22610-63-5Relevant academic research and scientific papers
Synthesis and analysis of symmetrical and nonsymmetrical disaturated/monounsaturated triacylglycerols
Adlof, Richard O.,List, Gary R.
, p. 2096 - 2099 (2003)
Symmetrical disaturated triacylglycerols of the structure SUS, where S is stearic acid (18:0) and U is an unsaturated fatty acid, either oleic (O; 9cis-18:1), linoleic (L; 9cis, 12cis-18:2), or linolenic (Ln; 9cis, 12cis, 15cis-18:3), are important components providing functionality to interesterified fat blends and structurally modified oils. Nonsymmetrical triacylglycerols of the structure SSU can significantly change melting point and solid fat content profiles. To characterize the physical properties of pure and symmetrical and nonsymmetrical triacylglycerol mixtures, the same reaction sequence has been used to prepare multigram quantities of triacylglycerols SUS and SSU. Tristearin was converted to a mixture of mono-, di-, and triacylglycerols, and the 1,3- and 1,2-diacylglycerol fraction was isolated by silica column chromatography. The 1,3-diacylglycerols were removed by crystallization from acetone and esterified with the appropriate fatty acid to form the symmetrical triacylglycerols with >99% SUS structure. The more difficult to obtain 1,2-diacylglycerols were prepared by esterification of the enriched 1,2-diacylglycerol fraction (80-86% 1,2-diacylglycerols) remaining after removal of much of the 1,3-isomer by crystallization, but silver resin or silver nitrate impregnated silica gel chromatography was required to isolate the nonsymmetrical triacylglycerols. SSL and SSLn were prepared in purities of >98% by this procedure, but not SSO. Silver ion HPLC was found to be as accurate as, and more rapid than, lipolysis/gas chromatography for the determination of the isomeric purities of the synthesized triacylglycerols.
Homogeneous Tubular-Flow Process for Monoolein Preparation
Herskowitz, Moti,Landau, Miron V.,Koukouliev, Slava,Zarchin, Ruby,Nehemya, Roxana Vidruk,Wee, Lik H.,Martens, Johan A.
, p. 1525 - 1529 (2015)
Esterification of fatty acids with glycerol is characterized by negligible solubility of the two liquid phases. The reactions to mono-, di- and triglycerides taking place in the fatty acid phase, are limited by chemical equilibrium. The scope of this study is to investigate in a tubular reactor the conversion of a homogeneous mixture of oleic acid and glycerol in tert-butanol. The liquid composition in this study was 1 mol of oleic acid, 6 mol of glycerol and 14 mol of tert-butanol. Experiments were conducted in a tubular reactor at 35 atm over a temperature range of 200-240 °C and residence times of 0.7-17.6 h to determine the kinetics and the chemical equilibrium. The selectivity to monoolein was >95 mol %. A reversible second order reaction fits the data well.
Boronic acid-promoted site-selective Fischer esterifications of sugar alcohols
Manhas, Sanjay,Lin, Yu Chen,Wang, Grace,Kyne, Luke T.,Taylor, Mark S.
, p. 5363 - 5367 (2019)
A protocol for selective monoesterification of glycerol and pentose alcohols with fatty acids is described, using phenylboronic acid as a phase-transfer reagent. Formation of arylboronic ester intermediates serves both to increase the solubility of the alcohol substrate in nonpolar organic solvent and to selectively protect diol groups, allowing for efficient and selective condensation with the aliphatic carboxylic acid. A phase-switching workup with basic aqueous sorbitol solution is used to cleave the boronic ester groups and to separate the boronic acid from the monoester product. The method provides an operationally simple means of access to a class of bio-derived products that have been broadly applied as food additives, components of cosmetic products and pharmaceutical formations, plasticizers, and non-ionic surfactants.
Kinetic and docking study of synthesis of glyceryl monostearate by immobilized lipase in non-aqueous media
Bhanage, Bhalchandra M.,Jawale, Priyanka V.
, (2021/12/21)
Glyceryl monostearate is extensively used as an emulsifier in many industries. Mono acylation of glycerol was carried out by utilizing immobilized Candida antarctica lipase B (Cal B) as a biocatalyst and vinyl stearate as an acyl donor. Different reaction parameters, such as selection of lipases from various sources (like Candida antarctica, Candida rugosa, and Mucor meihei) and their quantity, shaking speed, temperature, substrate concentration, and reusability were studied in detail to achieve excellent conversion. Overall, 98% conversion of glycerol was obtained at a mole ratio of 1:1 of glycerol to vinyl stearate, using 12 mg of immobilized Cal B at 45 °C for 3 h. The mechanism of the given reaction was anticipated based on the results of the Lineweaver-Burk plots. It was found that the reaction followed the Ping-Pong Bi Bi mechanism with inhibition of glycerol. As it was a kinetically controlled synthesis, different kinetic constants were estimated by non-linear regression analysis. The activation energy for Cal B was found to be 10.3 kcal/mol. Further, biocatalyst can be reused up to four catalytic cycles with an average four percent loss of activity. A molecular docking study was done to find out the confirmation of substrates and their binding positions in an enzyme. It was noticed that the reaction proceeds through acyl-enzyme complex formation followed by the transfer of that acyl group to another substrate.
High-selectivity synthesis method of long-chain fatty acid monoglyceride
-
Paragraph 0035; 0038, (2019/02/27)
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.
Method for synthesizing high-content fatty acid monoglyceride and co-producing nano SiO2
-
Paragraph 0039; 0042; 0043, (2019/03/28)
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.
Method for synthesizing high content of fatty acid monoglyceride production of nano TiO2 The method of (by machine translation)
-
Paragraph 0039; 0042; 0043, (2019/03/28)
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)
Biochemical characterization of the PHARC-associated serine hydrolase ABHD12 reveals its preference for very-long-chain lipids
Joshi, Alaumy,Shaikh, Minhaj,Singh, Shubham,Rajendran, Abinaya,Mhetre, Amol,Kamat, Siddhesh S.
, p. 16953 - 16963 (2018/11/21)
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.
A glycerol monostearate synthesis method catalyzed by roasted hydrocalumite
-
Paragraph 0017; 0018; 0019; 0020; 0021, (2019/01/08)
A glycerol monostearate synthesis method catalyzed by roasted hydrocalumite is disclosed. Glycerol monostearate is synthesized from methyl stearate and glycerol under the catalytic function of the roasted hydrocalumite. The hydrocalumite is synthesized from Ca(OH)2 and Al(OH)3 in a clean manner and is roasted to obtain a roasted hydrocalumite catalyst. The method has advantages of a low catalyst cost, a simple and clean preparation process, high product selectivity and easy separation of the catalyst from a product.
Glyceryl monostearate preparation method
-
Paragraph 0023; 0024; 0025; 0026; 0027; 0028; 0029-0042, (2017/06/29)
The invention belongs to the technical field of chemical synthesis, and relates to a glyceryl monostearate preparation method. Raw materials including stearic acid and glycerol carbonate are subjected to esterification reaction under the action of esterification catalysts and subjected to washing, reflux and chromatography to obtain intermediate products. The intermediate products and water are subjected to basic hydrolysis reaction under the action of hydrolysis catalysts and subjected to reflux, chromatography and decompression drying to obtain glyceryl monostearate. Compared with the prior art, the preparation method has the advantages that the purity of the obtained glyceryl monostearate can reach 93% or more, and the yield of the glyceryl monostearate can reach 90% or more under the condition of the preparation process superior to a traditional preparation process. Moreover, the production process is simple, the chemical principle is reliable, reaction conditions are mild, production equipment is simple, operation conditions are simple, product quality is good, the yield is high, investment cost is low, economic benefits are good, the whole production process is high in controllability, and industrial production is easily realized.
