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Production of Glyceryl Monostearate by Immobilized Candida Antarctica B Lipase in Organic Media
Journal of Applied Biotechnology & Bioengineering Research Article Open Access Production of glyceryl monostearate by immobilized candida antarctica B lipase in organic media Abstract Volume 2 Issue 3 - 2017 Chemical methods of synthesizing monoglycerides (MGs) produce mixture of Kavadia MR, Yadav MG, Odaneth AA, Arvind acylglycerols making the synthesis of MGs of a single fatty acid type not possible through this route. Lipases due to their selectivity and specificity offer a useful way M Lali DBT-ICT-Centre for Energy Biosciences, India of synthesizing highly purified single fatty acid containing monoglycerides. Glyceryl monostearate (GMS), a nonionic amphiphilic monoglyceride of glycerol and stearic Correspondence: Annmmma A Odaneth, Assistant Professor acid is widely used as emulsifier in food, cosmetic, pharmaceutical and textile in Biochemistry, DBT-ICT Centre for Energy Biosciences, industry. In the present work, lipase mediated synthesis of GMS was explored using Institute of Chemical Technology, Nathalal Parikh Marg, Novozym 435 and indigenously immobilized Candida antarctica B lipase. Direct Mumbai-400 019, Mahrashtra, India, Fax +91-22-24145614, Tel esterification of glycerol and stearic acid was used as strategy and various parameters +91-22-33612312, Email [email protected] that influence synthesis of glyceryl monostearate such as molar ratio of substrates, enzyme load, reaction time and solvent polarity were systematically studied using Received: October 27, 2016 | Published: February 28, 2017 Novozym 435 lipase. Esterification efficiency of indigenously immobilized Candida antarctica B lipase and Novozym 435 was compared for synthesis of GMS and indigenously immobilized Candida antarctica B lipase gave conversion competitive to Novozym 435. Indigenously immobilized Candida antarctica B lipase in the presence of homogenous substrate solution using tert-butyl alcohol as the reaction medium, resulted in exclusive production of monoglyceride without formation of diglyceride. -
Asian Journal of Chemistry; Vol
Asian Journal of Chemistry; Vol. 26, No. 22 (2014), 7564-7568 ASIAN JOURNAL OF CHEMISTRY http://dx.doi.org/10.14233/ajchem.2014.16867 Synthesis of Glycerol Monostearate by Esterification on H3PW12O40/MCM-41 Catalyst * YI GU, LU ZHOU, LEI NIU, MEI HONG and GUOMIN XIAO School of Chemistry and Chemical Engineering, Southeast University, Nanjing 211189, P.R. China *Corresponding author: Tel: +86 25 52090612; E-mail: [email protected] Received: 12 December 2013; Accepted: 4 April 2014; Published online: 6 November 2014; AJC-16184 H3PW12O40/MCM-41 solid-acid catalyst with different phosphotungstic acid (H3PW12O40) loadings was prepared by impregnation method and used in the esterification of glycerol with stearic acid using N,N-dimethyl formamide as solvent. The catalyst was characterized by FT-IR spectroscopy, transmission electron microscopy and scanning electron microscopy. The effects of catalyst preparation and esterification parameters such as reaction time, stearic acid/glycerol ratio and reaction temperature on esterification were investigated simultaneously. The results showed that H3PW12O40/MCM-41 had the best catalytic properties when the H3PW12O40 loading was 30 % and the use of DMF had a significant improvement on the yield of monoglyceride. Under a reaction condition of 6 h, 433 K and glycerol/acid molar ratio 6:1, 91 % selectivity of glycerol monosteatate was achieved with a stearic acid conversion of 98 %. Keywords: Esterification, Glycerol monostearate, Tungstophosphoric acid, MCM-41. INTRODUCTION The direct esterification of glycerol with fatty acid in the presence of solid acid materials has attracted more and more The increasing production of biodiesel generates a great attentions in order to avoid side reactions. -
Glycerides (Mono And
Glycerides (mono and di) Handling/Processing 1 2 Identification of Substance 17 monopalmitate, glyceryl monooleate, etc; 3 Chemical Names: 18 monostearin, monopalmitin, monooliein. 4 Monoglycerides and diglycerides; 19 5 monoacylglycerol (MAG) and diacylglycerol 20 Trade Names: 6 (DAG); mono- and diglycerides of fatty acids 21 Mono and diglyceride; Mono and diglycerides; 7 22 Mono- and diglycerides of fatty acids 8 Other Name: 9 Fatty acids, edible, mono- and diglycerides; CAS Numbers: 10 Mixed mono- and diglycerides; Mono- and Various. E.g. 67254-73-3; 67701-32-0 (C14-18 and 11 diglycerides of edible fat-forming acids; Mono- C16-18-unsat.); 85251-77-0; 67784-87-6 (mono and 12 and diglycerides of edible fats and oils; Mono- diglycerides of hydrogenated palm oil); 26402-22- 13 and diglycerides of edible fatty acids; Mono- and 2, 26402-26-6 (medium chain mono- and 14 diglycerides of fat-forming fatty acids; digylcerides); 31566-31-1 (Glycerol monostearate) 15 Glyceryl mono and di-esters; glycerol 16 monostearate, glyceryl distearate; glyceryl Other Codes: INS No. 471; E471 23 24 Summary of Current Use 25 26 Glycerides (mono and di) are currently allowed in organic food processing at 7 CFR §205.605(b) for use only in 27 drum drying of food. 28 29 Characterization of Substance 30 31 Composition of the Substance: 32 Mono- and diglycerides are a class of substances which contain a mixture of mono- and diglyceryl esters of the 33 long chain fatty acids, either saturated and unsaturated, that occur in fats in food. The FDA Generally 34 Recognized As Safe (GRAS) listing notes that the substance also contains minor amounts of triesters, and is 35 prepared from fats, oils, or fat-forming acids derived from edible sources. -
12.2% 122,000 135M Top 1% 154 4,800
View metadata, citation and similar papers at core.ac.uk brought to you by CORE We are IntechOpen, provided by IntechOpen the world’s leading publisher of Open Access books Built by scientists, for scientists 4,800 122,000 135M Open access books available International authors and editors Downloads Our authors are among the 154 TOP 1% 12.2% Countries delivered to most cited scientists Contributors from top 500 universities Selection of our books indexed in the Book Citation Index in Web of Science™ Core Collection (BKCI) Interested in publishing with us? Contact [email protected] Numbers displayed above are based on latest data collected. For more information visit www.intechopen.com Chapter Monoglycerides as an Antifungal Agent Febri Odel Nitbani and Jumina Jumina Abstract Monoglyceride is a part of a lipid group compound. As a derivative of triglycer- ides, monoglycerides could be produced from renewable resources like fat or vegeta- ble oils. Structurally, monoglyceride has lipophilic and hydrophilic properties in its molecule. Lipophilic properties could be donated by an acyl group from fatty acid and hydrophilic properties from two hydroxyl residues. Therefore, it was referred to as an organic amphiphilic compound. Monoglycerides have potency as antifungal agents. Based on its chemical structure, monoglyceride allows to bind to lipid bilayer and other components on the cell membrane of fungal microorganism and damage it. In this chapter, we will describe the structure and classification, physical and chemical properties, as well as reaction path synthesis of monoglyceride from vegetable oils and mechanism of action of monoglyceride as antifungal agents. Keywords: monoglyceride, amphiphilic, antifungal, vegetable oil 1. -
Lipase Catalyzed Solvent Free Synthesis of Monoacylglycerols in Various Reaction Systems and Coupling Reaction with Pervaporation for in Situ Water Removal
Chemical Engineering & Processing: Process Intensification 166 (2021) 108475 Contents lists available at ScienceDirect Chemical Engineering and Processing - Process Intensification journal homepage: www.elsevier.com/locate/cep Lipase catalyzed solvent free synthesis of monoacylglycerols in various reaction systems and coupling reaction with pervaporation for in situ water removal Yamini Satyawali *, Lieve Cauwenberghs, Miranda Maesen, Winnie Dejonghe Separation and Conversion Technology, Flemish Institute for Technological Research (VITO), Boeretang 200, 2400 Mol, Belgium ARTICLE INFO ABSTRACT Keywords: This work reports a practical comparison of simple reaction systems for enzymatic production of mono Lipase acylglycerols (MAG) from lauric- and caprylic acid. Two approaches namely shake flasksand packed bed reactor Esterification (from 60 g to 3 kg scale) were compared as well as water removal strategies such as adsorption on molecular Process intensification sieves, N2 stripping and hydrophilic pervaporation, were studied. In all the reactor systems high fatty acid Monolaurin conversion (>90%) was achieved in solvent free conditions. The product profileobtained showed 35 wt% - 50 wt Monocaprylin Pervaporation % MAG in various systems and was related to final fatty acid conversion as well as reaction conditions and set- In situ water removal ups. The selectivity of products in the tested systems, ranged from 55 to 70 wt% mono-, 30–35 wt% di- and 1–10 Monoacylglycerol wt% triacylglycerols. Packed bed reactor enabling enzyme reuse, was -
Preparation of Fatty Acid and Monoglyceride from Vegetable
Journal of Oleo Science Copyright ©2020 by Japan Oil Chemists’ Society doi : 10.5650/jos.ess19168 J. Oleo Sci. 69, (4) 277-295 (2020) REVIEW Preparation of Fatty Acid and Monoglyceride from Vegetable Oil Febri Odel Nitbani1* , Putra Jiwamurwa Pama Tjitda2, Beta Achromi Nurohmah3, and Hermania Em Wogo1 1 Department of Chemistry, Faculty of Science and Engineering, Nusa Cendana University, INDONESIA 2 Department of Pharmacy, Health Polytechnic of Kupang, Adisucipto str., Penfui Kupang 85111, INDONESIA 3 Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Gadjah Mada, Yogyakarta, INDONESIA Abstract: Fatty acid and monoglyceride are examples of lipid compounds that can be founded in vegetable oils. The fatty acid has an important role in the human diet, lubricants, detergents, cosmetics, plastics, coatings, and resin. Monoglyceride has a wide function in the food industry in particular as natural emulsifier, pharmaceuticals, cosmetics, antioxidant, and antibacterial. Therefore, isolation and preparation of fatty acid and monoglyceride are the crucial step. This article focuses on providing the chemical reaction paths of isolation fatty acid and synthesis of monoglyceride from vegetable oils. Fatty acids could be isolated by Colgate-Emery steam hydrolysis, hydrolysis of vegetable oils using inorganic base catalyst or lipase, and base-catalyzed hydrolysis of pure fatty acid methyl ester. There are three steps in the synthesis of pure fatty acid methyl ester which are neutralization, transesterification, and fractional distillation. There are four reactions paths in preparing monoglyceride from vegetable oils. They are glycerolysis, ethanolysis using lipase enzyme (sn-1,3), esterification of fatty acid with glycerol in the presence of inorganic acid catalyst or lipase, transesterification of fatty acid methyl ester with glycerol, transesterification of fatty acid methyl ester with protected glycerol (1,2-O-isopropylidene glycerol), and deprotection using an acid resin (Amberlyst-15). -
(12) United States Patent (10) Patent No.: US 9,364,547 B2 Giliyar Et Al
US009364,547B2 (12) United States Patent (10) Patent No.: US 9,364,547 B2 Giliyar et al. (45) Date of Patent: *Jun. 14, 2016 (54) 17-HYDROXYPROGESTERONE ESTER (58) Field of Classification Search CONTAINING ORAL COMPOSITIONS AND USPC .................................................. 514/170, 182 RELATED METHODS See application file for complete search history. (71) Applicant: Lipocine Inc., Salt Lake City, UT (US) (56) References Cited (72) Inventors: Chandrashekar Giliyar, North Maple U.S. PATENT DOCUMENTS Grove, MN (US); Srinivasan Venkateshwaran, Salt Lake City, UT 3,164,520 A 1/1965 Raymond (US); Basawaraj Chickmath, 4,196,188 A 4, 1980 Besins Plymouth, MN (US); Satish Kumar (Continued) Nachaegari, Salt Lake City, UT (US); Nachiappan Chidambaram, Sandy, UT FOREIGN PATENT DOCUMENTS (US); Mahesh V. Patel, Salt Lake City, CN 1398590 A 2, 2003 UT (US) CN 1446540 A 10, 2003 (73) Assignee: LIPOCINE INC., Salt Lake City, UT (Continued) (US) OTHER PUBLICATIONS *) NotOt1Ce: Subjubject to anyy d1Sclaimer,disclai theh term off thisthi U.S. Appl. No. 14/801,737, filed Jul. 16, 2015; Chandrashekar patent is extended or adjusted under 35 Giliyar, Office Action dated Aug. 19, 2015. U.S.C. 154(b) by 26 days. (Continued) This patent is Subject to a terminal dis claimer. Primary Examiner — San-Ming Hui (21) Appl. No.: 14/261,057 (57) ABSTRACT (22) Filed: Apr. 24, 2014 The present invention provides for bioavailable oral dosage forms containingesters of 17-hydroxyprogesteroneas well as (65) Prior Publication Data related methods. The oral dosage forms can beformulated for pregnancy Support and can include atherapeutically effective US 2014/0271882 A1 Sep. -
Polymer Additives and Plasticizers
Polymer Additives and Plasticizers Library Listing – 1,799 spectra This library is a valuable addition to any polymer chemist’s toolbox. It includes spectra of plastics and additives for polymers, rubbers, cosmetics, adhesives, sealants, and plasticizers. The Polymers, Polymer Additives and Plasticizers Library features 1,799 spectra collected by Chemir/Polytech Laboratories and Dr. John Kokosa. Samples were run by transmission using one of the following techniques: molded film, capillary film or KBr disk. Each spectrum in the library includes information on manufacturer, chemical name, product name, chemical abstract number, and category name, where available. Chemically, the classes of polymer compounds represented in the library include: thermoplastics, thermoset resins, engineering polymers, monomers, and catalysts. Additives represented include: plasticizers, mold release agents, inorganic fillers, antistatic agents, surfactants, and colorants. Polymer Additives and Plasticizers Index Compound Name Index Compound Name 873 (2,2-THIOBIS-T-OCTYL- 533 1:1 LAUREL DEA PHENOLATO))-N-BUTYLAMINE 416 2,2',4,4'-TETRAHYDROXY NICKEL BENZOPHENONE 916 (2,4-DIHYDROXYPHENOL)- 1643 2,2'-(ETHYLHEXANAMIDE) METHANONE DIETHYL ETHYLHEXANOATE 917 (2-HYDROXY-4-(OCTYLOXY) 744 2,2'-ETHYLIDENE-BIS(4,6-DI-TERT- PHENYL) PHENYL-METHANONE BUTYLPHENOL) 1209 (2-HYDROXY-4-(OCTYLOXY) 733 2,2'-METHYLENE-BIS(4-METHYL-6- PHENYL) PHENYLMETHANONE NONYLPHENOL) 918 (2-HYDROXY-4- 714 2,2'-METHYLENE-BIS(4-METHYL-6- METHOXYPHENYL) PHENYL- TERTIARYBUTYL PHENOL) #1 METHANONE 712 -
Reaction Path Synthesis of Monoacylglycerol from Fat and Oils
Int. J. Pharm. Sci. Rev. Res., 35(1), November – December 2015; Article No. 23, Pages: 126-136 ISSN 0976 – 044X Review Article Reaction Path Synthesis of Monoacylglycerol from Fat and Oils Febri Odel Nitbania*, Juminaa, Dwi Siswantaa, Eti Nurwening Solikhahb aDepartment of Chemistry, Faculty of Mathematics and Natural Sciences, Gadjah Mada University, Sekip Utara, Yogyakarta, Indonesia. bPharmacology and Therapy, Medical Faculty, Gadjah Mada University, Sekip Utara, Yogyakarta, Indonesia. *Corresponding author’s E-mail: [email protected] Accepted on: 24-09-2015; Finalized on: 31-10-2015. ABSTRACT Monoacylglycerol is a typical of lipid compound, which plays a very significant role in food and cosmetic production as well as pharmaceutical industries. It is also categorised as a non-ionic surfactant as it contains a long hydrophobic acyl group and two hydrophilic hydroxyl groups. As a non-ionic surfactant, this compound plays a very essential role as an emulsifier in food industries and as an antimicrobial, antioxidant and anti-atherosclerotic in pharmaceutical industries. It is generally produced through a conventional process known as glycerolysis of oils or fats using inorganic alkaline catalyst at 220-260°C. Numerous approaches have been made to improve this reaction through several process including the enzymatic glycerolysis reaction of oils and fats, transesterification reaction of glycerol with fatty acid esters, alcoholysis reaction of oils and fats, esterification of free fatty acids and glycerol, transesterification reaction of fatty acid ester and esterification of free fatty acids with a protected glycerol compounds such as 1,2-O-isopropylidene glycerol and followed by its deprotection reaction using an acid resin such as Amberlyst-15.