ph Stat ◽

Algae Oil

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Development of a Controlled Release of Salicylic Acid Loaded Stearic Acid-Oleic Acid Nanoparticles in Cream for Topical Delivery

The Scientific World JOURNAL ◽

10.1155/2014/205703 ◽

2014 ◽

Vol 2014 ◽

pp. 1-7 ◽

Cited By ~ 14

Author(s):

J. O. Woo ◽

M. Misran ◽

P. F. Lee ◽

L. P. Tan

Keyword(s):

Particle Size ◽

Salicylic Acid ◽

Oleic Acid ◽

Stearic Acid ◽

Particle Size Analysis ◽

Spherical Particles ◽

Solid Matrix ◽

Size Analysis ◽

Scanning Calorimetry

Lipid nanoparticles are colloidal carrier systems that have extensively been investigated for controlled drug delivery, cosmetic and pharmaceutical applications. In this work, a cost effective stearic acid-oleic acid nanoparticles (SONs) with high loading of salicylic acid, was prepared by melt emulsification method combined with ultrasonication technique. The physicochemical properties, thermal analysis and encapsulation efficiency of SONs were studied. TEM micrographs revealed that incorporation of oleic acid induces the formation of elongated spherical particles. This observation is in agreement with particle size analysis which also showed that the mean particle size of SONs varied with the amount of OA in the mixture but with no effect on their zeta potential values. Differential scanning calorimetry analysis showed that the SONs prepared in this method have lower crystallinity as compared to pure stearic acid. Different amount of oleic acid incorporated gave different degree of perturbation to the crystalline matrix of SONs and hence resulted in lower degrees of crystallinity, thereby improving their encapsulation efficiencies. The optimized SON was further incorporated in cream and itsin vitrorelease study showed a gradual release for 24 hours, denoting the incorporation of salicylic acid in solid matrix of SON and prolonging thein vitrorelease.

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