- Synthesis of 2-Modified 1,3-Diacylglycerols
-
1,3-Diacylglycerols modified in 2-position were synthesized by combining enzymatic and chemical methods.The syntheses started from the regioisomerically pure 1,3-dilauroylglycerol or 1,3-dimyristoylglycerol obtained from glycerol and vinyl esters of carboxylic acids by means of lipase from Mucor mihei.The 2-hydroxyl group in the glycerol derivatives was subsequently substituted by phosphate as well as its disodium salt, by sulfate, phosphocholine, the benzyloxy, the succinimidyl or the amino group.
- Haftendorn, Regine,Ulbrich-Hofmann, Renate
-
-
Read Online
- Enzymatic esterification of lauric acid to give monolaurin in a microreactor
-
Monolaurin is a naturally occurring compound widely utilized in food and cosmetics. In this paper, we present a new method for the synthesis of monolaurin by esterification between lauric acid and glycerol catalyzed by Novozym 435 using a microreactor. The conversion of lauric acid is 87.04% in 20 min, compared with 70.54% via the batch approach in 5 h. Using an optimized solvent system consisting of t-BuOH/tert-amyl alcohol (1:1, v/v), the selectivity using the microreactor method is enhanced to 90.63% and the space–time yield of the process is 380.91 g/h/L. This newly devised method has the potential for application to other multiphase and enzymatic reactions.
- Li, Xin,Miao, Shanshan
-
p. 660 - 667
(2021/03/03)
-
- METHOD FOR PREPARING MONOGLYCERIDES
-
The present application relates to a method for preparing monoglycerides, a method for recovering glycerin and catalysts after the process for preparing monoglycerides, and a process for preparing cyclic monoglycerides.(AA) Fatty acid glycerin catalyst(BB) Esterification(CC) Reuse(DD) Settling and separation(EE) Glycerin and most of catalyst(F1,F2) Glyceride layer(GG) Glycerin(HH) Washing and separation(II) Glycerin and traces of catalyst(JJ) Glyceride layer(KK) Molecular distillation(LL) Glycerin and unreacted fatty acid(MM) Di- and tri-glycerideCOPYRIGHT KIPO 2020
- -
-
Paragraph 0076-0078
(2020/08/18)
-
- COMPOSITIONS AND METHODS FOR THE TREATMENT OF NEUROLOGICAL DISEASES
-
The invention relates to the compounds or its pharmaceutical acceptable polymorphs, solvates, enantiomers, stereoisomers and hydrates thereof. The pharmaceutical compositions comprising an effective amount of compounds of formula I, formula II and formula III and the methods for the treatment of neurological diseases may be formulated for oral, buccal, rectal, topical, transdermal, transmucosal, lozenge, spray, intravenous, oral solution, nasal spray, oral solution, suspension, oral spray, buccal mucosal layer tablet, parenteral administration, syrup, or injection. Such compositions may be used to treatment of neurological diseases.
- -
-
Page/Page column 49
(2019/10/19)
-
- COMPOSITIONS AND METHODS FOR THE TREATMENT OF FUNGAL INFECTIONS
-
The invention relates to the compounds or its pharmaceutical acceptable polymorphs, solvates, enantiomers, stereoisomers and hydrates thereof. The pharmaceutical compositions comprising an effective amount of compounds of formula I, formula II, formula III, formula IV, formula V, formula VI, formula VII, formula VIII, formula IX or Formula X and, the methods for the treatment of fungal infections may be formulated for oral, buccal, rectal, topical, transdermal, transmucosal, lozenge, spray, intravenous, oral solution, buccal mucosal layer tablet, parenteral administration, syrup, or injection. Such compositions may be used to treatment of fungal infections.
- -
-
Paragraph 00105
(2018/06/12)
-
- Towards engineering of self-assembled nanostructures using non-ionic dendritic amphiphiles
-
Engineering nanostructures of defined size and morphology is a great challenge in the field of self-assembly. Herein we report on the formation of supramolecular nanostructures of defined morphologies with subtle structural changes for a new series of dendritic amphiphiles. Subsequently, we studied their application as nanocarriers for guest molecules.
- Thota, Bala N. S.,Berlepsch, Hans V.,B?ttcher, Christoph,Haag, Rainer
-
supporting information
p. 8648 - 8651
(2015/05/20)
-
- Highly efficient solvent-free synthesis of 1,3-diacylglycerols by lipase immobilised on nano-sized magnetite particles
-
Recently, 1,3-DAGs (1,3-diacylglycerols) have attracted considerable attention as healthy components of food, oil and pharmaceutical intermediates. Generally, 1,3-DAG is prepared by lipase-mediated catalysis in a solvent free system. However, the system's high reaction temperature (required to reach the reactants' melting point), high substrate concentration and high viscosity severely reduce the lipase's activity, selectivity and recycling efficiency. In this report, MjL (Mucor javanicus lipase) was found to have the best performance in the solvent-free synthesis of 1,3-DAGs of several common commercial lipases. By covalent binding to amino-group-activated NSM (nano-sized magnetite) particles and cross-linking to form an enzyme aggregate coat, MjL's specific activity increased 10-fold, and was able to be reused for 10 cycles with 90% residual activity at 55 °C. 1,3-DAGs of lauric, myristic, palmitic, stearic, oleic and linoleic acid were prepared using the resulting immobilised enzyme, all with yields greater than 90%, and the reaction time was also greatly reduced.
- Meng, Xiao,Xu, Gang,Zhou, Qin-Li,Wu, Jian-Ping,Yang, Li-Rong
-
p. 319 - 324
(2013/10/08)
-
- Synthesis and tandem mass spectrometry of chlorinated triacylglycerols
-
The incorporation of 9,10-dichlorooctadecanoyl groups using enzyme-catalyzed acylation and protecting group strategies yielded specific regioisomers of di- and tetrachlorinated triacylglycerols. Hexachloroand hexabromotriacylglycerols were synthesized by addition of chlorine or bromine to tri-(cis-9-octadecenoyl)glycerol. Upon electrospray ionization and tandem mass spectrometry, the sodium adductions of all compounds containing a 9,10-dichlorooctadecanoyl group readily lost two molecules of HCl when subjected to collision-induced dissociation. A mechanism describing sequential HCl losses and the formation of a conjugated diene is proposed for the loss of both vicinal chlorine atoms from an alkyl chain. This characteristic fragmentation behavior and the availability of characterized standards will facilitate the development of quantitative analytical methods for the determination of chlorinated triacylglycerols in lipid mixtures isolated from marine and other biological sources.
- Lefsay, Abir M.,Guy, Robert D.,Chatt, Amares,White, Robert L.
-
-
- Use of glycerol carbonate in an efficient, one-pot and solvent free synthesis of 1,3-sn-diglycerides
-
An efficient solvent-free synthesis of a variety of highly pure 1,3-sn-diglycerides (1,3-sn-diacylglycerols) in a two-step one pot process is described. Heating glycerol carbonate (4-hydroxymethyl-1,3-dioxolan-2-one) with fatty acid anhydrides 2a-d affords 1:1 mixtures of glycerol carbonate fatty esters 3a-3d and the corresponding fatty acids. Further heating the reaction mixtures in the presence of catalytic amounts of 1,4-diazabicyclo[2.2.2]octane (DABCO) at 195-200 °C yields highly pure 1,3-sn-diglycerides 4a-4d.
- Kargar, Mojgan,Hekmatshoar, Rahim,Ghandi, Mehdi,Mostashari, Abdoljalil
-
p. 259 - 264
(2013/07/27)
-
- 1-O-Alkyl (di)glycerol ethers synthesis from methyl esters and triglycerides by two pathways: Catalytic reductive alkylation and transesterification/reduction
-
From available and bio-sourced methyl esters, monoglycerides or oleic sunflower refined oil, the corresponding 1-O-alkyl (di)glycerol ethers were obtained in both high yields and selectivity by two different pathways. With methyl esters, a reductive alkylation with (di)glycerol was realized under 50 bar hydrogen pressure in the presence of 1 mol% of Pd/C and an acid co-catalyst. A second two step procedure was evaluated from methyl esters or triolein and consisted of a first transesterification to the corresponding monoglyceride with a BaO/Al2O3 catalyst, then its reduction to the desired glycerol monoether with a recyclable heterogeneous catalytic system Pd/C and Amberlyst 35 under H2 pressure. In addition, a mechanism for the reaction was also proposed.
- Sutter, Marc,Dayoub, Wissam,Metay, Estelle,Raoul, Yann,Lemaire, Marc
-
supporting information
p. 786 - 797
(2013/04/24)
-
- Enzymatic synthesis of monoglycerides by esterification reaction using Penicillium camembertii lipase immobilized on epoxy SiO2-PVA composite
-
Glycerol-fatty acid esterification has been conducted with lipase from Penicillium camembertii lipase immobilized on epoxy SiO2-PVA in solvent-free media, with the major product being 1-monoglyceride, a useful food emulsifier. For a given set of initial conditions, the influence of reaction was measured in terms of product formation and selectivity using different fatty acids as acyl donors. Results were found to be relatively dependent of the chain length of the fatty acids, showing high specificity for both myristic and palmytic acids attaining final mixture that fulfills the requirements established by the World Health Organization to be used as food emulsifiers.
- Freitas, Larissa,Paula, Ariela V.,dos Santos, Julio C.,Zanin, Gisella M.,de Castro, Heizir F.
-
experimental part
p. 87 - 90
(2010/10/19)
-
- Large-scale synthesis of both symmetrical and unsymmetrical triacylglycerols containing docosahexaenoic acid
-
A large-scale (~100 g) synthesis of symmetrical and unsymmetrical triacylglycerols containg docosahexaenoic acid (D) and two of either lauric (L), palmitic (P) or stearic acid (S) is described. Key improvements in purification of synthetic intermediates, in addition to a more efficient acetonide cleavage reaction affords the six TAGs (LaDLa, LaLaD, PDP, PPD, SDS, SSD) in yields of 80-90% and in regioisomeric purities greater than or equal to 90%.
- Andrews, Philip C.,Fraser, Benjamin H.,Junk, Peter C.,Massi, Massimiliano,Perlmutter, Patrick,Thienthong, Neeranat,Wijesundera, Chakra
-
p. 9197 - 9202
(2008/12/22)
-
- High purity palm monoglycerides
-
The present invention relates to a process for producing high purity monoglycerides from edible oils/fats and fatty acids through glycerolysis, in particular but not exclusively to the production of monoglycerides from palm oil and palm oil products. This is achieved by providing a process for the production of monoglycerides of fatty acids or fats and oils, comprising the steps of reacting fatty acids or fats and oils with excess glycerol in the presence of an acidic or alkaline catalyst; substantially separating the crude reaction product from the other reaction components; removing unwanted reaction components from the crude reaction product by washing; drying the reaction product.
- -
-
Page/Page column 5
(2008/06/13)
-
- HYDROLASES, NUCLEIC ACIDS ENCODING THEM AND MEHODS FOR MAKING AND USING THEM
-
The invention provides hydrolases, polynucleotides encoding them, and methods of making and using these polynucleotides and polypeptides. In one aspect, the invention is directed to polypeptides, e.g., enzymes, having a hydrolase activity, e.g., an esterase, acylase, lipase, phospholipase (e.g., phosphlipase A, B, C and D acitvity, patatin activity, lipid acyl hydrolase (LAH) activity) or protease activity, including thermostable and thermotolerant hydrolase activity, and polynucleotides encoding these enzyme, and making and using these polynucleotides and polypeptides. The hydrolase activities of the polypeptides and peptides of the invention include esterase activity, lipase activity (hydrolysis of lipids), acidolysis reactions (to replace an esterified fatty acid with a free fatty acid), transesterification reactions (exchange of fatty acids between triglycerides), ester synthesis, ester interchange reactions, phospholipase activity and protease activity (hydrolysis of peptide bonds). The polypeptides of the invention can be used in a variety of pharmaceutical, agricultural and industrial contexts, including the manufacture of cosmetics and nutraceuticals. In another aspect, the polypeptides of the invention are used to synthesize enantiomerically pure chiral products.
- -
-
Page/Page column 225; 14/138
(2008/06/13)
-
- Design of well balanced hydrophilic-lipophilic catalytic surfaces for the direct and selective monoesterification of various polyols
-
The transesterification process is a well known reaction of organic chemistry. However, the monoesterification of unprotected polyols such as glycerol or sucrose is much more complex and the design of selective catalysts is becoming a huge challenge in order to avoid many protection and deprotection steps, harmful for the cost and the environmental impact of the resulting process. In this study, we showed that the control of the hydrophilic-lipophilic balance of heterogeneous catalysts is a crucial key in order to tune both the catalyst activity and the monoester selectivity. Indeed, whereas homogeneous guanidine led to low selectivity toward monoesters, its anchorage on a hydrophilic solid support such as silica allowed us to prepare two basic hybrid organic-inorganic materials able to selectively afford monoesters in high yield and in an environmentally-friendly process, at low temperature and starting from an equimolecular mixture of unprotected polyols and various fatty methyl esters. The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2005.
- Kharchafi, Ghizlane,Jerome, Francois,Adam, Isabelle,Pouilloux, Yannick,Barrault, Joel
-
p. 928 - 934
(2007/10/03)
-
- Lipase-Catalyzed Synthesis of Structured Triacylglycerides from 1,3-Diacylglycerides
-
A new method for the lipase-catalyzed synthesis of structured TAG (ST) is described. First, sn1,3-dilaurin or -dicaprylin were enzymatically synthesized using different published methods. Next, these were esterified at the sn2-position with oleic acid or its vinyl ester using different lipases. Key to successful enzymatic synthesis of ST was the choice of a lipase with appropriate FA specificity, i.e., one that does not act on the FA already present in the sn1,3-DAG, but that at the same time exhibits high selectivity and activity toward the FA to be introduced. Reactions were performed in the presence of organic solvents or in solvent-free systems under reduced pressure. With this strategy, mixed ST containing the desired compounds 1,3-dicapryloyl-2-oleyl- glycerol or 1,3-dilauroyl-2-oleyl-glycerol (CyOCy or LaOLa) were obtained at 87 and 78 mol% yield, respectively, using immobilized lipases from Burkholderia cepacia (Amano PS-D) in n-hexane at 60°C. However, regiospecific analysis with porcine pancreatic lipase indicated that in CyOCy, 25.7% caprylic acid and in LaOLa 11.1 % lauric acid were located at the sn2-position. Oleic acid vinyl ester was a better acyl donor than oleic acid. Esterification of sn1,3-DAG and free oleic acid gave very low yield (50%) in a solvent-free system under reduced pressure.
- Wongsakul, Sirirung,H-Kittikun, Aran,Bornscheuer, Uwe T.
-
p. 151 - 155
(2007/10/03)
-
- Acid-catalyzed intra- and intermolecular acyl exchange in mono- and diglycerides
-
Acid-catalyzed transformation of 1-monolauroylglycerine (1-MLG) was investigated. It has been demonstrated that 1-MLG disproportionates readily and quickly into a mixture of 1,2- and 1,3-diacylglycerines and glycerine. The transformation of 1,3-diglycerides into 1,2-diglycerides was studied.
- Isai,Usol'tsev,Stiba
-
p. 325 - 329
(2007/10/03)
-
- Chemoenzymatic synthesis of structured triacylglycerols by highly regioselective acylation
-
A highly efficient two-step chemoenzymatic synthesis of structured triacylglycerols comprising a pure n-3 polyunsaturated fatty acid at the mid-position and a pure saturated fatty acid located at the end-positions is described. In the first step an immobilized Candida antarctica lipase was observed to display an excellent regioselectivity toward the end-positions of glycerol at 0-4°C using vinyl esters as acylating agents. The n-3 fatty acids were introduced into the remaining mid-position highly efficient and in excellent yields using EDCI coupling agent.
- Halldorsson, Arnar,Magnusson, Carlos D.,Haraldsson, Gudmundur G.
-
p. 9101 - 9109
(2007/10/03)
-
- Chemoenzymatic synthesis of structured triacylglycerols
-
Six regioisomerically pure structured triacylglycerols possessing a medium-chain fatty acid (C8, C10 or C12) at the primary positions and pure eicosapentaenoic acid or docosahexaenoic acid at the secondary position of the glycerol moiety were prepared in two steps by a chemoenzymatic approach using lipase.
- Halldorsson, Arnar,Magnusson, Carlos D,Haraldsson, Gudmundur G
-
p. 7675 - 7677
(2007/10/03)
-
- Enzymatic synthesis of symmetrical 1,3-diacylglycerols by direct esterification of glycerol in solvent-free system
-
1,3-Diacylglycerols were synthesized by direct esterification of glycerol with free fatty acids in a solvent-free system. Free fatty acids with relatively low melting points (45°C) such as unsaturated and medium-chain saturated fatty acids were used. With stoichiometric ratios of the reactants and water removal by evaporation at 3 mm Hg vacuum applied at 1 h and thereafter, the maximal 1,3-diacylglycerol content in the reaction mixture was: 84.6% for 1,3-dicaprylin, 84.4% for 1,3-dicaprin, 74.3% for 1,3-dilinolein, 71.7% for 1,3-dieicosapentaenoin, 67.4% for 1,3-dilaurin, and 61.1% for 1,3-diolein. Some of the system's parameters (temperature, water removal, and molar ratio of the reactants) were optimized for the production of 1,3-dicaprylin, and the maximal yield reached 98%. The product was used for the chemical synthesis of 1,3-dicapryloyl-2-eicosapentaenoylglycerol. The yield after purification was 42%, and the purity of the triacylglycerol was 98% (both 1,3-dicapryloyl-2-eicosapentaenoylglycerol and 1,2-dicapryloyl-3-eicosapentaenoylglycerol included) by gas chromatographic analysis, of which 90% was the desired structured triacylglycerol (1,3-dicapryloyl-2-eicosapentaenoylglycerol) as determined by silver ion high-performance liquid chromatographic analysis.
- Rosu, Roxana,Yasui, Mamoru,Iwasaki, Yugo,Yamane, Tsuneo
-
p. 839 - 843
(2007/10/03)
-
- Mesoporous sulfonic acids as selective heterogeneous catalysts for the synthesis of monoglycerides
-
Glycerol was esterified with an equimolar amount of lauric acid to monolaurin using zeolites, sulfonic resins, and sulfonic mesoporous materials as catalysts. The latter were obtained by immobilization of 3-mercaptopropyl groups and oxidation with H2O2. In particular, fatty acid conversions, monoglyceride yields, and selectivities obtained with mesoporous (ordered, amorphous) sulfonic catalysts were compared with those of other heterogeneous or homogeneous catalysts.When using silica gel coated with propylsulfonic acids, high reaction rates are coupled to high monoglyceride yields, e.g., 53% mono yield for a 1:1 glycerol:lauric acid ratio. Minimizing the autocatalytic contribution of the fatty acid reactant is a critical issue. The influence of a number of reaction parameters is investigated. The mesoporous sulfonic catalysts are also employed in the esterification of propanediols and meso-erythritol, and for reactions with other fatty acids.
- Bossaert, Wim D.,De Vos, Dirk E.,Van Rhijn, Wim M.,Bullen, Joren,Grobet, Piet J.,Jacobs, Pierre A.
-
p. 156 - 164
(2007/10/03)
-
- Prostaglandin derivatives
-
Prostaglandin E1 ester derivatives of the formula (I): STR1 wherein the R' groups are the same as each other and are C4-12 alkyl; or cyclodextrin clathrates thereof, liposome formulations containing them, and pharmaceutical compositions containing them, as active ingredient. The compounds of formula (I) have the effect of increasing blood flow and are useful for the prevention and/or treatment of peripheral circulatory disorder, decubitus, or skin ulcers, or for the maintenance of blood flow.
- -
-
-
- Preparation of a Lipid-Coated Lipase and Catalysis of Glyceride Ester Syntheses in Homogeneous Organic Solvents
-
A lipid-coated lipase was prepared by mixing aqueous solutions of lipase and dialkyl amphiphiles: A hydrophilic surface of the enzyme is converted with a lipid layer, of which lipophilic two-long-alkyl tails solubilize the enzyme in hydrophobic organic solvents.The lipid-coated lipase was prepared in various conditions by changing hydrophilic head groups of lipid molecules, a ratio of lipid/lipase, and an origin of lipase; the complex prepared from nonionic amphiphiles and lipase D from Rhizopus delemar showed a high stability and a high enzymatic activity in hydrophobic organic solutions.The lipid-coated lipase catalyzed di- and triacylglycerol syntheses from monoacylglycerols and aliphatic acids in the homogeneous and dry benzene solution in the presence of two pieces of molecular sieves (water: 80 ppm). the lipid-coated lipase could also catalyze ester exchange reactions in organic solvents with a small amount of water (250 ppm).Enzymatic activity was effected by a nature of organic solvents and a water content in organic solvents.The catalytic activity of the lipid-coated lipase was highly efficient compared with other enzyme systems such as the poly(ethylene glycol)-grafted lipase and the direct dispersion of lipase powder for glyceride syntheses in the dry organic solution.
- Okahata, Yoshio,Ijiro, Kuniharu
-
p. 2411 - 2420
(2007/10/02)
-
- Glycerides with anti-inflammatory properties
-
Triglycerides carrying the anti-inflammatory drug moiety in the 2-position and hydrocarbon acyl moieties in the 1- and 3-position exhibit excellent anti-inflammatory properties without causing the side effects often associated with the anti-inflammatory drug itself.
- -
-
-