cas 40738-26-9, MONOLAURIN | Articles data

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Lipase-catalyzed two-step esterification for solvent-free production of mixed lauric acid esters with antibacterial and antioxidative activities
Mixed lauric acid esters (MLE) with antibacterial and antioxidative activities were produced through lipase-catalyzed two-step esterification in solvent-free system without purification. In the first reaction, erythorbyl laurate was synthesized for 72 h. Successive reaction for 6 h at molar ratio of 1.0 (lauric acid to glycerol) produced MLE containing erythorbyl laurate and glyceryl laurate with small amounts of residual substrates, by converting 99.52% of lauric acid. MLE addition (0.5–2.0%, w/w) to Tween 20-stabilized emulsions decreased droplet size, polydispersity index, and zeta-potential, possibly enhancing the emulsion stability. In the emulsions, MLE at 0.5 and 2.0% (w/w) caused 4.4–4.6 and 5.9–6.1 log reductions of Gram-positive (Staphylococcus aureus, Listeria monocytogenes) and Gram-negative bacteria (Escherichia coli, Pseudomonas aeruginosa), respectively, within 12 h. Lipid hydroperoxide concentrations decreased to 50.8–98.3% in the presence of 0.5–2.0% (w/w) MLE. These findings support a novel approach without needing purification to produce multi-functional food additives for emulsion foods.
Yu, Hyunjong,Byun, Yerim,Chang, Pahn-Shick
(2021/08/01)

Preparation method of glycerol monolaurate
The invention provides a preparation method of glycerol monolaurate, and belongs to the field of organic synthesis. According to the method, lauric acid and glycerol are used as raw materials, the glycerol esterification reaction of long-chain fatty acid lauric acid is catalyzed through an acid catalyst, and an eutectic solvent is used as a solvent, so that the activation energy of the esterification reaction can be reduced, the esterification reaction can be carried out at a relatively low temperature, and meanwhile, the eutectic solvent is easily separated from and recycled from a product; and on one hand, hydroxyl on a glycerol structure can be protected, esterification reaction is promoted to directionally and selectively generate glycerol monolaurate, and generation of a byproduct diester is inhibited, so that the selectivity, the yield and the purity of the product glycerol monolaurate are improved. The result of the embodiment shows that the glycerol monolaurate can be prepared at the low temperature of 120-160 DEG C by utilizing the method provided by the invention, the product selectivity is 87.1%, the yield is 76.4%, and the purity is 89.4%.
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Paragraph 0052; 0057-0112

(2021/08/07)

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
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Paragraph 0076-0078

(2020/08/18)

High-selectivity synthesis method of long-chain fatty acid monoglyceride
The invention belongs to the field of fatty acid and synthetic fatty acid glycerides and relates to a high-selectivity synthesis method of long-chain fatty acid monoglyceride, in particular to a high-selectivity synthesis method of long-chain fatty acid and synthetic fatty acid glycerides. The method comprises the steps that tetraethyl silicate and glycerin are subjected to alcoholysis reaction, and part of glycerin is esterified to generate glyceryl silicate; then the glyceryl silicate is subjected to esterification reaction with fatty acid to generate fatty acid glyceride; finally the high activity (instability) of silicate ester is utilized to achieve hydrolysis under mild conditions to synthesize the synthetic fatty acid glyceride at high selectivity. A by-product is safe and harmlessSiO2. Accordingly, the product with high monoglyceride content is obtained by using a simple process under mild conditions.
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Paragraph 0023; 0026

(2019/02/27)

Method for synthesizing high-content fatty acid monoglyceride and co-producing nano SiO2
The invention belongs to the field of fatty acid glyceride synthesis and nano powder preparation, relates to a method for synthesizing high-content fatty acid monoglyceride and co-producing nano SiO2,and particularly relates to a method for synthesizing fatty acid monoglyceride and co-producing the nano SiO2 by long-chain fatty acid and glycerinum. The method comprises the following steps of: using silicon tetrachloride to react with the glycerinum, so as to enable the glycerinum to be partially esterified to generate silicic acid glyceride; and performing an esterification reaction with fatty acid to generate fatty acid silicic acid glyceride; finally using high-activity (instability) of silicate ester, hydrolyzing in a mild condition, synthesizing the high-content fatty acid monoglyceride, and by-producing SiO2 powder in a nano state. So that a fatty acid monoglyceride product is high-selectively obtained and nano SiO2 powder is co-produced by a simple technology in the mild condition.
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Paragraph 0029; 0032; 0033

(2019/03/28)

Method for synthesizing high content of fatty acid monoglyceride production of nano TiO2 The method of (by machine translation)
The invention belongs to the fatty acid glyceride synthesis and nano powder preparation field. In particular to fatty acid and glycerin synthesis of fatty acid monoglyceride, and cogeneration nano TiO2 Method. Method of this invention is: for the reaction of titanium tetrachloride and glycerin, glycerol partial esterification, generating titanate glycerides. Then with the fatty acid esterification reaction, to generate fatty acid glyceride titanate. Finally the use of a titanate high activity (instability), hydrolysis under mild conditions, synthesizing high-content fatty acid monoglyceride, the pressure of the by-product TiO2 Powder. Thus a simple process, under mild conditions, a high content of fatty acid monoglyceride product, production of nano TiO2 Powder. (by machine translation)
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Paragraph 0029; 0032; 0033

(2019/03/28)

Synthesis and antibacterial activity of 1-monolaurin
An improvement of method for synthesizing 1-monolaurin from lauric acid and glycerol has been done. The reaction was carried on mol ratio between lauric acid and glycerol 1:1 at 130 °C for 6 h with variation of pTSA catalyst of 2.5%, 5%, 7.5% (w/w of lauric acid). The purification of 1-monolaurin was conducted only by extracting with alcoholic solution. The product of 1-monolaurin was obtained as a white solid with 100% of purity from variation of 2.5% and 5% of pTSA catalyst with 43.54% and 27.89% yield, respectively. 1-Monolaurin could inhibit the growth of S. aureus and E. coli bacteria at 500 μg/mL of concentration.
Nitbani, Febri Odel,Jumina,Siswanta, Dwi,Sholikhah, Eti Nurwening,Fitriastuti, Dhina
p. 863 - 867
(2018/05/28)

Biochemical characterization of the PHARC-associated serine hydrolase ABHD12 reveals its preference for very-long-chain lipids
Polyneuropathy, hearing loss, ataxia, retinitis pigmentosa, and cataract (PHARC) is a rare genetic human neurological disorder caused by null mutations to the Abhd12 gene, which encodes the integral membrane serine hydrolase enzyme ABHD12. Although the role that ABHD12 plays in PHARC is understood, the thorough biochemical characterization of ABHD12 is lacking. Here, we report the facile synthesis of mono-1-(fatty)acyl-glycerol lipids of varying chain lengths and unsaturation and use this lipid substrate library to biochemically characterize recombinant mammalian ABHD12. The substrate profiling study for ABHD12 suggested that this enzyme requires glycosylation for optimal activity and that it has a strong preference for very-long-chain lipid substrates. We further validated this substrate profile against brain membrane lysates generated from WT and ABHD12 knockout mice. Finally, using cellular organelle fractionation and immunofluorescence assays, we show that mammalian ABHD12 is enriched on the endoplasmic reticulum membrane, where most of the very-long-chain fatty acids are biosynthesized in cells. Taken together, our findings provide a biochemical explanation for why very-long-chain lipids (such as lysophosphatidylserine lipids) accumulate in the brains of ABHD12 knockout mice, which is a murine model of PHARC.
Joshi, Alaumy,Shaikh, Minhaj,Singh, Shubham,Rajendran, Abinaya,Mhetre, Amol,Kamat, Siddhesh S.
p. 16953 - 16963
(2018/11/21)

Ionic Liquid–Silicotungstic Acid Composites as Efficient and Recyclable Catalysts for the Selective Esterification of Glycerol with Lauric Acid to Monolaurin
The synthesis of glycerol monolaurate (GML) by the esterification of glycerol (GL) with lauric acid (LA) over a series of propyl sulfonic acid-functionalized ionic liquids (SAFILs)-modified silicotungstic acid (STA; H4SiW12O40) composite catalysts has been investigated. The synthesized organic–inorganic hybrid catalysts were characterized by different physicochemical techniques. In particular, their acidic properties were studied by solid-state 31P magic angle spinning (MAS) NMR spectroscopy by using adsorbed trimethylphosphine oxide (TMPO) as a probe. The effects of key reaction parameters, such as glycerol/lauric acid molar ratio, amount of catalyst, reaction time, and reaction temperature on LA conversion and GML product yield were elucidated and optimized with response surface methodology (RSM). The N,N-dimethyl(benzyl)ammonium propyl sulfobetaine (DMBPS)-modified STA [DMBPSH]H3SiW12O40 exhibited the optimal catalytic activity and was exploited for process optimization. A highest GML yield of 79.1 % was achieved with the optimized reaction conditions. The high catalytic activity of these hybrid catalysts were attributed to strong acidity, low transport resistance, and their “pseudoliquid” characteristics. A kinetic study was made based on a second-order irreversible model of the esterification reaction, which resulted in an activation energy of 39.49 kJ mol?1 for [DMBPSH]H3SiW12O40 under optimized reaction conditions.
Han, Xiaoxiang,Zhang, Xiaofang,Zhu, Guangqi,Liang, Juanjuan,Cao, Xianghui,Kan, Renjun,Hung, Chin-Te,Liu, Li-Li,Liu, Shang-Bin
p. 2727 - 2738
(2017/07/28)

Preparation method of glycerol laurate
The invention relates to the field of chemical synthesis, in particular to a preparation method of glycerol laurate. The preparation method of glycerol laurate comprises steps as follows: low sodium alcoholate or low potassium alcoholate is taken as a catalyst, low alcohol fatty acid ester and glycerol are mixed in the mole ratio of 3:1, the mixture reacts under a vacuum condition at the temperature of 150-170 DEG C for 20-40 h, and a crude glyceride product is obtained; the crude glyceride product is subjected to follow-up processing, and a corresponding product is obtained. The preparation method has a remarkable function on increase of productivity and improvement of quality in a solvent-free system, and the content of glycerol monolaurate in the product is high.
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Paragraph 0015-0017

(2017/07/07)

Highly selective biocatalytic synthesis of monoacylglycerides in sponge-like ionic liquids
The biocatalytic synthesis of monoacylglycerides (MAGs) was carried out by the direct esterification of fatty acids (i.e. capric, lauric, myristic, palmitic and oleic acids, respectively) with glycerol in different ionic liquids (ILs) based on cations with long alkyl side-chains (e.g. 1-hexadecyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide [C16mim][NTf2], 1-dodecyl-3-methylimidazolium tetrafluoroborate [C12mim][BF4], etc.). Although all ILs have been shown as suitable reaction media for Novozym 435-catalyzed esterification of glycerol with free fatty acids, a high selectivity of MAGs was only observed in the [C12mim][BF4] case (e.g. up to 100% selectivity and 100% yield for monolaurin). Furthermore, as these ILs are temperature switchable ionic liquid/solid phases that behave as sponge-like systems, a straightforward protocol for IL-free MAG recovery, based on iterative centrifugations at controlled temperature, has been developed.
Lozano, Pedro,Gomez, Celia,Nieto, Susana,Sanchez-Gomez, Gregorio,García-Verdugo, Eduardo,Luis, Santiago V.
p. 390 - 396
(2017/08/14)

Preparation method for high-purity glyceryl monolaurate
The invention provides a preparation method for high-purity glyceryl monolaurate. The preparation method comprises the steps of: mixing lauric acid, glycerinum and a catalyst to obtain a mixed liquid; preheating the mixed liquid; then adding the heated mixed liquid into a vacuum reaction for reaction; after reaction, obtaining a coarse ester; quickly cooling the coarse ester to 120-150 DEG C; filtering the coarse ester to obtain the supernatant so as to obtain the glyceryl monolaurate with the purity of 35-45%; and finally, performing four-stage distillation to obtain the glyceryl monolaurate with the purity of 85-95%.
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Paragraph 0023

(2016/10/17)

LDH-catalyzed esterification of lauric acid with glycerol in solvent-free system
Direct esterification of waste oil materials (high FFA contents) and glycerol can be an important way to improve the energy goals and afford alternative sources to emulsifier production for food and cosmetics industry. This work reports an experimental study of free-solvent esterification of lauric acid with glycerol using a LDH (layered double hydroxide, Mg-Al-CO3) as catalyst. The experiments were performed in a mechanically stirred reactor evaluating the effect of temperature (100-180 C), lauric acid to glycerol molar ratio (1:1-3:1) and catalyst content (2-8 wt%). The results showed that relative high glycerol conversions (99%) can be obtained for the lauric acid esterification with glycerol leading to monolaurine and dilaurine. Results show that free-solvent LDH-catalyzed lauric acid esterification with glycerol might be a potential alternative route to conventional methods, as high contents of reaction products and selectivity was achieved. Furthermore, the results show that the LDH catalyst used was able to drive the reaction to the equilibrium in a relative short time - up to two hours.
Hamerski, Fabiane,Corazza, Marcos L.
p. 242 - 248
(2014/03/21)

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)

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.
p. 55 - 63
(2013/10/22)

The chemical synthesis and cytotoxicity of new sulfur analogues of 2-methoxy-lysophosphatidylcholine
The chemical synthesis of phosphorothioate/phosphorodithioate analogues of 2-methoxy-lysophosphatidylcholine has been described. For the preparation of new sulfur derivatives of lysophosphatidylcholine both oxathiaphospholane and dithiaphospholane approaches have been employed. Each lysophospholipid analogue was synthesized as a series of five compounds, bearing different fatty acid residues both saturated (12:0, 14:0, 16:0, 18:0) and unsaturated (18:1). The methylation of glycerol 2-hydroxyl function was applied in order to increase the stability of prepared analogues by preventing 1→2 acyl migration. The cellular toxicity of newly synthesized 2-methoxy-lysophosphatidylcholine derivatives was measured using MTT viability assay and lactate dehydrogenase release method.
Rytczak, Przemyslaw,Drzazga, Anna,Gendaszewska-Darmach, Edyta,Okruszek, Andrzej
p. 6794 - 6798
(2014/01/06)

The chemical synthesis of metabolically stabilized 2-OMe-LPA analogues and preliminary studies of their inhibitory activity toward autotaxin
The chemical synthesis of five new metabolically stabilized 2-OMe-LPA analogues (1a-e) possessing different fatty acid residues has been performed by phosphorylation of corresponding 1-O-acyl-2-OMe-glycerols which were prepared by multistep process from racemic glycidol. The now analogues were subjected to biological characterization as autotaxin inhibitors using the FRET-based, synthetic ATX substrate FS-3. Among tested compounds 1-O-oleoyl-2-OMe-LPA (1e) appeared to be the most potent, showing ATX inhibitory activity similar to that of unmodified 1-O-oleoyl-LPA. Parallel testing showed, that similar trend was also observed for corresponding 1-O-acyl-2-OMe-phosphorothioates (2a-e, synthesized as described by us previously). 1-O-oleoyl-2-OMe-LPA (1e) was found to be resistant toward alkaline phosphatase as opposed to unmodified 1-O-oleoyl-LPA.
Gendaszewska-Darmach, Edyta,Laska, Edyta,Rytczak, Przemys?aw,Okruszek, Andrzej
supporting information; body text
p. 2698 - 2700
(2012/05/20)

Pore size control and organocatalytic properties of nanostructured silica hybrid materials containing amino and ammonium groups
Periodic mesoporous organosilicas containing amine and ammonium substructures were synthesized via soft templating approaches using anionic surfactants. Pore size control was achieved either using anionic surfactants containing alkyl groups of variable chain lengths or by addition of swelling agents such as mesitylene (1,3,5-trimethylbenzene, TMB) to the hydrolysis-polycondensation mixture. The addition of mesitylene allows to increase the pore size in the materials from 2 to 6 nm. The materials appear as versatile and recyclable heterogeneous organocatalysts in Knoevenagel and Henry reactions and in the formation of monoglycerides by ring opening reaction of glycidol. This study highlights the huge potential of silica hybrid materials containing ionic substructures (i-silica) materials in heterogeneous catalysis.
El Hankari, Samir,Motos-Perez, Blanca,Hesemann, Peter,Bouhaouss, Ahmed,Moreau, Joel J. E.
experimental part
p. 6948 - 6955
(2011/11/28)

Preparation of diacid 1,3-diacylglycerols
A complete methodology (including synthesis, purification and analysis) for the preparation of 1,3-DAG is described. For a successful synthesis project, the strengths and weaknesses of each particular process should be taken into account and measures taken to offset or balance potential weaknesses. To this end, we describe some of the challenges associated with: chemically and enzymatically catalyzed acylglycerol syntheses; recrystallization and flash chromatography for purification of partial acylglycerols; and thin-layer chromatography (TLC) separation of DAG. For this work, 1-MAG intermediates and subsequent diacid 1,3-DAG were prepared using non-enzymatic methods, whereas, monoacid 1,3-DAG were prepared by enzymatic methods. It was not always possible to obtain pure samples of target compounds-in recrystallizations this is due to solid solution formation and co-crystallization and in chromatographic separations it is due to co-elution of components with similar Rf. Furthermore, TLC Rf of DAG is determined by two main factors: acyl chain length and positional isomerism. Interestingly, while the role of positional isomerism is well-known, the role of acyl chain length in these separations has only recently come to light.
Craven, R. John,Lencki, Robert W.
p. 1281 - 1291
(2011/08/21)

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)

The chemical synthesis of phosphorothioate and phosphorodithioate analogues of lysophosphatidic acid (LPA) and cyclic phosphatidic acid (CPA)
The chemical synthesis of new sulfur analogues of lysophospholipids has been described, including phosphorothioate/phosphorodithioate derivatives of lysophosphatidic acids (LPA) and phosphorothioate/phosphorodithioate derivatives of cyclic phosphatidic acids (cPA). For the preparation of LPA and cPA derivatives both oxathiaphospholane and dithiaphospholane approaches have been employed. Each lysophospholipid analogue has been synthesized as a series of five compounds, bearing five different fatty acid residues, both saturated (12:0, 14:0, 16:0, 18:0) and unsaturated (18:1), in the form of ammonium salts. The phosphorodithioate analogues of LPA were obtained as triethylammonium salts, however these were not stable and decomposed when transformed into the ammonium salt by ion exchange in aqueous methanol solution. The new sulfur analogues of LPA and cPA may share interesting biological properties of their parent compounds, and previously synthesized derivatives may behave as regulators of many metabolic processes and hopefully show new biological activity.
Rytczak, Przemyslaw,Koziolkiewicz, Maria,Okruszek, Andrzej
experimental part
p. 1008 - 1017
(2010/08/05)

Efficient synthesis of α-monoglycerides via solventless condensation of fatty acids with glycerol carbonate
Highly pure α-monoglycerides (5a-e) were successfully prepared in high yields by the condensation of fatty acids such as lauric, myristic, palmitic, stearic and oleic (2a-e) with glycerol carbonate (4-hydroxymethyl-1,3- dioxolan-2-one) (1) in the presence
Ghandi, Mehdi,Mostashari, Abdoljalil,Karegar, Mojgan,Barzegar, Mina
p. 681 - 685
(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.
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Page/Page column 5

(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)

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.
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Page/Page column 227-228; 21/138

(2008/06/13)

Lipase-mediated desymmetrization of glycerol with aromatic and aliphatic anhydrides
Chirazyme L-2 (Candida antarctica) catalyzed esterification of glycerol with aromatic and aliphatic anhydrides in 1,4-dioxane is described. All the aromatic monoacylglycerols (MAGs) were produced as (R)-enantiomers, while aliphatic MAGs were obtained either as racemic mixtures or the (S)-enantiomers. The influence of substituted aromatic rings, chain length, and presence of a conjugated double bond in the acyl donor moiety on the enantiotopic selectivity as well as the efficiency of the enzyme was studied.
Batovska, Daniela I.,Tsubota, Shuichirou,Kato, Yasuo,Asano, Yasuhisa,Ubukata, Makoto
p. 3551 - 3559
(2007/10/03)

Lipase-catalyzed alcoholysis of triglycerides for short-chain monoglyceride production
Lipase from Pseudomonas fluorescens efficiently catalyzed the alcoholysis of various TG in dry alcohols. For TG with short-chain FA, more MG were accumulated. The yields of MG were affected by the alcohols used. The maximum yields of MG were as follows: 8
Lee, Guan-Chiun,Wang, Dong-Lin,Ho, Yi-Fang,Shaw, Jei-Fu
p. 533 - 536
(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)

Development of an environmentally benign process for the production of fatty acid methyl esters
The production of fatty acid methyl esters (FAME) is an important intermediate step in oleochemistry. The oleochemical production route starts with the renewable raw materials fat and oil and ends at fatty alcohols and different special products. Fatty acid methyl esters can be formed at mild reaction temperatures by transesterification of natural triglycerides (fats and oils). This contribution will show the development of a continuous process which is considering the main principles of production integrated environmental protection. The main advantages of this process are low energy consumption and minimal waste production. The process alternatives are shown and a scope on future problems which have to be solved to reach a real additional improvement of the fatty acid methyl esters production is given.
Jordan,Gutsche
p. 99 - 105
(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)

Study of the effect of DATEM. 1. Influence of fatty acid chain length on rheology and baking
To answer the question of which fatty acid residue is the most effective, diacetyltartaric esters of monoglycerides (DATEMs) with fatty acids of chain lengths 6:0-20:0 were synthesized. The activity of synthesized DATEMs and commercial DATEM products was studied by means of rheological methods and a microscale baking test with 10 g of flour. Variation of the acyl residue from 6:0 to 22:0 showed that stearic acid (18:0) had the best effect on the baking activity of DATEM (loaf volume increased by 62%). DATEMs containing unsaturated fatty acids (18:1, 18:2) or DATEMs produced from diacylglycerols instead of monoacylglycerols showed a slight increase of the loaf volumes. A slight effect of DATEM on the rheology of dough was observed. However, much greater was the effect on the gluten isolated from doughs prepared with DATEM. The resistance of gluten to extension was increased after the addition of increasing amounts of DATEM (0.1-0.5%). Within the series of DATEMs derived from the homologous series of monoacylglycerols the product based on glycerol monostearate (18:0) showed a maximum increase of the gluten resistance.
Koehler, Peter,Grosch, Werner
p. 1863 - 1869
(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)

Monoglyceride Synthesis by Heterogeneous Catalysis Using MCM-41 Type Silicas Functionalized with Amino Groups
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Cauvel, Anne,Renard, Gilbert,Brunel, Daniel
p. 749 - 751
(2007/10/03)

Method of encapsulation and microcapsules produced thereby
Microcapsules are prepared by dispersing or dissolving an active component or components in a solid matrix-forming material that has been thermally softened to form an encapsulation composition. The encapsulation composition is injected as an intact stream into a quenching liquid to provide solid microcapsules.
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(2008/06/13)

Kinetics of acyl migration in monoglycerides and dependence on acyl chainlength
The chemical rearrangement reaction of β- into α-monoglycerides is described. Four monoglycerides with different fatty acid chainlength have been investigated, and the equilibrium constant and the reaction velocity constants characterizing the reaction of the chemical rearrangement were estimated with a mathematical model. A 1:6.5 mixture of α/β-monoglycerides appeared to rearrange to a mixture of 1:1 α/β-monoglycerides within 24 h. Furthermore, the reaction velocity of the rearrangement reaction of β- to α-monoglycerides depended on the fatty acyl chainlength in the monoglyceride.
Boswinkel,Derksen,Van't Riet,Cuperus
p. 707 - 711
(2007/10/03)

A FACILE SYNTHESIS OF 1(3)-ACYLGLYCEROLS
A facile route is described for the synthesis of 1(3)-acylglycerols for the first time through hydroxylation of allyl esters of fatty acids with the novel reagent cetyltrimethylammonium permanganate in a non-aqueous medium.
Gangadhar, A.,Subbarao, R.,Lakshminarayana, G.
p. 2505 - 2514
(2007/10/02)