Synthesis of symmetrical structured triglycerides via a bottom-up process

Abstract The synthesis of symmetrical structured triglycerides (STG) through a bottom-up approach was previously shown to produce 1,3-dioleoyl-2-palmitoyl glycerol in significant quantities. This solvent-free lipase-catalyzed process, consisting of a low-temperature (40 °C) esterification step with glycerol dosing followed by a high-temperature (60 °C) esterification step, was further investigated in the production of symmetrical medium-and-long-chain triglycerides (MLCT). By replacing oleic acid with capric acid in the first step or the palmitic acid by either capric acid or lauric acid in the second step, the effects of free fatty chain length and sequence of fatty acid addition on STG production were established. These produced 1,3-dicaproyl-2-oleoyl glycerol, 1,3-dioleoyl-2-caproyl glycerol, and 1,3-dioleoyl-2-lauroyl glycerol at concentrations of 36.98 g, 36.77 g, and 37.08 g per 100 g of triglycerides respectively after 72 h at an overall FFA1:FFA2:Glycerol of 2:1:1 and 4 g Novozyme 435 per 100 g reactants, without the purification of intermediates and products. The sequence of fatty acid addition had the most significant effect as purer STG products can be obtained when the medium chain fatty acid is introduced in the first step. As the process was carried out without solvents, the STG produced are appropriate for functional food or nutraceutical applications.

Download Full-text

Temperature Dependence of the Critical Electron Dose for Fatty Acid Monolayers

Proceedings, annual meeting, Electron Microscopy Society of America ◽

10.1017/s0424820100053188 ◽

1982 ◽

Vol 40 ◽

pp. 78-79

Author(s):

Kenneth H. Downing ◽

Robert M. Glaeser

Keyword(s):

Electron Beam ◽

Fatty Acid ◽

Inelastic Scattering ◽

Temperature Dependence ◽

Structural Damage ◽

Direct Result ◽

Second Step ◽

Strong Temperature Dependence ◽

Electron Dose ◽

Covalent Bonds

The structural damage of molecules irradiated by electrons is generally considered to occur in two steps. The direct result of inelastic scattering events is the disruption of covalent bonds. Following changes in bond structure, movement of the constituent atoms produces permanent distortions of the molecules. Since at least the second step should show a strong temperature dependence, it was to be expected that cooling a specimen should extend its lifetime in the electron beam. This result has been found in a large number of experiments, but the degree to which cooling the specimen enhances its resistance to radiation damage has been found to vary widely with specimen types.

Download Full-text

Determination of fatty acid content in some edible insects of Mexico

Journal of Insects as Food and Feed ◽

10.3920/jiff2015.0078 ◽

2016 ◽

Vol 2 (1) ◽

pp. 37-42 ◽

Cited By ~ 6

Author(s):

J.M. Pino Moreno ◽

A. Ganguly

Keyword(s):

Oleic Acid ◽

Fatty Acid ◽

Acid Content ◽

Periplaneta Americana ◽

Fatty Acid Content ◽

Capric Acid ◽

Caproic Acid ◽

Insect Species ◽

Edible Insects

In the present paper we have determined the fatty acid content of some edible insects of Mexico. A comparative analysis of the insect species studied in this research showed that caproic acid was present in a minimal proportion which ranged between 0.01 for Periplaneta americana (nymphs) and 0.06 (g/100 g, dry basis) for Euschistus strenuus. The highest proportion of caprilic acid (0.09) was found in Tenebrio molitor (adults). Atta sp. had the highest amount of capric acid (0.26). Polistes sp. was found to be rich in lauric acid (0.77) and for myristic acid it had the highest content (5.64). Dactylopius sp. and E. strenuus were rich in palmitic acid (14.89). Euschistus taxcoensis had the highest quantity of palmitoleic acid (12.06). Llaveia axin exhibited the highest quantity of stearic acid (22.75). Polistes sp. was found to be rich in oleic acid (38.28). The highest quantity of linoleic acid was observed in T. molitor (larvae) (10.89), and in L. axin the highest content of linolenic acid (7.82) was obtained. A comparison between the species under the present investigation revealed that, in general, the insects are poor in caproic, caprilic, capric, lauric, myristic, palmitoleic and linolenic acids, because the quantities were either minimal or could not be detected at all. They had moderate quantities of stearic, palmitic and linoleic acids and had high quantities of oleic acid. Finally it was concluded that although a particular insect species is unable to fulfil the total fatty acid need for a human, if consumed in combination they could definitely be able to supply a good amount of this highly valued nutrient.

Download Full-text

Omega-3 fatty acid addition during pregnancy

Cochrane Database of Systematic Reviews ◽

10.1002/14651858.cd003402.pub3 ◽

2018 ◽

Cited By ~ 39

Author(s):

Philippa Middleton ◽

Judith C Gomersall ◽

Jacqueline F Gould ◽

Emily Shepherd ◽

Sjurdur F Olsen ◽

...

Keyword(s):

Fatty Acid ◽

Omega 3 ◽

Omega 3 Fatty Acid ◽

Acid Addition

Download Full-text

Can omega-3 fatty acid addition during pregnancy help improve maternal outcomes?

Cochrane Clinical Answers ◽

10.1002/cca.2491 ◽

2019 ◽

Author(s):

Carlos Fernando Grillo-Ardila

Keyword(s):

Fatty Acid ◽

Maternal Outcomes ◽

Omega 3 ◽

Omega 3 Fatty Acid ◽

Acid Addition

Download Full-text

Fatty acid is a potential agent for bone tissue induction: In vitro and in vivo approach

Experimental Biology and Medicine ◽

10.1177/1535370217731104 ◽

2017 ◽

Vol 242 (18) ◽

pp. 1765-1771 ◽

Cited By ~ 6

Author(s):

Guinea BC Cardoso ◽

Erivelto Chacon ◽

Priscila GL Chacon ◽

Pedro Bordeaux-Rego ◽

Adriana SS Duarte ◽

...

Keyword(s):

Stem Cells ◽

Oleic Acid ◽

Fatty Acid ◽

Bone Tissue ◽

In Vivo Studies ◽

Surrounding Tissue ◽

Bone Induction ◽

Acid Addition

Our hypothesis was to investigate the fatty acid potential as a bone induction factor. In vitro and in vivo studies were performed to evaluate this approach. Oleic acid was used in a 0.5 wt.% concentration. Polycaprolactone was used as the polymeric matrix by combining solvent-casting and particulate-leaching techniques, with a final porosity of 70 wt.%, investigated by SEM images. Contact angle measurements were produced to investigate the influence of oleic acid on polycaprolactone chains. Cell culture was performed using adipocyte-derived stem cells to evaluate biocompatibility and bioactivity properties. In addition, in vivo studies were performed to evaluate the induction potential of oleic acid addition. Adipocyte-derived stem cells were used to provide differentiation after 21 days of culture. Likewise, information were obtained with in vivo data and cellular invagination was observed on both scaffolds (polycaprolactone and polycaprolactone /oleic acid); interestingly, the scaffold with oleic acid addition demonstrated that cellular migrations are not related to the surrounding tissue, indicating bioactive potential. Our hypothesis is that fatty acid may be used as a potential induction factor for bone tissue engineering. The study’s findings indicate oleic acid as a possible agent for bone induction, according to data on cell differentiation, proliferation, and migration. Impact statement The biomaterial combined in this study on bone regeneration is innovative and shows promising results in the treatment of bone lesions. Polycaprolactone (PCL) and oleic acid have been studied separately. In this research, we combined biomaterials to assess the stimulus and the speed of bone healing.

Download Full-text

Mechanochemo-enzymatic Synthesis of Aromatic Aldehyde Oxime Esters

Natural Product Communications ◽

10.1177/1934578x1801300723 ◽

2018 ◽

Vol 13 (7) ◽

pp. 1934578X1801300

Author(s):

Margarita A. Arthur-Santiago ◽

Rosa María Oliart-Ros ◽

María G. Sánchez-Otero ◽

Gerardo Valerio-Alfaro

Keyword(s):

Aromatic Aldehyde ◽

Candida Rugosa ◽

Hydroxylamine Hydrochloride ◽

Aromatic Aldehydes ◽

Second Step ◽

Acyl Donor ◽

Porcine Pancreas ◽

H Nmr ◽

Novozyme 435 ◽

Porcine Pancreas Lipase

The synthesis of aromatic aldehyde oxime esters (considered fragrances, antifungal and antimicrobial compounds) was achieved by two reactions which combine the advantage of green chemistry and biocatalysis. In the first step, the mechanochemical oxime synthesis by means of grindstone milling of six solid aromatic aldehydes and hydroxylamine hydrochloride in the presence of FlorisilR, as the best support, yielded the aromatic aldehyde oximes 1–6 with high purity and good yields. In the second step the lipase catalyzed acetylation reaction at 40°C for three days of those oximes with vinyl and isopropenyl acetates as acyl donor substrates and ethyl acetate as the solvent, yielded the aromatic aldehyde oxime esters. With Candida antarctica lipase (Novozyme 435), the conversions of oximes 1–6 into their esters were ≥ 99% according to the 1H NMR results and it was the best biocatalyst compared with others such as Candida rugosa (CRL), porcine pancreas lipase and the recombinant lipase LipMatCCR11 from the thermophilic strain Geobacillus thermoleovorans CCR11 cloned and expressed in Escherichia coli BL21 (DE3), all of which showed lower yields.

Download Full-text

The Toxic Effects of Fatty Acids and Their Salts on the Balsam Woolly Aphid, Adelgespiceae (Ratz.)

Canadian Journal of Forest Research ◽

10.1139/x75-075 ◽

1975 ◽

Vol 5 (4) ◽

pp. 515-522 ◽

Cited By ~ 19

Author(s):

George S. Puritch

Keyword(s):

Fatty Acids ◽

Oleic Acid ◽

Fatty Acid ◽

Saturated Fatty Acid ◽

Capric Acid ◽

The Other ◽

Toxic Effects ◽

Life Stages ◽

Woolly Aphid ◽

Oleic And Linoleic Acids

Fatty acids and their potassium soaps were screened for their toxicity to different life stages and eggs of the balsam woolly aphid (Adelgespiceae (Ratz.)). The most effective fatty acids for causing aphid mortality were in two major groups, one centering around capric acid (C10) within the low-chain saturated fatty acid series and the other around oleic acid (C18:1), within the unsaturated 18-carbon fatty acids. The potassium soaps were better aphicides than the corresponding acids; the soaps of caprylic, capric, oleic, and linoleic acids were the most effective. Eggs were less sensitive to the soaps than later stages of the aphid, and there was a large variation in their response to the soap treatments. The possibility of using fatty acids and soaps as a control for the balsam woolly aphid is discussed.

Download Full-text