- Enzymatic transesterification of palm olein with nonspecific and 1,3-specific lipases
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The enzymatic transesterification of palm olein was conducted in a low-moisture medium with nonspecific and 1,3-specific lipases from microbial sources. The enzymes were first immobilized on Celite, lyophilized for 4 h and then added to a reaction medium that consisted of 10% (wt/vol) palm olein in water-saturated hexane. The catalytic performance of the enzymes was evaluated by determining the changes in triglyceride (TC) composition and concentrations by reverse-phase high-performance liquid chromatography (HPLC) and the formation of free fatty acids by titration. Studies with lipase from Candida rugosa showed that the degree of hydrolysis was reduced by drying the immobilized preparation and that the best drying time was 4 h. In all cases, the transesterification process resulted in the formation of PPP, a TG initially undetected in the oil, and increases in the concentrations of OOO (1.3-2.1 -fold), OOL (1.7-4.5-fold), and OLL (1.7-4.3-fold), where P, O, and L are palmitic, oleic, and linoleic acids, respectively. SOS (where S is stearic acid), another TC not detected in the oil, was synthesized by Rhizomucor miehei and Pseudomonas lipases, with the latter producing more of this TG. There was a corresponding decrease in the concentrations of POP, PLP, POO, and POL. PPP concentration ranged from 1.9% (w/w) for Mucor javanicus lipase to 6.2% (w/w) for Pseudomonas lipase after 24 h. The greatest degree and fastest rate of change were caused by Pseudomonas lipase, followed by the enzymes from R. miehei and Aspergillus niger. The effects of transesterification and hydrolysis of palm olein by the various lipases resulted in changes in the overall degree of saturation of the triglyceride components. There seems to be no clear correlation between the enzyme positional specificity and the products formed. Possible mechanisms for the formation of PPP, OOL, OLL, OOO, and SOS are discussed. Copyright
- Ghazali,Hamidah,Che Man
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Read Online
- CONCEPT FOR THE PRODUCTION OF FOOD WITH REDUCED ENVIRONMENTAL IMPACT
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Edible organic compounds which can serve as food or feed, or as components of food or feed, are synthesized from oxidized carbon and water, through the input of energy, and using well-known and validated synthesis pathways, leading to free fatty acids and optionally esterified to triglycerides. The source of carbon is preferably C02 from the atmosphere, or more preferably point sources of C02 from industry and/or energy production.
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Paragraph 099-0100
(2020/03/05)
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- Monomyristin and monopalmitin derivatives: Synthesis and evaluation as potential antibacterial and antifungal agents
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In the present work, monoacylglycerol derivatives, i.e., 1-monomyristin, 2-monomyristin, and 2-monopalmitin were successfully prepared from commercially available myristic acid and palmitic acid. The 1-monomyristin compound was prepared through a transesterification reaction between ethyl myristate and 1,2-O-isopropylidene glycerol, which was obtained from the protection of glycerol with acetone, then followed by deprotection using Amberlyst-15. On the other hand, 2-monoacylglycerol derivatives were prepared through enzymatic hydrolysis of triglycerides in the presence of Thermomyces lanuginosa lipase enzymes. The synthesized products were analyzed using fourier transform infrared (FTIR) spectrophotometer, gas or liquid chromatography-mass spectrometer (GC-MS or LC-MS), and proton and carbon nuclear magnetic resonance (1H- and13C-NMR) spectrometers. It was found that monomyristin showed high antibacterial and antifungal activities, while 2-monopalmitin did not show any activity at all. The 1-monomyristin compound showed higher antibacterial activity against Staphylococcus aureus and Aggregatibacter actinomycetemcomitans and also higher antifungal activity against Candida albicans compared to the positive control. Meanwhile, 2-monomyristin showed high antibacterial activity against Escherichia coli. The effect of the acyl position and carbon chains towards antibacterial and antifungal activities was discussed.
- Jumina,Nurmala, Asma,Fitria, Anggit,Pranowo, Deni,Sholikhah, Eti Nurwening,Kurniawan, Yehezkiel Steven,Kuswandi, Bambang
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- PALM OIL ENRICHED IN UNSATURATED FATTY ACIDS
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A process for producing a food oil containing at least 50% monounsaturated fatty acids from palm oil is disclosed. Fatty acids are released from palm oil glycerides, such as by fat-splitting. The free fatty acids (FFA) are separated to obtain a fraction enriched in unsaturated palm fatty acid. This fraction is subject to a condensation reaction with glycerol to form an oil comprising mainly triglycerides (triacylglycerols). The condensation reaction is catalyzed by an enzyme.
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Paragraph 0093; 0094
(2013/06/06)
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- MALLEABLE, BIODEGRADABLE HEMOSTATIC AGENT
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A malleable, biodegradable hemostatic agent is provided that can be used for mechanical sealing of bleeding bone tissue, as well as a method for forming a malleable, biodegradable hemostatic agent of this type, and a medical implant having a coating that includes a malleable, biodegradable hemostatic agent of this type. The malleable, biodegradable hemostatic agent contains (a) at least one saturated glycerol-1,2,3-tri-fatty acid ester having a melting temperature above 37° C., (b) at least one filling agent present in particulate form, at least in part, and having a melting temperature above 37° C., and (c) at least one compound having a melting temperature not above 37° C. and a solubility at a temperature of 25° C. of less than 50 grams per liter of water.
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- 13C NMR quantification of mono and diacylglycerols obtained through the solvent-free lipase-catalyzed esterification of saturated fatty acids
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In the present investigation, we studied the enzymatic synthesis of monoacylglycerols (MAG) and diacylglycerols (DAG) via the esterification of saturated fatty acids (stearic, palmitic and an industrial residue containing 87% palmitic acid) and glycerol in a solvent-free system. Three immobilized lipases (Lipozyme RM IM, Lipozyme TL IM and Novozym 435) and different reaction conditions were evaluated. Under the optimal reaction conditions, esterifications catalyzed by Lipozyme RM IM resulted in a mixture of MAG and DAG at high conversion rates for all of the substrates. In addition, except for the reaction of industrial residue at atmospheric pressure, all of these products met the World Health Organization and European Union directives for acylglycerol mixtures for use in food applications. The products were quantified by 13C NMR, with the aid of an external reference signal which was generated from a sealed coaxial tube filled with acetonitrile-d3. After calibrating the area of this signal using the classical external reference method, the same coaxial tube was used repeatedly to quantify the reaction products. Copyright
- Fernandes, Jane Luiza Nogueira,De Souza, Rodrigo Octavio Mendonca Alves,De Vasconcellos Azeredo, Rodrigo Bagueira
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experimental part
p. 424 - 428
(2012/08/14)
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- Synthesis and physical properties of symmetrical and non-symmetrical triacylglycerols containing two palmitic fatty acids
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A series of symmetrical (ABA) and non-symmetrical (AAB) triacylglycerol (TAG) isomers containing "A," palmitic (P; 16:0) acid, and "B," either oleic (O; 9c-18:1), elaidic (E; 9t-18:1), linoleic (L; 9c,12c-18:2) or linolenic (Ln; 9c,12c,15c-18:3) fatty acids were synthesized by esterification of the thermodynamically more-stable 1,3-di- or 1(3)-monoacylglycerols [1,3-DAG or 1(3)-MAG], respectively. 1,3- dipalmitoylglycerol (1,3P-DAG) was esterified with O, L or Ln acid to prepare the symmetrical TAG isomers POP, PLP and PLnP, while the O- E-, L- and Ln-1(3)MAG precursors, synthesized or obtained commercially, were esterified with P acid to prepare the non-symmetrical TAG isomers OPP, EPP, LPP and LnPP, respectively. The drop point(s), solid fat content and melting point values of the synthesized TAG were determined. The 1,3-dipalmitoylglycerol (1,3P-DAG) and 1(3)P-MAG precursors were prepared, in multi-gram quantities, by partial glycerolysis (glycerol/p-toluenesulfonic acid) of tripalmitin. After fractionation by silica gel chromatography, the 1(3)P-MAG and 1,3P-DAG isomers (ca. 80% of total MAG or DAG) were purified (>98%) by crystallization from acetone [silver ion-HPLC was utilized to determine the structural purities of the DAG (or MAG) precursors, and the synthesized TAG]. Esterification of the appropriate, thermodynamically more-stable MAG or DAG precursors was found to be a very versatile method for synthesis (in 80-90% yields) of multi-gram (3-5 g) quantities of symmetrical and non-symmetrical TAG isomers, in chemical and structural purities of >96 and 97-99%, respectively.
- Adlof,List
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- Synthesis of the structured lipid 1,3-dioleoyl-2-palmitoylglycerol from palm oil
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Human milk fat contains 20-25% palmitic acid (16:0) and 30-35% oleic acid (18:1). More than 60% of the palmitic acid occurs at the sn-2 position of the glycerol backbone. Palm oil is a rich source of both palmitic and oleic acids. The structured lipid 1,3-dioleoyl-2-palmitoylglycerol (OPO) is an important ingredient in infant formula. OPO was synthesized from palm oil by a three-step method. In the first step, low-temperature fractionation was applied to palm oil FA, yielding a palmitic acid-rich fraction (87.8%) and an oleic acid-rich fraction (96%). The palmitic acid content was further increased to 98.3% by transforming palmitic acid into ethyl palmitate. In the second step, esterificalion of ethyl palmitate and glycerol catalyzed by lipase Novozym 435 under vacuum (40 mm Hg) was employed for the synthesis of tripalmitin. Finally, OPO was obtained by the reaction of tripalmitin with oleic acid catalyzed by Lipase IM 60. In this final step, the TAG content in the product acylglycerol mixture was 97%, and 66.1 % oleic acid was incorporated into TAG. Analysis of the FA composition at the sn-2 position of TAG showed 90.7 mol% of palmitic acid and 9.3 mol% of oleic acid. OPO content in the product TAG was ca. 74 mol%. Thus, an efficient method was developed for the synthesis of OPO from palm oil.
- Chen, Ming-Lung,Vali, Shaik Ramjan,Lin, Jih-Yao,Ju, Yi-Hsu
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p. 525 - 532
(2007/10/03)
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- Therapeutic compound-fatty acid conjugates
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A methotrexate conjugated to 1-3 acyl groups derived from fatty acids. In particular the invention relates to altering the pharmacokinetic profile and mode of delivery of methotrexate by conjugating it to 1.2 or 3 acyl derivatives of fatty acids.
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- 1H-Nuclear magnetic resonance spectroscopic studies of saturated, acetylenic and ethylenic triacylglycerols
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The 1H-NMR spectroscopic properties of 15 synthetic homologous saturated triacylglycerols of type AAA and 16 mixed saturated triacylglycerols of type ABA and AAB have been studied. Triacylglycerols containing short-chain fatty acids (2:0-6:0) are readily identified. Triacylglycerols containing medium- and long-chain fatty acid components are not differentiated. From the analysis of 19 acetylenic triacylglycerols of type AAA, ABA and AAB (containing positional isomers of acetylenic fatty acids), it is only possible to characterize triacylglycerols with acyl groups containing the acetylenic bond at the Δ2-Δ5 position. 1H-NMR analysis could not confirm the positions (α- or β-acyl) of the acetylenic acids in mixed triacylglycerols. In the study of 22 ethylenic triacylglycerols of type AAA containing positional isomers of (Z)- or (E)-ethylenic acids, molecules containing an ethylenic bond in the Δ2 position of the acyl chains were readily characterized, as the ethylenic protons in the α- and β-acyl chains were fully resolved. Triacylglycerols containing an unsaturated center at the position were characterized by the shifts of the 2-H protons. The spectra of the remaining triacylglycerol molecules were very similar and the position of the ethylenic system could not be determined by this technique.
- Lie Ken Jie, Marcel S.F.,Lam
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p. 155 - 171
(2007/10/03)
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- Fat Hydrolysis and Esterification by a Lipase from Humicola lanuginosa
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The hydrolysis and esterification by a thermostable lipase from Humicola lanuginosa No. 3 were investigated.Both reactions occurred readily at temperatures between 45-50 deg C.Esterification by the enzyme with glycerol was observed to be specific towards fatty acids with carbon numbers of C12-C18.Lauric acid esters with different alcohols such as primary alcohols, terpene alcohols, etc., were also synthesized readily.Esterification by the enzyme was adversely affected by the water content (optimum, ca. 7percent), however, the hydrolysis rate increased rapidly with increasing water content (optimum, ca. 60percent).The enzyme showed increased activity in organic solvent-aqueous reaction systems.Nevertheless, hydrolysis in complete organic phase reactions was found not to be feasible.Hydrolysis at a higher temperature (50 or 55 deg C) in a solvent free phase was almost the same as that in organic solvent-aqueous phase reactions.The components of glycerides varied considerably during hydrolysis, whereby esterification resulted in a higher quantity of mono- and diglycerides (about 40percent), compared to in the case of hydrolysis, for which the value was about 10-20percent.
- Omar, Ibrahim Che,Nishio, Naomichi,Nagai, Shiro
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p. 2153 - 2160
(2007/10/02)
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- A CONVENIENT METHOD OF ESTERIFICATION OF FATTY ACIDS. PREPARATION OF ALKYL ESTERS, STEROL ESTERS, WAX ESTERS AND TRIACYLGLYCEROLS
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A quick and mild, one-pot method of esterification of fatty acids with pripary, secondary and tertiary alcohols as well as with fatty alcohols, sterols and glycerol is proposed via the acyl bromides formed in situ.
- Saroja, M.,Kaimal, T. N. B.
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p. 1423 - 1430
(2007/10/02)
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- Topical corticosteroid formulations
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This present invention relates to a solution for topical or local application comprising at least one corticosteroid; from about 1% to 4% by weight of solubilization agents consisting essentially of a combination of at least one glyceryl ester of a fatty acid of 6 to 22 carbon atoms and a betaine surfactant, from about 10% to 50% by weight of composition of an alkanol cosolvent, and from about 20% to 50% water.
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- Coal tar gel composition
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Compositions effective for topically treating skin conditions, especially psoriasis and eczema which contains as an essential ingredient coal tar in a gel base.
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- Speckle particle for dentifrice
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Functional speckle particle suitable for use in dentifrice containing allantoin, aluminum dihydroxy allantoinate (ALDA) or aluminum chlorohydroxyallantoinate (ALCA). The speckle is effective in promoting healing of inflamed and bleeding gums or periodontal tissue.
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