Coriander (Coriandrum sativum L.) seeds were purchased from a local food store in Warsaw, Poland, whereas almonds (Prunus dulcis) and hazelnuts (Corylis avellana L.) were obtained from the Hebar Company, Poland. The yeast strain of Y. lipolytica W29 (ATCC20460) was obtained from the culture collection of the Food and Microbiology Processing and Engineering Laboratory (GPMA) at the University of Burgundy/AgroSup, France. The strain was stored in 10% glycerol in freezing conditions (−80 °C). All medium ingredients (agar–agar, yeast extract, peptone, and glucose) were obtained from BTL Łódź, Poland. Sodium chloride, methyl and ethyl alcohol (99.8%), chloroform, ethyl acetate, n-hexane, toluene, and anhydrous magnesium sulfate were purchased from POCH, Poland, a division of Avantor Performance Products (Center Valley, PA, USA). Trolox (6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid), DPPH (2,2-diphenyl-1-picrylhydrazyl), Folin-Ciocalteu’s phenol reagent, and gallic acid were obtained from Sigma-Aldrich Chemicals, Poznan, Poland. p-Nitrophenyl laurate was synthesized at our laboratory from lauroyl chloride (Sigma-Aldrich) and p-nitrophenol (POCH), according to a method described by Vogel et al. [12 ]. All reagents used were of analytical grade.
Lauroyl chloride
Manufactured by Merck Group
Sourced in United States
Lauroyl chloride is a chemical compound used as a laboratory reagent. It is a colorless or pale-yellow liquid with a pungent odor. Lauroyl chloride is commonly used in organic synthesis reactions as an acylating agent.
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Lab products found in correlation
Palmitoyl chloride, by Merck Group (2 mentions)
P nitrophenyl laurate, by Merck Group (1 mentions)
Folin ciocalteu s phenol reagent, by Merck Group (1 mentions)
2 2 diphenyl 1 picrylhydrazyl (dpph), by Merck Group (1 mentions)
Gallic acid, by Merck Group (1 mentions)
Trolox, by Merck Group (1 mentions)
Octanoyl chloride, by Merck Group (1 mentions)
Rutin hydrate, by Merck Group (1 mentions)
Catechin hydrate, by Merck Group (1 mentions)
Quercetin, by Merck Group (1 mentions)
Epicatechin, by Merck Group (1 mentions)
Arium pro system, by Sartorius (1 mentions)
Sodium chloride (nacl), by Avantor (1 mentions)
Potassium chloride (kcl), by Avantor (1 mentions)
Sodium hydroxide (naoh), by Avantor (1 mentions)
Oleoyl chloride, by Merck Group (1 mentions)
Hesperetin, by Merck Group (1 mentions)
4 nitrobenzoyl chloride, by Merck Group (1 mentions)
Drx 500, by Bruker (1 mentions)
Succinic anhydride, by Merck Group (1 mentions)
10 protocols using lauroyl chloride
1
Coriander, Almonds, and Hazelnuts Characterization
2
Phenolic Compounds Extraction and Derivatization
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Commercial standards include (+)-catechin hydrate (≥98%), (−)-epicatechin (≥90%), rutin hydrate (≥95%) and quercetin (≥95%) were purchased from Sigma-Aldrich (Auckland, New Zealand). Acetonitrile (MeCN, HPLC grade), L-(+)-tartaric acid (reagent grade), acetone (analytical grade) and ethanol (analytical grade) were purchased from ECP (Auckland, New Zealand). Glacial acetic acid (AcOH, HPLC grade) was purchased from ThermoFisher Scientific (Auckland, New Zealand). Ultrapure water (H2O) had resistivity of 18.2 MΩ cm and was obtained from Sartorius Arium® Pro system. Pinot noir grape pomace (seeds, skins and stems) was industrially sourced from a New Zealand vineyard in 2015. Acylating agents (octanoyl chloride, lauroyl chloride and palmitoyl chloride) were purchased from Sigma-Aldrich (Auckland, New Zealand).
3
Amaranth Seed Modification Protocol
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Seeds of Amaranthus hypochondriacus from cultivar Nutrisol were donated by the National Research Institute in Forestry, Agriculture and Livestock, México (INIFAP). Lauroyl chloride was purchased from Sigma-Aldrich Chemical Co. (Toluca de Lerdo, México). The analytical grade salts NaOH, LiCl, CH3CO2K, KCl, K2CO3, Mg(NO3)2, NaCl, KCl, NaHSO3 and BaCl were purchased from J. T. Baker® (Phillipsburg, NJ, USA).
4
Synthesis of Novel Acyl Chlorides
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Hesperetin, Oleoyl chloride, Lauroyl chloride, Palmitoyl chloride, 4-nitrobenzoyl chloride, and Methoxyacetyl chloride, were bought from Sigma-Aldrich Chemicals Pvt. Ltd, USA. Triethylamine, Sodium sulphate, and solvents were bought from SRL, India. It comes with high purity so we can use it without any further purification. Column chromatography was performed on Silica Gel 60 (100–200 mesh). 1H &13C NMR spectra were recorded on Bruker DRX 500. Elemental analyses were performed using Perkin-Elmer 2400 elemental analyzer and optical rotations were determined by using a Rudolph Autopol II digital polarimeter.
5
Agave Fructan Fractions: Antimicrobial Evaluation
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The native agave fructans (NAF) were donated by the national agave producer (Nutriagaves de México S.A. de C.V). The two agave fructan fractions, high-performance (HPAF) and a high degree of polymerization (HDPAF), were obtained according to Ceja-Medina et al. [3 (link)]. Lauroyl chloride #156930 (98% purity) and succinic anhydride #239690 (purity ≥ 99%) were obtained from Sigma Aldrich, (St. Louis, MO, USA), acetic anhydride #0655 (ACS purity, ≥ 97%) from Reactivos Química MEYER, (CDMX, Mexico) and N, N-dimethylformamide (DMF) # 03971 Fermont, (Monterrey, NL, Mexico). Broth and MRS agar (DifcoTM) were obtained from Thermo Fisher Scientific, MA, USA, (CDMX, Mexico) and BHI medium from MCD-LAB (Edo.de Mex., Mexico). Solutions were prepared with distilled water. Bacterial strains, Staphylococcus aureus (S. aureus, ATCC 25923), Escherichia coli (E. coli, ATCC 25922), Salmonella typhi (S. typhi, ATCC 14028) and Enterococcus faecalis (E. faecalis, ATCC 19433) were cultured at the Universidad Popular Autonoma del Estado de Puebla, Mexico.
6
Kraft Lignin Derivatization Protocol
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Kraft lignin was supplied
as BioPiva 395 by UPM Biochemicals (Germany/Finland), toluene (99.8%,
anhydrous), dimethylformamide (DMF, 99.8%, anhydrous), dimethyl sulfoxide
(DMSO, ≥99.9%, ACS reagent), n-decane (≥95%),
2-methyl tetrahydrofuran (MeTHF, ≥99.5%, ReagentPlus), Cellite
535 filtration aid (SiO2, particle size 0.02–0.1
mm), and lauroyl chloride (98%) were purchased from Sigma-Aldrich
(Norway). Pyridine (≥99.7%, analytical reagent for KarlFischer
titration) and stearoyl chloride (≥97.0%, TCI Europe) were
obtained from VWR (Norway). Ethanol (99.7%, technical grade) and 2-propanol
(99.5%, technical grade) were acquired from KiiltoClean (Norway).
Petroleum distillate was purchased as Blåtind White Spirit
from Wilhelmsen Chemicals AS, (Norway). Fumed silica (commercial name
AEROSIL 200) was supplied by Evonik Industries (Germany). Distilled
water was further purified via a Milli-Q system from Millipore to
a resistivity of 18.2 MΩ × cm.
as BioPiva 395 by UPM Biochemicals (Germany/Finland), toluene (99.8%,
anhydrous), dimethylformamide (DMF, 99.8%, anhydrous), dimethyl sulfoxide
(DMSO, ≥99.9%, ACS reagent), n-decane (≥95%),
2-methyl tetrahydrofuran (MeTHF, ≥99.5%, ReagentPlus), Cellite
535 filtration aid (SiO2, particle size 0.02–0.1
mm), and lauroyl chloride (98%) were purchased from Sigma-Aldrich
(Norway). Pyridine (≥99.7%, analytical reagent for KarlFischer
titration) and stearoyl chloride (≥97.0%, TCI Europe) were
obtained from VWR (Norway). Ethanol (99.7%, technical grade) and 2-propanol
(99.5%, technical grade) were acquired from KiiltoClean (Norway).
Petroleum distillate was purchased as Blåtind White Spirit
from Wilhelmsen Chemicals AS, (Norway). Fumed silica (commercial name
AEROSIL 200) was supplied by Evonik Industries (Germany). Distilled
water was further purified via a Milli-Q system from Millipore to
a resistivity of 18.2 MΩ × cm.
7
Bacterial Strain Cultivation and Characterization
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Lauroyl chloride (LC), glycerol, dimethyl sulfoxide (DMSO), hexadecane, sodium chloride (NaCl), potassium chloride (KCl), disodium hydrogen phosphate (Na2HPO4), potassium dihydrogen phosphate (KH2PO4), TWEEN® 80, sodium carbonate (Na2CO3) and 40,6-Diamidino-2-phenylindole (DAPI) were purchased from Sigma-Aldrich, Steinheim, Germany. BODIPY™ 493/503 (4,4-Difluoro-1,3,5,7,8-
Pentamethyl-4-Bora-3a,4a-Diaza-s-Indacene) was bought from ThermoFisher Scientific, Molecular Probes, Eugene, OR, USA. Medium-chain triglyceride (MCT) oil was a gift from AAK AB (publ.), Karlshamn, Sweden.
Lactobacillus rhamnosus GG (LGG) was bought from Collections of Micro-organisms BCCM, Ghent, Belgium.
MRS broth (de Man, Rogosa and Sharpe), MRS agar, and atmosphere generation system (AnaeroGen sachets) were bought from Oxoid, Basingstoke, England. MRS broth and agar were sterilized in an autoclave (115 °C, 15 min). All the chemicals were used as received. MilliQ water (18.2 MΩcm at 25 °C) was used in all the experiments.
Pentamethyl-4-Bora-3a,4a-Diaza-s-Indacene) was bought from ThermoFisher Scientific, Molecular Probes, Eugene, OR, USA. Medium-chain triglyceride (MCT) oil was a gift from AAK AB (publ.), Karlshamn, Sweden.
Lactobacillus rhamnosus GG (LGG) was bought from Collections of Micro-organisms BCCM, Ghent, Belgium.
MRS broth (de Man, Rogosa and Sharpe), MRS agar, and atmosphere generation system (AnaeroGen sachets) were bought from Oxoid, Basingstoke, England. MRS broth and agar were sterilized in an autoclave (115 °C, 15 min). All the chemicals were used as received. MilliQ water (18.2 MΩcm at 25 °C) was used in all the experiments.
8
Tamoxifen Citrate Nanogel Formulation
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Tamoxifen citrate was obtained from ArEx Laboratories (Mumbai). βCD was obtained from Roquette, India. Lauroyl chloride was purchased from (Merck-Sigma Aldrich, USA). Triethylamine (TEA), dry N, N-dimethylformamide (Dry DMF), dichloromethane (DCM), and other HPLC grade solvents were purchased from Merck, India. Kolliphor P 407 was procured from BASF, India. Mannitol (Perlitol™) was obtained from Signet Corporation, India. Dialysis membrane of the molecular weight cut off 12-14 kDa was purchased from Hi-media, India. MCF-7 cells were procured from ATCC, and HDMEC cells were procured from PromoCell GmbH. [3-(4,5-dimethylthiazol-2-yl)-2,5diphenyltetrazolium bromide] (MTT) were purchased from Invitrogen. Freshly prepared double distilled water and buffers filtered through 0.22 µm membrane filter (Merck Millipore, India) was used where ever required.
9
Synthesis and Characterization of Polyelectrolyte Microcapsules
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Most of the starting materials were purchased from Sigma Aldrich or POCH and used as received. 3,3′-iminobis(N,N-dimethylpropylamine) and lauroyl chloride were purchased from Aldrich Chemical Co. (Milwaukee, WI), hydrochloric acid was purchased from POCH (Gliwice, Poland). Other reagents and solvents were of commercial grade and were not additionally purified before use. Nuclear magnetic resonance (1H NMR) spectra were recorded for solutions of samples in CDCl3 using a Bruker Avance DRX300 spectrometer (Bruker, Karlsruhe, Germany). Silicone oil (SO, from Stearinerie Dubois Fils, France) was used as the oil phase. Poloxamer 403 (polymer) was obtained from BASF (Ludwigshafen, Germany). Polyelectrolytes: Chitosan (medium molecular weight), dextran sulfate sodium salt (Mw ~40 000), poly(diallyldimethylammonium) chloride (PDADMAC, Mw ~100 000–200 000, 20% in water), and polysodium 4-styrenesulphonate (PSS, Mw = 70 000) were obtained from Sigma-Aldrich. Water used for all experiments was doubly distilled and purified by means of a Millipore (Bedford, MA) Milli-Q purification system.
10
Synthesis of Glycol Ester Derivatives
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