Trilaurin

Manufactured by Merck Group

Sourced in United States, United Kingdom

Trilaurin is a lipid-based excipient used in the formulation of pharmaceutical and cosmetic products. It is a solid, waxy compound composed of three lauric acid molecules esterified with glycerol. Trilaurin serves as a lubricant, binder, and emollient in various applications, but its specific intended uses should not be extrapolated.

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Lab products found in correlation

Sepharose cl 4b, by Merck Group (4 mentions) Epikuron 200, by Cargill (4 mentions) Tripalmitin, by Merck Group (3 mentions) Tricaprin, by Merck Group (3 mentions) Myristic acid, by Merck Group (3 mentions) Stearic acid, by Merck Group (3 mentions) Trimyristin, by Merck Group (3 mentions) Sodium hydroxide (naoh), by Merck Group (3 mentions) Fetal bovine serum (fbs), by Thermo Fisher Scientific (3 mentions) Triolein, by Merck Group (2 mentions) Sodium chloride (nacl), by Thermo Fisher Scientific (2 mentions) Phosphoric acid, by Thermo Fisher Scientific (2 mentions) Calcium chloride, by Merck Group (2 mentions) Sodium phosphate dibasic dihydrate, by Merck Group (2 mentions) Ethyl acetate, by Merck Group (2 mentions) Pluronic f68, by Merck Group (2 mentions) 1 2 propanediol, by Merck Group (2 mentions) Cremophor rh60, by BASF (2 mentions) Tristearin, by Merck Group (2 mentions) Penicillin streptomycin, by Thermo Fisher Scientific (2 mentions)

13 protocols using trilaurin

Isolation and Characterization of Chestnut Lipase

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Korean chestnuts (Castanea crenata) were purchased from local markets. They were peeled, sealed in a vacuum plastic bag, and stored at 4 °C for subsequent use. Before use, the chestnuts were covered with a layer of wet cotton and allowed to germinate for 3 days at 18 °C.
HiTrap DEAE Sepharose Fast Flow, HiTrap Q Sepharose Fast Flow, and HiPrep Sephacryl S-100 HR were purchased from Cytiva (Uppsala, Sweden). Trizma® base (≥ 99.9%), diethyl ether (≥ 99.9%), p-nitrophenyl palmitate (p-NPP), sodium dodecyl sulfate (SDS), isooctane (IOT), tributyrin, tricaproin, tricaprin, trilaurin, tripalmitin, and triolein (≥ 99.0%) were purchased from Sigma-Aldrich Co. (St. Louis, MO, USA). Ammonium sulfate (≥ 99.5%), Triton X-100, sodium chloride (≥ 99.5%), and agar were purchased from Junsei Chemical Co., Ltd. (Tokyo, Japan). Boric acid, potassium chloride, and oleic acid were obtained from Duksan Pure Chemicals Co., Ltd. (Ansan, Gyeonggi-do, Korea). The Costar® 96-well microplates (clear wall, clear bottom) used for the fluorometric assay were purchased from Corning Co. (Corning, NY, USA). All other chemicals were of analytical grade and were used without further purification.

Heo J., Kwon C.W., Lee J., Park H., Yu H, & Chang P.S. (2022). A jacalin-related lectin domain-containing lipase from chestnut (Castanea crenata): Purification, characterization, and protein identification. Current Research in Food Science, 5, 2081-2093.

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Comprehensive Solvent and Standard Sourcing

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All solvents of LC–MS grade or better were ordered from Sigma Aldrich (Gillingham, UK). All internal standards were obtained from Avanti Polar Lipids (through Instruchem, Delfzijn, NL) with the exception of undecanoic acid and trilaurin (Sigma Aldrich, Gillingham, UK).

Koulman A., Prentice P., Wong M.C., Matthews L., Bond N.J., Eiden M., Griffin J.L, & Dunger D.B. (2014). The development and validation of a fast and robust dried blood spot based lipid profiling method to study infant metabolism. Metabolomics, 10(5), 1018-1025.

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Liposomal Formulation Development

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Trilaurin, benzyl alcohol, ethyl acetate, propylene glycol, Sudan Red III (1-[4-(phenylazo)phenylazo]-2-naphthol), sodium hydroxide, calcium chloride, sodium phosphate dibasic dihydrate, myristic acid, stearic acid, behenic acid, taurocholic acid sodium salt (TC), stearylamine, Sepharose^®CL4B were obtained from Sigma Aldrich (St. Louis, MO, USA). Epikuron^®200 (soybean lecithin, containing 95% phosphatidylcholine) was obtaine from Cargill (Minneapolis, MN, USA); Cremophor^®RH60 (PEG-60 hydrogenated castor oil) was from Acef (Piacenza, Italy); sodium chloride and phosphoric acid were from Alfa Aesar (Haverhill, MA, USA).

Sapino S., Chindamo G., Chirio D., Manzoli M., Peira E., Riganti C, & Gallarate M. (2021). Calcium Phosphate-Coated Lipid Nanoparticles as a Potential Tool in Bone Diseases Therapy. Nanomaterials, 11(11), 2983.

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Trilaurin-based Nanoparticle Formulation Development

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Trilaurin (purity ≥ 99%), ethyl acetate (EA, purity ≥ 99.5%), propylene glycol (purity ≥ 99.5%), sodium hydroxide (purity ≥ 98%), calcium chloride (purity ≥ 96%), sodium phosphate dibasic dihydrate (purity ≥ 99%), and Sepharose^® CL4B were from Sigma Aldrich (St. Louis, MO, USA). Epikuron^®200 (soybean lecithin, containing 95% phosphatidylcholine) was from Cargill (Minneapolis, MN, USA); Cremophor^®RH60 (PEG-60 hydrogenated castor oil) was from Acef (Piacenza, Italy); sodium chloride (purity ≥ 99%) and phosphoric acid (≥85% w/w in H₂O) were from Alfa Aesar (Haverhill, MA, USA).

Chirio D., Sapino S., Chindamo G., Peira E., Vercelli C., Riganti C., Manzoli M., Gambino G., Re G, & Gallarate M. (2022). Doxorubicin-Loaded Lipid Nanoparticles Coated with Calcium Phosphate as a Potential Tool in Human and Canine Osteosarcoma Therapy. Pharmaceutics, 14(7), 1362.

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Formulation and Characterization of Doxorubicin Nanocarriers

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Trilaurin (TL), ethyl acetate (EA), benzyl alcohol (BenzOH), butyl lactate (BL), sodium taurocholate (NaTC), Pluronic^® F68, 1,2 propanediol, CURC, cholesterol, chitosan and Sepharose^® CL 4B, doxorubicin were purchased from Sigma Chemicals Co. (St. Louis, MO, USA). Epikuron^®200 (lecithin-phosphatydilcoline 92%) was from Cargill (Minneapolis, MN, USA), Cremophor^®RH 60 (PEG-60 hydrogenated castor oil) from BASF (Ludwigshafen, Germany). The plastic ware for cell cultures was obtained from Falcon (Becton Dickinson, Franklin Lakes, NJ, USA). The electrophoresis reagents were from Bio-Rad Laboratories (Hercules, CA, USA). The protein content of cell lysates was assessed with the BCA kit from Sigma Chemicals Co. Deionized water was obtained by a MilliQ system (Millipore, St. Louis, MO, USA). Unless specified otherwise, all reagents were purchased from Sigma Chemicals Co.

Fathy Abd-Ellatef G.E., Gazzano E., Chirio D., Ragab Hamed A., Belisario D.C., Zuddas C., Peira E., Rolando B., Kopecka J., Assem Said Marie M., Sapino S., Ramadan Fahmy S., Gallarate M., Zaki Abdel-Hamid A.H, & Riganti C. (2020). Curcumin-Loaded Solid Lipid Nanoparticles Bypass P-Glycoprotein Mediated Doxorubicin Resistance in Triple Negative Breast Cancer Cells. Pharmaceutics, 12(2), 96.

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Nanoparticle Formulation Development

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Trilaurin (TL), tristearin, myristic acid, glyceryl monostearate, ethyl acetate (EA), benzyl alcohol (BenzOH), triacetin (TA), butyl lactate (BL), polysorbate (20, 40, 80), sodium taurodeoxycholate (Na TdC), sodium taurocholate (Na TC), sodium glycocholate (Na GC), sodium cholate (Na C), Pluronic^® F68, polyvinyl alcohol (PVA) 9000, PVA 14000, 1,2 propanediol, curcumin and Sepharose^® CL 4B were purchased from Sigma (Dorset, UK). Trimyristin was from Alfa Aesar (Karlsruhe, Germany), glyceryl dibehenate was from Gattefossé (Weil am Rhein, Germany), Epikuron^® 200 (lecithin-phosphatydil coline 92%) from Cargill (Minneapolis, MN, USA), and Cremophor^® RH 60 (PEG-60 hydrogenated castor oil) from BASF (Ludwigshafen, Germany).

Chirio D., Peira E., Dianzani C., Muntoni E., Gigliotti C.L., Ferrara B., Sapino S., Chindamo G, & Gallarate M. (2019). Development of Solid Lipid Nanoparticles by Cold Dilution of Microemulsions: Curcumin Loading, Preliminary In Vitro Studies, and Biodistribution. Nanomaterials, 9(2), 230.

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Multifunctional Nanoparticle Delivery System

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Trilaurin, sodium laurate, monomethoxy-polyethylene glycols (mPEG), cholesteryl Chloroformate, N-hydroxysuccinimide, N,N′-dicyclohexylcarbodiimide (DCC), cysteamine, verapamil, β-estradiol, 3,3′-dioctadecyloxacarbocyanine perchlorate (DiO), Hoechst 33258, and rhodamine B were obtained from Sigma-Aldrich (St Louis, MO, USA, and Seelze, Germany). DOX and ω-maleimide-polyethylene glycol-amine were purchased from Seedchem (Melbourne, Australia) and Jenkem (Beijing, People’s Republic of China), respectively. DSPE-PEG was obtained from Avanti Polar Lipids (Alabaster, AL, USA). Chloroform, dimethyl sulfoxide (DMSO), and paraformaldehyde (PFA) were obtained from TEDIA (Fairfield, OH, USA). All organic reagents were of analytical grade. For cell culture studies, Dulbecco’s Modified Eagle’s Medium (DMEM), fetal bovine serum (FBS), and 0.25% trypsin–EDTA and penicillin–streptomycin solutions were purchased from Thermo Fisher Scientific (Waltham, MA, USA). Alamar Blue, a cell viability reagent, was purchased from Thermo Fisher Scientific. MCF-7 and MCF-7/MDR were obtained from Food Industry Research and Development Institute (Hsinchu City, Taiwan) and courtesy of Dr San-Yuan Chen of Department of Materials Science and Engineering at National Chiao Tung University, Taiwan, respectively. Balb/c C57B nude mice were purchased from the National Laboratory Animal Center, Taiwan.

Chen H.H., Huang W.C., Chiang W.H., Liu T.I., Shen M.Y., Hsu Y.H., Lin S.C, & Chiu H.C. (2015). pH-Responsive therapeutic solid lipid nanoparticles for reducing P-glycoprotein-mediated drug efflux of multidrug resistant cancer cells. International Journal of Nanomedicine, 10, 5035-5048.

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Glyceride Standards for Analytical Methods

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Dichloromethane (GC grade; Sigma-Aldrich, Switzerland), acetonitrile (ULC/MS grade; Biosolve, France), water (LC-MS Ultra grade; Honeywell, Germany), 2-propanol (ULC/MS grade; Biosolve, France), formic acid (ULC/MS grade; Biosolve, France), ammonium formate (LC-MS Ultra grade; Fluka, Switzerland), dimyristin (DG 28:0), dipalmitolein (DG 32:2), dipalmitin (DG 32:0), diolein (DG 36:2) and distearin (DG 36:0) (all >99%; Nu-Chek Prep, Inc, USA), tricaprilin (TG 24:0), tricaprin (TG 30:0), trilaurin (TG 36:0), trimyristin (TG 42:0) and tripalmitin (48:0) (all 99.9%; Sigma-Aldrich, USA) were used as received.
Stock solutions of glycerides were prepared in dichloromethane. A 1 μM glyceride mixture in 2 : 1 : 1 isopropanol/ acetonitrile/water was used as a quality control standard. All standard solutions were stored at -24 °C before and after analysis to prevent degradation and solvent evaporation.

Frick AA ., Kummer N ., Moraleda A , & Weyermann C . (2020). Changes in latent fingermark glyceride composition as a function of sample age using UPLC-IMS-QToF-MS^E. The Analyst, 145(12).

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Enzymatic Interesterification of RBDO

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RBDO with iodine value (IV) of 60 was obtained from PT. Salim Ivomas TBK, Indonesia. Tricaprylin, molecular sieve 4 Å and triglyceride standard mixture (tricaprin, Tricaprylin, trilaurin, trimyristin, and tripalmitin) were purchased from Sigma-Aldrich, Singapore. Lipozyme TL IM was obtained from Novozyme A/S, Denmark. Hexane, chloroform, ethanol, octanol, sodium hydroxide, acetonitrile, and acetone were analytical grade and purchased from Merck, Germany.

Utama Q.D., Sitanggang A.B., Adawiyah D.R., & Hariyadi P. (2021). Lipase-catalyzed transesterification of medium-long-medium structured lipid (MLM-SL) using palm olein and tricaprylin in packed-bed reactor (PBR). Emirates Journal of Food and Agriculture.

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Optimized HPLC-MS Lipid Quantification

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Acetonitrile (ACN, ultragradient grade for HPLC, min. 99.9%, Chemsolute) was from Th. Geyer (Renningen, Germany) and ammonium formate (NH 4 HCOO, for LC-MS) was from Fisher Scientific (Schwerte, Germany). tert-Butyl methyl ether (TBME, ≥ 99.8%, for HPLC, Chromasolv), formic acid (HCOOH, ~ 98%, for LC-MS), and iso-propanol (≥ 99.9%, LC-MS, Chromasolv) were obtained from Sigma-Aldrich (Steinheim, Germany) and ethanol (absolute, > 99.7%, gradient grade for HPLC, HiPerSolv Chromanorm) was purchased from VWR International (Bruchsal, Germany). Lauric acid, myristic acid, palmitic acid (PA), stearic acid, palmit oleic acid, oleic acid (all analytical standard grade, > 99.5%), 1-monolaurin, 1-monomyristin, 1-monopalmitin (1-MP), 1-monostearin, 1-monoolein (all ≥ 99%), 1,2-distearin (> 99%), 1,3-diolein (≥ 97%), trilaurin, trimyristin, tripalmitin (TP), tristearin, and triolein (all > 99%) were from Sigma-Aldrich.
, and 1,3-distearin (all > 99%) were purchased from Larodan (Malmö, Sweden). Nucleodur Gravity-SB C18 column (150 mm × 3 mm, 3 µm) was from Macherey-Nagel (Düren, Germany). Several E 471 emulsifiers (distilled MG and MG/DG emulsifiers) were provided from different producers.

Schick D., Link K., Schwack W., Granvogl M, & Oellig C. (2021). Analysis of mono-, di-, triacylglycerols, and fatty acids in food emulsifiers by high-performance liquid chromatography–mass spectrometry. Eur Food Res Technol., 247(4).

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