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  1. Fulltext Enhancement of mechanical and thermal properties of oil palm empty fruit bunch fiber poly(butylene adipate-co-terephtalate) biocomposites by matrix esterification using succinic anhydride
    Siyamak S, Ibrahim NA, Abdolmohammadi S, Yunus WM, Rahman MZ
    Molecules, 2012 Feb 16;17(2):1969-91.
    PMID: 22343368 DOI: 10.3390/molecules17021969
    In this work, the oil palm empty fruit bunch (EFB) fiber was used as a source of lignocellulosic filler to fabricate a novel type of cost effective biodegradable composite, based on the aliphatic aromatic co-polyester poly(butylene adipate-co-terephtalate) PBAT (Ecoflex™), as a fully biodegradable thermoplastic polymer matrix. The aim of this research was to improve the new biocomposites' performance by chemical modification using succinic anhydride (SAH) as a coupling agent in the presence and absence of dicumyl peroxide (DCP) and benzoyl peroxide (BPO) as initiators. For the composite preparation, several blends were prepared with varying ratios of filler and matrix using the melt blending technique. The composites were prepared at various fiber contents of 10, 20, 30, 40 and 50 (wt %) and characterized. The effects of fiber loading and coupling agent loading on the thermal properties of biodegradable polymer composites were evaluated using thermal gravimetric analysis (TGA). Scanning Electron Microscopy (SEM) was used for morphological studies. The chemical structure of the new biocomposites was also analyzed using the Fourier Transform Infrared (FTIR) spectroscopy technique. The PBAT biocomposite reinforced with 40 (wt %) of EFB fiber showed the best mechanical properties compared to the other PBAT/EFB fiber biocomposites. Biocomposite treatment with 4 (wt %) succinic anhydride (SAH) and 1 (wt %) dicumyl peroxide (DCP) improved both tensile and flexural strength as well as tensile and flexural modulus. The FTIR analyses proved the mechanical test results by presenting the evidence of successful esterification using SAH/DCP in the biocomposites' spectra. The SEM micrograph of the tensile fractured surfaces showed the improvement of fiber-matrix adhesion after using SAH. The TGA results showed that chemical modification using SAH/DCP improved the thermal stability of the PBAT/EFB biocomposite.
    Matched MeSH terms: Esterification
  2. Fulltext Effect of fiber esterification on fundamental properties of oil palm empty fruit bunch fiber/poly(butylene adipate-co-terephthalate) biocomposites
    Siyamak S, Ibrahim NA, Abdolmohammadi S, Yunus WM, Rahman MZ
    Int J Mol Sci, 2012;13(2):1327-46.
    PMID: 22408394 DOI: 10.3390/ijms13021327
    A new class of biocomposites based on oil palm empty fruit bunch fiber and poly(butylene adipate-co-terephthalate) (PBAT), which is a biodegradable aliphatic aromatic co-polyester, were prepared using melt blending technique. The composites were prepared at various fiber contents of 10, 20, 30, 40 and 50 wt% and characterized. Chemical treatment of oil palm empty fruit bunch (EFB) fiber was successfully done by grafting succinic anhydride (SAH) onto the EFB fiber surface, and the modified fibers were obtained in two levels of grafting (low and high weight percentage gain, WPG) after 5 and 6 h of grafting. The FTIR characterization showed evidence of successful fiber esterification. The results showed that 40 wt% of fiber loading improved the tensile properties of the biocomposite. The effects of EFB fiber chemical treatments and various organic initiators content on mechanical and thermal properties and water absorption of PBAT/EFB 60/40 wt% biocomposites were also examined. The SAH-g-EFB fiber at low WPG in presence of 1 wt% of dicumyl peroxide (DCP) initiator was found to significantly enhance the tensile and flexural properties as well as water resistance of biocomposite (up to 24%) compared with those of untreated fiber reinforced composites. The thermal behavior of the composites was evaluated from thermogravimetric analysis (TGA)/differential thermogravimetric (DTG) thermograms. It was observed that, the chemical treatment has marginally improved the biocomposites' thermal stability in presence of 1 wt% of dicumyl peroxide at the low WPG level of grafting. The improved fiber-matrix surface enhancement in the chemically treated biocomposite was confirmed by SEM analysis of the tensile fractured specimens.
    Matched MeSH terms: Esterification
  3. Evaluating the Potential of Oleaginous Yeasts as Feedstock for Biodiesel Production
    Mukhtar H, Suliman SM, Shabbir A, Mumtaz MW, Rashid U, Rahimuddin SA
    Protein Pept Lett, 2018;25(2):195-201.
    PMID: 29359654 DOI: 10.2174/0929866525666180122112805
    BACKGROUND: Lipid-producing microorganisms, said to be oleaginous have been recognized since several years. We had investigated the effects of medium components and culturing situations on cell growth and lipid accumulation of oleaginous yeasts which were analytically examined so as to enhance lipid yield for biodiesel production.

    OBJECTIVE: The main objective of this study was to explore oleaginous yeast, Yarrowia lipolytica isolated from soil and optimization of culture conditions and medium components to obtained better quality microbial oil for biodiesel production.

    METHODS: Fifty yeast strains were isolated from soil from different regions of Lahore and eleven of them were selected for oil production. The isolated yeast colonies were screened to further check their lipid producing capabilities by the qualitative analysis. Five yeast strains were designated as oleaginous because they produced more than 16% of oil based on their biomass. To estimate the total lipid content of yeast cells, the extraction of lipids was done by performing the procedure proposed by Bligh and Dyer. The transesterification of yeast oils was performed by using different methods. There were three different strategies customized to transesterifying microbial oil using base catalyzed transesterification, acid catalyzed transesterification and enzyme-based transesterification. After completion of transesterification, sample was used for fatty acid methyl esters (FAMEs) were analyzed by gas-chromatograph with ionization detector type MS.

    RESULTS: The isolate IIB-10 identified as Yarrowia lipolytica produced maximum amount of lipids i.e. 22.8%. More amount of biomass was obtained when cane molasses was utilized as carbon source where it produced 29.4 g/L of biomass while sucrose and lactose were not utilized by IIB-10 and no biomass was obtained. Similarly, meat extracts showed best results when it was used as nitrogen source because it resulted in 35.8 g/L biomass of Yarrowia lipolytica IIB-10. The culturing conditions like size of inoculum, effect of pH and time of incubation were also studied. The 10% of inoculum size produced 25.4 g/L biomass at 120 h incubation time, while the pH 7 was the optimum pH at which 24.8 g/L biomass was produced by Yarrowia lipolytica IIB-10. GC-MS analysis showed that biodiesel produced by transesterification contained similar fatty acids as found in vegetable oil for this reason it is widely accepted feedstock for biodiesel production.

    CONCLUSION: The analysis of fatty acids methyl esters showed the similar composition of microbial oil as in vegetable oils and high amount of methyl esters were obtained after transesterification. Therefore, potentially oleaginous yeast could be used to generate a large amount of lipids for biodiesel production that will be the better substitute of petroleum-based diesel and will also control the environmental pollution.

    Matched MeSH terms: Esterification
  4. Technical difficulties and solutions of direct transesterification process of microbial oil for biodiesel synthesis
    Yousuf A, Khan MR, Islam MA, Wahid ZA, Pirozzi D
    Biotechnol Lett, 2017 Jan;39(1):13-23.
    PMID: 27659031 DOI: 10.1007/s10529-016-2217-x
    Microbial oils are considered as alternative to vegetable oils or animal fats as biodiesel feedstock. Microalgae and oleaginous yeast are the main candidates of microbial oil producers' community. However, biodiesel synthesis from these sources is associated with high cost and process complexity. The traditional transesterification method includes several steps such as biomass drying, cell disruption, oil extraction and solvent recovery. Therefore, direct transesterification or in situ transesterification, which combines all the steps in a single reactor, has been suggested to make the process cost effective. Nevertheless, the process is not applicable for large-scale biodiesel production having some difficulties such as high water content of biomass that makes the reaction rate slower and hurdles of cell disruption makes the efficiency of oil extraction lower. Additionally, it requires high heating energy in the solvent extraction and recovery stage. To resolve these difficulties, this review suggests the application of antimicrobial peptides and high electric fields to foster the microbial cell wall disruption.
    Matched MeSH terms: Esterification/physiology
  5. Fulltext One-Step Partially Purified Lipases (ScLipA and ScLipB) from Schizophyllum commune UTARA1 Obtained via Solid State Fermentation and Their Applications
    Kam YC, Woo KK, Ong LGA
    Molecules, 2017 Dec 08;22(12).
    PMID: 29292721 DOI: 10.3390/molecules22122106
    Lipases with unique characteristics are of value in industrial applications, especially those targeting cost-effectiveness and less downstream processes. The aims of this research were to: (i) optimize the fermentation parameters via solid state fermentation (SSF); and (ii) study the performance in hydrolysis and esterification processes of the one-step partially purified Schizophyllum commune UTARA1 lipases. Lipase was produced by cultivating S. commune UTARA1 on sugarcane bagasse (SB) with used cooking oil (UCO) via SSF and its production was optimized using Design-Expert® 7.0.0. Fractions 30% (ScLipA) and 70% (ScLipB) which contained high lipase activity were obtained by stepwise (NH₄)₂SO₄ precipitation. Crude fish oil, coconut oil and butter were used to investigate the lipase hydrolysis capabilities by a free glycerol assay. Results showed that ScLipA has affinities for long, medium and short chain triglycerides, as all the oils investigated were degraded, whereas ScLipB has affinities for long chain triglycerides as it only degrades crude fish oil. During esterification, ScLipA was able to synthesize trilaurin and triacetin. Conversely, ScLipB was specific towards the formation of 2-mono-olein and triacetin. From the results obtained, it was determined that ScLipA and ScLipB are sn-2 regioselective lipases. Hence, the one-step partial purification strategy proved to be feasible for partial purification of S. commune UTARA1 lipases that has potential use in industrial applications.
    Matched MeSH terms: Esterification
  6. Effects of chemical interesterification on the physicochemical, microstructural and thermal properties of palm stearin, palm kernel oil and soybean oil blends
    Fauzi SH, Rashid NA, Omar Z
    Food Chem, 2013 Apr 15;137(1-4):8-17.
    PMID: 23199984 DOI: 10.1016/j.foodchem.2012.09.086
    Blends of palm stearin (PS), palm kernel oil (PKO) and soybean oil (SBO) at certain proportions were formulated using a mixture design based on simplex-lattice (Design Expert 8.0.4 Stat-Ease Inc., Minneapolis, 2010). All the 10 oil blends were subjected to chemical interesterification (CIE) using sodium methoxide as the catalyst. The solid fat content (SFC), triacylglycerol (TAG) composition, thermal properties (DSC), polymorphism and microstructural properties were studied. Palm-based trans-free table margarine containing ternary mixture of PS/PKO/SBO [49/20/31 (w/w)], was optimally formulated through analysis of multiple isosolid diagrams and was found to have quite similar SMP and SFC profile as compared to the commercial table margarine. This study has shown chemical interesterification are effective in modifying the physicochemical properties of palm stearin, palm kernel oil, soybean oil and their mixtures.
    Matched MeSH terms: Esterification
  7. Esterification of levulinic acid to levulinate esters in the presence of sulfated silica catalyst
    Nur Aainaa Syahirah Ramli, Nur Irsalina Hisham, Nor Aishah Saidina Amin
    Sains Malaysiana, 2018;47:1131-1138.
    Levulinic acid (LA) is one of biomass derived building block chemicals with various applications. Catalytic esterification
    of LA with alkyl alcohol produces levulinate ester which can be applied as fragrance, flavouring agents, as well as fuel
    additives. In this study, a series of sulfated silica (SiO2
    ) catalyst was prepared by modification of SiO2
    with sulfuric acid
    (H2
    SO4
    ) at different concentrations; 0.5 M to 5 M H2
    SO4
    . The catalysts were characterized, and tested for esterification
    of LA with ethanol to ethyl levulinate (EL). The effect of various reaction parameters including reaction time, catalyst
    loading and molar ratio of LA to ethanol on esterification of LA to EL were inspected. The catalyst with high concentration
    of acid sites seemed suitable for LA esterification to EL. Among the sulfated SiO2
    catalysts tested (0.5 M-SiO2
    , 1 M-SiO2
    ,
    3 M-SiO2
    and 5 M-SiO2
    ), 3 M-SiO2
    exhibited the highest performance with the optimum EL yield of 54% for reaction
    conducted at reflux temperature for 4 h, 30% 3 M-SiO2
    loading and LA to ethanol molar ratio of 1:20. Besides, the
    reusability of 3 M-SiO2
    catalyst for LA esterification with ethanol was examined for five cycles. Esterification of LA with
    methanol and 1-butanol were also carried out for methyl levulinate (ML) and butyl levulinate (BL) productions with 69%
    and 40% of ML and BL yields, respectively. This study demonstrates the potential of sulfated SiO2
    catalyst for levulinate
    ester production from LA at mild process condition.
    Matched MeSH terms: Esterification
  8. Fulltext Topical piroxicam in vitro release and in vivo anti-inflammatory and analgesic effects from palm oil esters-based nanocream
    Abdulkarim MF, Abdullah GZ, Chitneni M, Salman IM, Ameer OZ, Yam MF, et al.
    Int J Nanomedicine, 2010 Nov 04;5:915-24.
    PMID: 21116332 DOI: 10.2147/IJN.S13305
    INTRODUCTION: During recent years, there has been growing interest in use of topical vehicle systems to assist in drug permeation through the skin. Drugs of interest are usually those that are problematic when given orally, such as piroxicam, a highly effective anti-inflammatory, anti-pyretic, and analgesic, but with the adverse effect of causing gastrointestinal ulcers. The present study investigated the in vitro and in vivo pharmacodynamic activity of a newly synthesized palm oil esters (POEs)-based nanocream containing piroxicam for topical delivery.

    METHODS: A ratio of 25:37:38 of POEs: external phase: surfactants (Tween 80:Span 20, in a ratio 80:20), respectively was selected as the basic composition for the production of a nanocream with ideal properties. Various nanocreams were prepared using phosphate-buffered saline as the external phase at three different pH values. The abilities of these formulae to deliver piroxicam were assessed in vitro using a Franz diffusion cell fitted with a cellulose acetate membrane and full thickness rat skin. These formulae were also evaluated in vivo by comparing their anti-inflammatory and analgesic activities with those of the currently marketed gel.

    RESULTS: After eight hours, nearly 100% of drug was transferred through the artificial membrane from the prepared formula F3 (phosphate-buffered saline at pH 7.4 as the external phase) and the marketed gel. The steady-state flux through rat skin of all formulae tested was higher than that of the marketed gel. Pharmacodynamically, nanocream formula F3 exhibited the highest anti- inflammatory and analgesic effects as compared with the other formulae.

    CONCLUSION: The nanocream containing the newly synthesized POEs was successful for trans-dermal delivery of piroxicam.

    Matched MeSH terms: Esterification
  9. Complete fatty acid analysis data of flaxseed oil using GC-FID method
    Danish M, Nizami M
    Data Brief, 2019 Apr;23:103845.
    PMID: 31372470 DOI: 10.1016/j.dib.2019.103845
    The data presented in this article were generated through the gas chromatography (GC) with a flame ionization detector (FID). The flaxseed oil was converted into fatty acid methyl ester (FAME) then used in the GC with FID and observe the retention time of different fatty acid present in the flaxseed oil. The observed retention time was compared with the standard fatty acid to confirm the specific fatty acid presence in the flaxseed oil. The part of the data is used in the article "Optimization of the process variable for biodiesel production by transesterification of flaxseed oil and produced biodiesel characterizations" Renewable Energy journal (Ahmad et al., 2019).
    Matched MeSH terms: Esterification
  10. Synthesis of oil palm empty fruit bunch (EFB) derived solid acid catalyst for esterification of waste cooking oils
    Koguleshun S, Pua FL, Shamala G, Nabihah S
    Sains Malaysiana, 2015;44:1573-1577.
    Oil palm empty fruit bunch (EFB) contributes to a large quantity of lignocellulosic waste. It is an abundantly available
    waste biomass in Malaysia. This project was aimed to utilize the waste materials for a better benefit. EFB were used as
    raw material to prepare a new solid catalyst for biodiesel production. Solid acid catalyst derived from EFB was used to
    catalyze the esterification process in biodiesel production from waste cooking oil. Solid acid catalyst was prepared by
    direct impregnation with transition metal sulfides, Fe2
    (SO4
    )3
    . This new catalyst was used to catalyze the esterification of
    high free fatty acid (FFA) value oil, e.g. waste cooking oils (WCOs) as pre-treatment step prior to biodiesel production.
    The highest catalytic activity with 90.95% esterification rate was achieved. The catalyst can be easily separated for
    reuse compared to homogenous catalyst which are used in biodiesel production. EFB has the potential to be converted
    into useful feedstock and the derived catalyst can replace the traditional liquid acid catalyst in biodiesel production
    especially for high acid value content feedstock.
    Matched MeSH terms: Esterification
  11. A mini scale batch reactor for the production of palm‑based polyol
    Khairiah Haji Badri, Muhammad Syukri Ngah
    Sains Malaysiana, 2015;44:861-867.
    An investigation on a batch production of palm kernel oil polyol (PKO-p) was conducted via esterification and condensation.
    The process design was thoroughly studied as a preliminary step for future upscaling. The process variables included
    necessity of vacuum pump, controlling of heating rate, recording the production time, nitrogen gas flow and agitator
    speed. About 250 mL PKO-p was successfully synthesized within 3 h. Vacuum pressure was applied to haul out moisture
    from the system. The control of heating rate and production time are vital to avoid sudden oxidation.
    Matched MeSH terms: Esterification
  12. Fulltext Functional and preliminary characterisation of hydrocolloid from tamarillo (Solanum betaceum Cav.) puree
    Gannasin SP, Ramakrishnan Y, Adzahan NM, Muhammad K
    Molecules, 2012 Jun 05;17(6):6869-85.
    PMID: 22669042 DOI: 10.3390/molecules17066869
    Hydrocolloid from tamarillo (Solanum betaceum Cav.) puree was extracted using water and characterised for the first time. Proximate compositions of the extracted hydrocolloid were also determined. Functional characteristics such as water-holding capacity, oil-holding capacity, emulsifying activity, emulsion stability, foaming capacity and stability of the hydrocolloid were evaluated in comparison to that of commercial hydrocolloids. Its functional groups and degree of esterification were determined using Fourier Transform Infrared (FT-IR) spectroscopy. Monosaccharide profiling was done using reverse-phase high pressure liquid chromatography (RP-HPLC). Screening of various fruits for high hydrocolloid yield after water extraction resulted in tamarillo giving the highest yield. The yield on dry weight basis was 8.30%. The hydrocolloid constituted of 0.83% starch, 21.18% protein and 66.48% dietary fibre with 49.47% degree of esterification and the monosaccharides identified were mannose, ribose, rhamnose, galacturonic acid, glucose, galactose, xylose and arabinose. Higher oil-holding capacity, emulsifying activity and emulsion stability compared to commercial hydrocolloids propose its possible application as a food emulsifier and bile acid binder. Foaming capacity of 32.19% and good foam stabilisation (79.36% of initial foam volume after 2 h of foam formation) suggest its promising application in frothy beverages and other foam based food products. These findings suggest that water-extracted tamarillo hydrocolloid can be utilised as an alternative to low methoxyl pectin.
    Matched MeSH terms: Esterification
  13. Kinetic study on microwave-assisted esterification of free fatty acids derived from Ceiba pentandra Seed Oil
    Lieu T, Yusup S, Moniruzzaman M
    Bioresour Technol, 2016 Jul;211:248-56.
    PMID: 27019128 DOI: 10.1016/j.biortech.2016.03.105
    Recently, a great attention has been paid to advanced microwave technology that can be used to markedly enhance the biodiesel production process. Ceiba pentandra Seed Oil containing high free fatty acids (FFA) was utilized as a non-edible feedstock for biodiesel production. Microwave-assisted esterification pretreatment was conducted to reduce the FFA content for promoting a high-quality product in the next step. At optimum condition, the conversion was achieved 94.43% using 2wt% of sulfuric acid as catalyst where as 20.83% conversion was attained without catalyst. The kinetics of this esterification reaction was also studied to determine the influence of factors on the rate of reaction and reaction mechanisms. The results indicated that microwave-assisted esterification was of endothermic second-order reaction with the activation energy of 53.717kJ/mol.
    Matched MeSH terms: Esterification
  14. Optimization of Pectin Extraction from Sweet Potato Peels Using Citric Acid and its Emulsifying Properties
    Hamidon NH, Abang Zaidel DN, Mohd Jusoh YM
    Recent Pat Food Nutr Agric, 2020;11(3):202-210.
    PMID: 32031081 DOI: 10.2174/2212798411666200207102051
    BACKGROUND: Pectin is a natural polysaccharide that has been used widely as a stabilizer in food emulsion system.

    OBJECTIVE: This study aimed to optimize the yield of pectin extracted from sweet potato residue and investigate its emulsifying properties.

    METHODS: Response surface methodology (RSM) has been utilized to investigate the pectin extracted from sweet potato peels using citric acid as the extracting solvent. Investigation of the effect of different extraction conditions namely temperature (°C), time (min) and solution pH on pectin yield (%) were conducted. A Box-Benhken design with three levels of variation was used to optimize the extraction conditions.

    RESULTS: The optimal conditions determined were temperature 76°C, time 64 min and pH 1.2 with 65.2% yield of pectin. The degree of esterification (DE) of the sweet potato pectin was determined using Fourier Transform Infrared (FTIR) Spectroscopy. The pectin is high-methoxyl pectin with DE of 58.5%. Emulsifying properties of sweet potato pectin were investigated by measuring the zeta-potential, particle size and creaming index with addition of 0.4 and 1.0 wt % pectin to the emulsion.

    CONCLUSION: Extraction using citric acid could improve the pectin yield. Improved emulsion stability was observed with the addition of the sweet potato pectin.

    Matched MeSH terms: Esterification
  15. Homogeneous, heterogeneous and enzymatic catalysis for transesterification of high free fatty acid oil (waste cooking oil) to biodiesel: a review
    Lam MK, Lee KT, Mohamed AR
    Biotechnol Adv, 2010 Jul-Aug;28(4):500-18.
    PMID: 20362044 DOI: 10.1016/j.biotechadv.2010.03.002
    In the last few years, biodiesel has emerged as one of the most potential renewable energy to replace current petrol-derived diesel. It is a renewable, biodegradable and non-toxic fuel which can be easily produced through transesterification reaction. However, current commercial usage of refined vegetable oils for biodiesel production is impractical and uneconomical due to high feedstock cost and priority as food resources. Low-grade oil, typically waste cooking oil can be a better alternative; however, the high free fatty acids (FFA) content in waste cooking oil has become the main drawback for this potential feedstock. Therefore, this review paper is aimed to give an overview on the current status of biodiesel production and the potential of waste cooking oil as an alternative feedstock. Advantages and limitations of using homogeneous, heterogeneous and enzymatic transesterification on oil with high FFA (mostly waste cooking oil) are discussed in detail. It was found that using heterogeneous acid catalyst and enzyme are the best option to produce biodiesel from oil with high FFA as compared to the current commercial homogeneous base-catalyzed process. However, these heterogeneous acid and enzyme catalyze system still suffers from serious mass transfer limitation problems and therefore are not favorable for industrial application. Nevertheless, towards the end of this review paper, a few latest technological developments that have the potential to overcome the mass transfer limitation problem such as oscillatory flow reactor (OFR), ultrasonication, microwave reactor and co-solvent are reviewed. With proper research focus and development, waste cooking oil can indeed become the next ideal feedstock for biodiesel.
    Matched MeSH terms: Esterification
  16. A glycerol-free process to produce biodiesel by supercritical methyl acetate technology: an optimization study via Response Surface Methodology
    Tan KT, Lee KT, Mohamed AR
    Bioresour Technol, 2010 Feb;101(3):965-9.
    PMID: 19773156 DOI: 10.1016/j.biortech.2009.09.004
    In this study, fatty acid methyl esters (FAME) have been successfully produced from transesterification reaction between triglycerides and methyl acetate, instead of alcohol. In this non-catalytic supercritical methyl acetate (SCMA) technology, triacetin which is a valuable biodiesel additive is produced as side product rather than glycerol, which has lower commercial value. Besides, the properties of the biodiesel (FAME and triacetin) were found to be superior compared to those produced from conventional catalytic reactions (FAME only). In this study, the effects of various important parameters on the yield of biodiesel were optimized by utilizing Response Surface Methodology (RSM) analysis. The mathematical model developed was found to be adequate and statistically accurate to predict the optimum yield of biodiesel. The optimum conditions were found to be 399 degrees C for reaction temperature, 30 mol/mol of methyl acetate to oil molar ratio and reaction time of 59 min to achieve 97.6% biodiesel yield.
    Matched MeSH terms: Esterification*
  17. Fulltext An Improved Nanoemulsion Formulation Containing Kojic Monooleate: Optimization, Characterization and In Vitro Studies
    Roselan MA, Ashari SE, Faujan NH, Mohd Faudzi SM, Mohamad R
    Molecules, 2020 Jun 04;25(11).
    PMID: 32512808 DOI: 10.3390/molecules25112616
    Tyrosinase inhibitors have become increasingly important targets for hyperpigmentation disease treatment. Kojic monooleate (KMO), synthesized from the esterification of kojic acid and oleic acid, has shown a better depigmenting effect than kojic acid. In this study, the process parameters include the speed of high shear, the time of high shear and the speed of the stirrer in the production of nanoemulsion containing KMO was optimized using Response Surface Methodology (RSM), as well as evaluated in terms of its physicochemical properties, safety and efficacy. The optimized condition for the formulation of KMO nanoemulsion was 8.04 min (time of high shear), 4905.42 rpm (speed of high shear), and 271.77 rpm (speed of stirrer), which resulted in a droplet size of 103.97 nm. An analysis of variance (ANOVA) showed that the fitness of the quadratic polynomial fit the experimental data with large F-values (148.79) and small p-values (p < 0.0001) and an insignificant lack of fit. The optimized nanoemulsion containing KMO with a pH value of 5.75, showed a high conductivity value (3.98 mS/cm), which indicated that the nanoemulsion containing KMO was identified as an oil-in-water type of nanoemulsion. The nanoemulsion remains stable (no phase separation) under a centrifugation test and displays accelerated stability during storage at 4, 25 and 45 °C over 90 days. The cytotoxicity assay showed that the optimized nanoemulsion was less toxic, with a 50% inhibition of cell viability (IC50) > 500 μg/mL, and that it can inhibit 67.12% of tyrosinase activity. This study reveals that KMO is a promising candidate for the development of a safe cosmetic agent to prevent hyperpigmentation.
    Matched MeSH terms: Esterification
  18. One-pot lipase-catalyzed esterification of ε-caprolactone with methyl-d-glucopyranoside and its elongation with free 6-hydroxyhexanoate monomer units
    Saat MN, Mohamad Annuar MS
    Biotechnol Appl Biochem, 2020 May;67(3):354-365.
    PMID: 31746015 DOI: 10.1002/bab.1859
    One-pot synthesis of sugar-functionalized oligomeric caprolactone was carried out by lipase-catalyzed esterification of ε-caprolactone (ECL) with methyl-d-glucopyranoside (MGP) followed by the elongation of functionalized oligomer chain. Functionalization was performed in a custom-fabricated glass reactor equipped with Rushton turbine impeller and controlled temperature at 60 °C using tert-butanol as reaction medium. The overall reaction steps include MGP esterification of ECL monomer and its subsequent elongation by free 6-hydroxyhexanoate monomer units. A ping-pong bi-bi mechanism without ternary complex was proposed for esterification of ECL and MGP with apparent values of kinetic constant, namely maximal velocity (Vmax ), Michaelis constant for MGP (KmMGP ), and Michaelis constant for ECL (KmECL ) at 3.848 × 10-3  M H-1 , 8.189 × 10-2  M, and 6.050 M, respectively. Chain propagation step of MGP-functionalized ECL oligomer exhibits the properties of living polymerization mechanism. Linear relationship between conversion (%) and number average molecular weight, Mn (g mol-1 ), of functionalized oligomer was observed. Synthesized functionalized oligomer showed narrow range of molecular weight from 1,400 to 1,600 g mol-1 with more than 90% conversion achieved. Structural analysis confirmed the presence of covalent bond between the hydroxyl group in MGP with carboxyl end group of ECL oligomer.
    Matched MeSH terms: Esterification
  19. Fulltext The Role of Solvent-Accessible Leu-208 of Cold-Active Pseudomonas fluorescens Strain AMS8 Lipase in Interfacial Activation, Substrate Accessibility and Low-Molecular Weight Esterification in the Presence of Toluene
    Yaacob N, Ahmad Kamarudin NH, Leow ATC, Salleh AB, Raja Abd Rahman RNZ, Mohamad Ali MS
    Molecules, 2017 Aug 12;22(8).
    PMID: 28805665 DOI: 10.3390/molecules22081312
    The alkaline cold-active lipase from Pseudomonas fluorescens AMS8 undergoes major structural changes when reacted with hydrophobic organic solvents. In toluene, the AMS8 lipase catalytic region is exposed by the moving hydrophobic lid 2 (Glu-148 to Gly-167). Solvent-accessible surface area analysis revealed that Leu-208, which is located next to the nucleophilic Ser-207 has a focal function in influencing substrate accessibility and flexibility of the catalytic pocket. Based on molecular dynamic simulations, it was found that Leu-208 strongly facilitates the lid 2 opening via its side-chain. The KM and Kcat/KM of L208A mutant were substrate dependent as it preferred a smaller-chain ester (pNP-caprylate) as compared to medium (pNP-laurate) or long-chain (pNP-palmitate) esters. In esterification of ethyl hexanoate, L208A promotes a higher ester conversion rate at 20 °C but not at 30 °C, as a 27% decline was observed. Interestingly, the wild-type (WT) lipase's conversion rate was found to increase with a higher temperature. WT lipase AMS8 esterification was higher in toluene as compared to L208A. Hence, the results showed that Leu-208 of AMS8 lipase plays an important role in steering a broad range of substrates into its active site region by regulating the flexibility of this region. Leu-208 is therefore predicted to be crucial for its role in interfacial activation and catalysis in toluene.
    Matched MeSH terms: Esterification
  20. Interesterification of engkabang (Shorea macrophylla) fat--canola oil blend with lipase from Candida antarctica to simulate the properties of lard
    Illiyin MR, Marikkar JM, Loke MK, Shuhaimi M, Mahiran B, Miskandar MS
    J Oleo Sci, 2014;63(1):39-46.
    PMID: 24389796
    A study was carried out to compare the composition and thermal properties of lard (LD) and engkabang fat (EF) - canola oil (CaO) blend interesterified with Candida antartica lipase (C. antartica). A fat blend EF-4 (40% EF in CaO) was prepared and interesterified using C. antartica lipase at 60°C for different time intervals (6 h, 12 h and 24 h) with 200 rpm agitation. The fat blends before and after interesterification were compared to LD with respect to their slip melting points (SMP), fatty acid and triacyglycerol (TAG) compositions, melting, solidification and polymorphic properties. Result showed that the slip melting point (SMP) of the fat blend interesterified for 6 h was the closest to that of LD. The solid fat content (SFC) values of fat blends interesterified for 12 and 24 h were found to become equal to those of LD within the temperature range of 0 to 20°C. In addition, all three interesterified blends had SFC values similar to those of LD within the temperature range of 30-40°C. According to thermal analysis, the transition of the fat blend interesterified for 24 h appearing at -2.39°C was similar to the low melting thermal transition of LD and the transition of the fat blend interesterified for 12 h appearing at 26.25°C was similar to the high melting thermal transition of LD. However, there is no compatibility between LD and all three interesterified blends with regard to polymorphic behaviour.
    Matched MeSH terms: Esterification
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