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Cellulose

Cellulose, a natural polysaccharide found in plant cell walls, is a versatile biomaterial with diverse applications in fields such as papermaking, textiles, and biomedicine.
This structural component of plants consists of long chains of glucose units linked by beta-1,4-glycosidic bonds.
Cellulose exhibits remarkable properties, including high tensile strength, biodegradability, and the ability to be chemically modified.
Researchers leverage these characteristics to develop novel cellulose-based products and optimixe production processes.
PubCompare.ai's AI-driven tools can help accelerate cellulose-related discoveries by identifying the best protocols and products from the literature, preprints, and patents.
Seamless collaboration and reproducible research are key to unlocking the full potential of this renewable resource.

Most cited protocols related to «Cellulose»

1
Two-Stage Sulfuric Acid Hydrolysis for Lignin Analysis
The use of a two-stage sulfuric acid hydrolysis for the analysis of lignin dates to the turn of the 20th century, although the use of concentrated acid to release sugars from wood dates to the early 19th century (7 ). Klason, in 1906, is often credited as the first to use sulfuric acid to isolate lignin from wood (7 −9 ). The method became named after Klason, and the insoluble residue from the test is known as “Klason lignin.” An English translation of a Klason paper, from this period (10 ), describes his attempt to determine the structure of spruce wood lignin. According to Brauns (7 ), Klason’s method originally used 72 wt % sulfuric acid; he later reduced this to 66 wt % to gelatinize the wood. He filtered the solids and subjected them to a second hydrolysis in 0.5 wt % hydrochloric acid.
Although Klason is generally credited as being the first to use sulfuric acid for lignin analysis, Sherrard and Harris (11 ) credit the use of sulfuric acid to Fleschsig in 1883, Ost and Wilkening in 1912, and König and Rump in 1913. According to Harris (12 ), Fleschsig, in 1883, dissolved cotton cellulose and converted it nearly quantitatively into sugars using strong sulfuric acid followed by dilution and heating. According to Browning (13 ), Ost and Wilkening introduced the use of 72 wt % sulfuric acid for lignin determinations in 1910. A translated paper by Heuser (14 ) credited König and Ost and Wilkening for the sulfuric acid lignin method. Dore (15 ) described several improved analytical methods (cellulose, lignin, soluble pentosans, mannan, and galactan) for the summative analysis of coniferous woods. The discrepancies in attribution may be due to differing definitions for the method cited (e.g., first to use acid to determine lignin, first to use sulfuric acid, first to use 72 wt % sulfuric acid, etc.) and to missed citations across continental distances in the early 20th century.
Sluiter J.B., Ruiz R.O., Scarlata C.J., Sluiter A.D, & Templeton D.W. (2010). Compositional Analysis of Lignocellulosic Feedstocks. 1. Review and Description of Methods. Journal of Agricultural and Food Chemistry, 58(16), 9043-9053.
Publication 2010
Acids Cellulose Galactans Gossypium Hydrochloric acid Hydrolysis Lignin Mannans Pentosan Sulfuric Polyester Picea Sugars sulfuric acid Technique, Dilution Tracheophyta Xylose
2
Cellulose Crystallinity Determination by XRD and NMR
The CI of the eight celluloses was measured by two different techniques: XRD and solid-state 13C NMR. XRD was performed on a four-circle goniometer (XDS-2000 Polycrystalline Texture Stress (PTS) goniometer; Scintag, Scintag Inc., Cupertino, CA, USA) using CuKα radiation generated at 45 kV and 36 mA. The CuKα radiation consists of Kα1 (0.15406 nm) and Kα2 (0.15444 nm) components, and the resultant XRD data has both components present; the CuKα radiation is filtered out from the data using a single-channel analyzer on the output from the semiconductor detector, and does not contribute to the data. The source slits were 2.0 mm and 4.0 mm at a 290 mm goniometer radius, and the detector slits were 1.0 mm and 0.5 mm at the same radius. Dried cellulose samples (approximately 0.5 g) were mounted onto a quartz substrate using several drops of diluted glue. This diluted glue is amorphous when it is dry, and adds almost no background signal (lower line in Figure 1a). Scans were obtained from 5 to 50 degrees 2θ in 0.05 degree steps for 15 seconds per step.
To calculate the CI of cellulose from the XRD spectra, three different methods were used. First, CI was calculated from the height ratio between the intensity of the crystalline peak (I002 - IAM) and total intensity (I002) after subtraction of the background signal measured without cellulose [17 (link)-19 (link)] (Figure 1a). Second, individual crystalline peaks were extracted by a curve-fitting process from the diffraction intensity profiles [20 (link),21 (link)]. A peak fitting program (PeakFit; www.systat.com) was used, assuming Gaussian functions for each peak and a broad peak at around 21.5° assigned to the amorphous contribution (Figure 1b). Iterations were repeated until the maximum F number was obtained. In all cases, the F number was >10,000, which corresponds to a R2 value of 0.997. Third, ball-milled cellulose (Figure 2c) was used as amorphous cellulose to subtract the amorphous portion from the diffraction profiles [15 (link)] (Figure 1c). After subtracting the diffractogram of the amorphous cellulose from the diffractogram of the whole sample, the CI was calculated by dividing the remaining diffractogram area due to crystalline cellulose by the total area of the original diffractogram.
Solid-state 13C NMR spectra were collected at 4.7 T with cross-polarization and magic angle spinning (MAS) in a 200 MHz spectrometer (Avance; Bruker, Madison, WI, USA). Variable amplitude cross-polarization was used to minimize intensity variations of the non-protonated aromatic carbons that are sensitive to Hartmann-Hahn mismatch at higher MAS rotation rates [22 ]. The 1H and 13C fields were matched at 53.6 kHz, and a 1 dB ramp was applied to the proton rotating-frame during the matching period. Acquisition time was 0.051 seconds, and sweep-width was 20 kHz. MAS was performed at 6500 Hz. The number of scans was 10,000 to 20,000 with a relaxation time of 1.0 seconds. The CI was determined by separating the C4 region of the spectrum into crystalline and amorphous peaks, and calculated by dividing the area of the crystalline peak (87 to 93 ppm) by the total area assigned to the C4 peak (80 to 93 ppm) [23 (link)] (Figure 3a, Figure 3b).
Park S., Baker J.O., Himmel M.E., Parilla P.A, & Johnson D.K. (2010). Cellulose crystallinity index: measurement techniques and their impact on interpreting cellulase performance. Biotechnology for Biofuels, 3, 10.
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Publication 2010
Carbon Carbon-13 Magnetic Resonance Spectroscopy Cellulose Neoplasm Metastasis Protons Quartz Radionuclide Imaging Radiotherapy Radius Reading Frames
3
Integrated 1G + 2G Bioethanol Production
The integrated plant was modeled assuming a 1G raw material loading of 360,000 tons dry grain per year and a 2G raw material loading of 180,000 tons dry wheat straw per year. These raw material loadings correspond to an estimated annual ethanol production of 200,000 m3, assuming C6 fermentation only. In some of the simulated cases, C5 fermentation was also considered, which increased the annual ethanol production to approximately 230,000 m3. It was assumed that the plant was in operation 8000 h per year, and could be managed by 28 people. One 1G case and six integrated 1G + 2G cases were modeled. In the integrated cases, ethanol, DDGS, and biogas production from the C5 sugars were investigated, as well as biogas upgrading to vehicle fuel quality. A sensitivity analysis was also performed for the six integrated cases to assess variations in the biogas yield which increased the investigated configurations to another six supplementary cases.
An overview of the process is shown in Fig. 11, and further details are provided in Section “Case description” below.

Schematic overview of the 1G + 2G process and alternative configurations

Simulations were performed with the flow sheeting program Aspen Plus (version 8.2 from Aspen Technology Inc., Massachusetts, USA). Data for biomass components such as cellulose and lignin were retrieved from the National Renewable Energy Laboratory (NREL) database developed for biofuel components [28 ]. The NRTL-HOC property method was used for all units except in the heat and power production steam cycle, where STEAMNBS was used. The simulation models were further developments of previous work by Wingren et al. [29 (link), 30 (link)], Sassner and Zacchi [31 (link)] and Joelsson et al. [32 ]. Heat integration was implemented as described previously [32 ] using Aspen Energy Analyzer (version 8.2). The results from Aspen Plus were implemented in APEA, and were used together with vendors’ quotations to evaluate the capital and operational costs. Further details on the Aspen Plus modeling can be found in a previous publication [33 (link)].
Joelsson E., Erdei B., Galbe M, & Wallberg O. (2016). Techno-economic evaluation of integrated first- and second-generation ethanol production from grain and straw. Biotechnology for Biofuels, 9, 1.
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Publication 2016
Biofuels Biogas Cellulose Cereals Ethanol Fermentation Hypersensitivity Lignin Plants Steam Sugars Triticum aestivum
4
Immunolocalization of Cell Wall Markers in Flowers
Two flowers per day from anthesis, two and three days after pollination were fixed in 4% formaldehyde freshly prepared from paraformaldehyde in 1x phosphate saline buffer (PBS) pH7.3, left overnight at 4ºC, and conserved then at 0.1% formaldehyde solution [83 (link)]. Then the pistils were dehydrated in an acetone series (30%, 50%, 70%, 90%, 100%), and embedded in Technovit 8100 (Kulzer and Co, Germany) for two days. The resin was polymerized at 4ºC, and sectioned at 4 μm thickness. Sections were placed in a drop of water on a slide covered with 2% (3-Aminopropyl) triethoxysilane - APTEX (Sigma-Aldrich), and dried at room temperature. Callose was identified with the anticallose antibody (AntiCal) that recognises linear β-(1,3)-glucan segments (anti-β-(1,3)-glucan; immunoglobulin G1), Biosupplies, Australia [49 (link)]. As a secondary antibody, Alexa 488 fluorescein isothiocyanate (FITC)-conjugated anti-mouse IgG was used (F-1763; Sigma). Additionally, a monoclonal antibody (mAbs) JIM13 [84 (link)] against AGPs glycosyl epitopes, and one mAb JIM11 [85 (link)] against extensin epitopes were obtained from Carbosource Services (University of Georgia, USA). Secondary antibodies were anti-rat IgG conjugated with the same Alexa 488 used above. Sections were incubated for 5 min in PBS pH7.3 followed by 5% bovine serum albumin (BSA) in PBS for 5 min. Then, sections were incubated at room temperature for 1h with AntiCal primary mAb, JIM13, and JIM11. After that, three washes in PBS of 5 minutes each preceded the incubation for 45 min in the dark with a 1/25 diluted secondary fluorescein isothiocyanate (FITC) conjugated with the antibody in 1% BSA in PBS, followed by three washes in PBS [83 (link)]. Sections were counterstained with calcofluor white for cellulose [86 (link)], mounted in PBS or Mowiol, and examined under a LEICA DM2500 epifluorescence microscope connected to a LEICA DFC320 camera. Filters were 355/455 nm for calcofluor white and 470/525 nm for the Alexa 488 fluorescein label of the antibodies (White Level?=?255; Black Level = 0; ϒ?=?1). Exposur (Exp) times were adapted to the best compromise in overlapping photographs for each antibody: AntiCal, Exp.?=?15.30ms (Calcofluor Exp. = 1.20ms); JIM13 Exp.?=?2.52ms (Calcofluor?=?0.41ms); JIM11, Exp. = 31.59 ms (Calcofluor Exp. = 1.40ms). Brightness and contrasts were adjusted to obtain the sharpest images with the Leica Application Suite software.
Losada J.M, & Herrero M. (2014). Glycoprotein composition along the pistil of Malus x domestica and the modulation of pollen tube growth. BMC Plant Biology, 14, 1.
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Publication 2014
3-(triethoxysilyl)propylamine Acetone anti-IgG Antibodies Bos taurus Buffers calcofluor white callose Cellulose Contrast Media Epitopes Flowers Fluorescein Formaldehyde Formalin Glucans Immunoglobulins isothiocyanate Mice, House Microscopy Orosomucoid paraform Phosphates Pistil Pollination Resins, Plant Saline Solution Serum Albumin Serum Albumin, Bovine
5
Comprehensive Phytohormone Extraction and Quantification
Samples were prepared using a modified crude extraction procedure that was originally reported by Pan et al. [27 (link)]. Three replicates of each frozen leaf sample (~100 mg for each replicate) were ground to a fine power in liquid nitrogen using a mortar and pestle. Each sample was weighed into a 1.5-mL tube, mixed with 750 μL cold extraction buffer (methanol:water:acetic acid, 80:19:1, v/v/v) supplemented with internal standards, 10 ng 2H6ABA, 10 ng DHJA, 5 ng D2-IAA, and 3 μg NAA, vigorously shaken on a shaking bed for 16 h at 4°C in dark, and then centrifuged at 13,000 rpm for 15 min at 4°C. The supernatant was carefully transferred to a new 1.5-mL tube and the pellet was remixed with 400 μL extraction buffer, shaken for 4 h at 4°C, and centrifuged. The two supernatants were combined and filtered using a syringe-facilitated 13-mm diameter nylon filter with pore size 0.22 μm (Nylon 66; Jinteng Experiment Equipment Co., Ltd, Tianjing, China). The filtrate was dried by evaporation under the flow of nitrogen gas for approximately 4 h at room temperature, and then dissolved in 200 μL methanol. A aliquot of dissolved sample was further diluted 100 times using methanol for quantification of SA, because rice contains a high level of SA.
To determine whether different types of filters would influence the recovery rates of analytes, each standard (5 ng) was added into a 1.5-mL tube, mixed with the same amount of cold extraction buffer, vigorously shaken on a shaking bed, and centrifuged as described above. The samples were then filtered using a nylon filer or a syringe-facilitated 13-mm diameter cellulose filter with pore size 0.22 μm (MCE; Navigator Lab Instrument Co., Ltd, Tianjing, China). The filtrates were dried and then dissolved in methanol as described above.
For comparison, samples were also prepared using a solid-phase extraction procedure [16 (link)]. In brief, ground sample powder was mixed with 2 ml extraction buffer and shaken on a shaking bed for 16 h as for the above-described preparation for crude extraction, and then centrifuged at 3500 g for 15 min at 4°C for collecting the supernatant. The supernatant was purified using a C18-SepPak cartridge (Waters Corporation, Milford, MA, USA) by a series of steps. The purified sample was dried by evaporation and then dissolved in 200 μL of methanol as described above for preparation for the crude extraction.
Liu H., Li X., Xiao J, & Wang S. (2012). A convenient method for simultaneous quantification of multiple phytohormones and metabolites: application in study of rice-bacterium interaction. Plant Methods, 8, 2.
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Publication 2012
Acetic Acid Buffers Cellulose Cold Temperature DNA Replication Freezing Methanol Nitrogen Nylons Oryza sativa Plant Leaves Powder Preparation H Solid Phase Extraction Syringes

Most recents protocols related to «Cellulose»

1
Porous Materials for Charged Droplet Generation
Not available on PMC !

Example 3

Probe Materials

A number of porous materials were tested to generate charged droplets for mass spectrometry. The materials were shaped into triangles having sharp tips and sample solution was then applied to the constructed probes. Data herein show that any hydrophilic and porous substrate could be used successfully, including cotton swab, textile, plant tissues as well as different papers. The porous network or microchannels of these materials offered enough space to hold liquid and the hydrophilic environment made it possible for liquid transport by capillary action. Hydrophobic and porous substrates could also be used successfully with properly selected hydrophobic solvents.

For further investigation, six kinds of commercialized papers were selected and qualitatively tested to evaluate their capabilities in analyte detection. Filter papers and chromatography paper were made from cellulose, while glass microfiber filter paper was made from glass microfiber. FIG. 19 shows the mass spectra of cocaine detection on those papers. The spectrum of glass fiber paper (FIG. 19E) was unique because the intensity of background was two orders of magnitude lower than other papers and the cocaine peak (m/z, 304) could not be identified.

It was hypothesized that the glass fiber paper was working on mode II and prohibiting efficient droplet generation, due to the relative large thickness (˜2 mm). This hypothesis was proved by using a thin layer peeled from glass fiber paper for cocaine detection. In that case, the intensity of the background increased and a cocaine peak was observed. All filter papers worked well for cocaine detection, (FIGS. 19A-19D). Chromatography paper showed the cleanest spectrum and relative high intensity of cocaine (FIG. 19F).

Probe Shape and Tip Angle

Many different probe shapes were investigated with respect to generating droplets. A preferred shape of the porous material included at least one tip. It was observed that the tip allowed ready formation of a Taylor cone. A probe shape of a triangle was used most often. As shown in FIGS. 25A-25C, the sharpness of the tip, the angle of the tip (FIGS. 27A-25B), and the thickness of the paper substrate could effect the spray characteristics. The device of a tube shape with multiple tips (FIG. 25-D) is expected to act as a multiple-tip sprayer, which should have improved spray efficiency. An array of micro sprayers can also be fabricated on a DBS card using sharp needles to puncture the surface (FIG. 25E).

US11867684B2. Sample dispenser including an internal standard and methods of use thereof (2024-01-09). Purdue Research Foundation [US]. Inventors: Zheng Ouyang [US], He Wang [US], Nicholas E. Manicke [US], Robert Graham Cooks [US], Qian Yang [US], Jiangjiang Liu [US].
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Patent 2024
Capillary Action Cellulose Chromatography Cocaine Gossypium Mass Spectrometry Medical Devices Needles Plant Cone Plants Punctures Solvents Tissues
2
Synthesis of Triazolopyrimidine Derivatives
Not available on PMC !

Example 2

[Figure (not displayed)]

N-(2-chloro-4-(trifluoromethyl)phenyl)-2-(5-ethyl-2-morpholino-7-oxo-6-(piperazin-1-yl)-[1,2,4]triazolo[1,5-a]pyrimidin-4(7H)-yl)acetamide (Intermediate B) (200 mg, 352 μmol) was suspended in DMF (5 mL). Perfluorophenyl 3-hydroxypicolinate (Intermediate CT) (215 mg, 703 μmol) and Et3N (97.0 μL, 703 μmol) were added and the RM was stirred at 70° C. for 3 hours. The RM was concentrated under reduced pressure. The crude product was first purified by column chromatography (Silica gel column: Silica 12 g, eluent DCM:MeOH 100:0 to 90:10). Then a second purification by reverse phase preparative HPLC (RP-HPLC acidic 9: 40 to 50% B in 2 min, 50 to 55% B in 10 min) afforded the title compound.

LC-MS: Rt=0.98 min; MS m/z [M+H]+ 690.6/692.6, m/z [M−H]− 688.4/690.3; UPLC-MS 1

LC-MS: Rt=4.84 min; MS m/z [M+H]+ 690.2/692.2 m/z [M−H]− 688.3/690.3; UPLC-MS 2

1H NMR (400 MHz, DMSO-d6) δ 10.37 (s, br, 1H), 10.34 (s, br, 1H), 8.05 (m, 2H), 7.96 (d, J=2.1 Hz, 1H), 7.72 (dd, J=2.1 Hz, 8.7 Hz, 1H), 7.28 (m, 2H), 5.21 (s, 2H), 4.53 (m, 1H), 3.66 (m, 4H), 3.46 (m, 3H), 3.38 (m, 4H), 3.20 (m, 1H), 2.92 (m, 3H), 2.76 (m, 1H), 2.58 (m, 1H), 1.16 (t, J=7.5 Hz, 3H)

Example 24

[Figure (not displayed)]

To the stirred solution of N-(2-chloro-6-(trifluoromethyl)pyridin-3-yl)-2-(5-ethyl-2-(4-methoxycyclohex-1-en-1-yl)-7-oxo-6-(piperazin-1-yl)-[1,2,4]triazolo[1,5-a]pyrimidin-4(7H)-yl)acetamide (Intermediate Y) (300 mg, 504 μmol), 4-chloro-3-hydroxypicolinic acid (140 mg, 807 μmol), HOBt (136 mg, 1.01 mmol) and EDC.HCl (193 mg, 1.01 mmol) in DCM (20 mL) was added pyridine (122 μL, 1.51 mmol) at 0° C. The RM was stirred at RT for 16 hours. The RM was quenched with NaHCO3 and extracted with DCM. The organic layer was dried over Na2SO4 and concentrated under reduced pressure. The crude product was purified by column chromatography (Silica gel column: Silica 4 g, eluent DCM:MeOH 100:0 to 98:2). The residue was purified by preparative chiral HPLC (instrument: Agilent 1200 series, with single quad mass spectrometer; column: LUX CELLULOSE-4, 250 mm×21.1 mm, 5.0 μm; eluent: A=hexane, B=0.1% HCOOH in EtOH; flow rate: 15 mL/min; detection: 210 nm; injection volume: 0.9 mL; gradient: isocratic: 50(A):50(B)).

Example 24a: The product containing fractions were concentrated at 40° C. and washed with n-pentane (5×10 mL), decanted and dried to give the title compound as an off-white solid—first eluting stereoisomer.

Chiral HPLC (C-HPLC 2): Rt=10.764 min

LC-MS: Rt=1.08 min; MS m/z [M+H]+ 750.5/752.5, m/z [M−H]− 748.4/750.4; UPLC-MS 1

LC-MS: Rt=5.29 min; MS m/z [M+H]+ 750.2/752.2, m/z [M−H]− 748.2/750.2; UPLC-MS 2

1H NMR (400 MHz, DMSO-d6) δ 10.68 (s, br, 2H), 8.56 (d, J=8.1 Hz, 1H), 7.98 (d, J=5.6 Hz, 1H), 7.94 (d, J=8.1 Hz, 1H), 7.50 (d, J=5.1 Hz, 1H), 6.72 (m, 1H), 5.34 (s, 2H), 4.53 (m, 1H), 3.52 (m, 4H), 3.28 (m, 4H), 2.98 (m, 3H), 2.80 (m, 1H), 2.63 (m, 1H), 2.55 (m, 1H), 2.46 (m, 1H), 2.16 (m, 2H), 1.95 (m, 1H), 1.68 (m, 1H), 1.17 (t, J=7.3 Hz, 3H)

Example 24b: The product containing fractions were concentrated at 40° C. and washed with n-pentane (5×10 mL), decanted and dried to give the title compound as an off-white solid—second eluting stereoisomer.

Chiral HPLC (C-HPLC 2): Rt=18.800 min

LC-MS: Rt=1.08 min; MS m/z [M+H]+ 750.1/752.1, m/z [M−H]− 748.2/750.2; UPLC-MS 1

LC-MS: Rt=5.30 min; MS m/z [M+H]+ 750.1/752.1, m/z [M−H]− 748.2/750.2; UPLC-MS 2

1H NMR (400 MHz, DMSO-d6) δ 10.83 (s, br, 1H), 10.55 (s, br, 1H), 8.56 (d, J=8.2 Hz, 1H), 8.06 (d, J=5.3 Hz, 1H), 7.92 (d, J=8.2 Hz, 1H), 7.55 (d, J=5.3 Hz, 1H), 6.72 (m, 1H), 5.35 (s, 2H), 4.54 (m, 1H), 3.54 (m, 4H), 3.28 (m, 3H), 3.25 (m, 1H), 2.99 (m, 3H), 2.81 (m, 1H), 2.62 (m, 1H), 2.41 (m, 2H), 2.16 (m, 2H), 1.96 (m, 1H), 1.66 (m, 1H), 1.18 (t, J=7.3 Hz, 3H)

Example 25

[Figure (not displayed)]

N-(2-chloro-6-(trifluoromethyl)pyridin-3-yl)-2-(5-ethyl-2-(4-methoxycyclohex-1-en-1-yl)-7-oxo-6-(piperazin-1-yl)-[1,2,4]triazolo[1,5-a]pyrimidin-4(7H)-yl)acetamide.HCl (Intermediate Y) (120 mg, 190 μmol) and DIPEA (166 μL, 950 μmol) were dissolved in DCM (5 mL) and then 3-hydroxypicolinoyl chloride (Intermediate CV) (59.9 mg, 380 μmol) was added at 0° C. and stirred for 2 hours. 3-hydroxypicolinoyl chloride (Intermediate CV) (59.9 mg, 380 μmol) was added again and the reaction was continued under stirring for 12 hours. The RM was diluted with DCM and washed with water and aq NaHCO3 (2×20 mL), washed with water and brine, dried over Na2SO4, filtered and concentrated. The crude product was combined with another experiment and purified by column chromatography (Silica gel column: Silica 4 g, eluent DCM:MeOH 100:0 to 99:1) then further purified by reverse phase preparative HPLC (RP-HPLC acidic 10: 40 to 50% B in 2 min, 50 to 60% B in 8 min) to give the title compound as an off-white solid.

The racemate was purified by preparative chiral HPLC (instrument: Agilent 1200 series, with single quad mass spectrometer; column: CELLULOSE-4, 250 mm×21.2 mm; eluent: A=hexane, B=0.1% HCOOH in MeOH:EtOH 1:1; flow rate: 20 mL/min; detection: 210 nm; injection volume: 0.9 mL; gradient: isocratic 60(A):40(B)).

Example 25a: First eluting stereoisomer, off-white solid.

Chiral HPLC (C-HPLC 1): Rt=10.070 min

LC-MS: Rt=0.98 min; MS m/z [M+H]+ 716.5/718.6, m/z [M−H]− 714.3/716.3; UPLC-MS 1

LC-MS: Rt=4.76 min; MS m/z [M+H]+ 716.2/718.2, m/z [M−H]− 714.2/716.2; UPLC-MS 2

1H NMR (400 MHz, DMSO-d6) δ 10.46 (s, br, 2H), 8.56 (d, J=8.5 Hz, 1H), 8.05 (m, 1H), 7.90 (d, J=8.4 Hz, 1H), 7.28 (m, 2H), 6.72 (m, 1H), 5.30 (s, 2H), 4.54 (m, 1H), 3.47 (m, 4H), 3.27 (s, 3H), 3.21 (m, 1H), 2.96 (m, 3H), 2.79 (m, 1H), 2.59 (m, 3H), 2.43 (m, 1H), 2.14 (m, 1H), 1.95 (m, 1H), 1.67 (m, 1H), 1.17 (t, J=7.2 Hz, 3H)

Example 25b: Second eluting stereoisomer, off-white solid.

Chiral HPLC (C-HPLC 1): Rt=16.023 min

LC-MS: Rt=0.96 min; MS m/z [M+H]+ 716.3/718.3, m/z [M−H]− 714.3/716.3; UPLC-MS 1

LC-MS: Rt=4.77 min; MS m/z [M+H]+ 716.2/718.2, m/z [M−H]− 714.2/716.2; UPLC-MS 2

1H NMR (400 MHz, DMSO-d6) δ 10.39 (s, br, 2H), 8.56 (d, J=8.0 Hz, 1H), 8.06 (m, 1H), 7.93 (d, J=8.1 Hz, 1H), 7.28 (m, 2H), 6.72 (m, 1H), 5.32 (s, 2H), 4.54 (m, 1H), 3.46 (m, 4H), 3.27 (s, 3H), 3.20 (m, 1H), 2.96 (m, 3H), 2.79 (m, 1H), 2.59 (m, 3H), 2.41 (m, 1H), 2.14 (m, 1H), 1.95 (m, 1H), 1.68 (m, 1H), 1.17 (t, J=7.1 Hz, 3H)

US11878973B2. Bicyclic compounds and their uses (2024-01-23). NOVARTIS AG [CH]. Inventors: Vincent Bordas [FR], Jvan Brun [CH], Markus Furegati [CH], Jacques Hamon [FR], Jürgen Hans-Hermann Hinrichs [DE], Philipp Holzer [CH], Fatma Limam [FR], Henrik Möbitz [DE], Sandro Nocito [CH], Simone Plattner [DE], Niko Schmiedeberg [CH], Joseph Schoepfer [CH], Ross Sinclair Strang [FR], Frédéric Zecri [US].
Full text: Click here
Patent 2024
1-hydroxybenzotriazole 1H NMR acetamide Acids Bicarbonate, Sodium Bicyclo Compounds brine Cellulose Chlorides Chromatography DIPEA Ethanol H 718 Hexanes High-Performance Liquid Chromatographies Morpholinos pentane Piperazine Pressure pyridine Silica Gel Silicon Dioxide Stereoisomers Sulfoxide, Dimethyl Tandem Mass Spectrometry
3
Exemplary Liquisoft Capsule Compositions
Not available on PMC !

Example 1

Exemplary capsule shell and matrix compositions useful for producing Liquisoft capsules as described herein are shown in Table 4. Composition components are set forth by weight percentage of the total weight of the composition. Such compositions may be encapsulated using rotary die encapsulation as described herein.

Formulas 1 and 2 were the first shell formulations developed to achieve faster disintegration time and prevent crosslinking of the gelatin shell with matrix fill components.

TABLE 4
Exemplary Liquisoft Composition
Capsule Shell Formulation
ComponentFormula 1Formula 2
Gelatin, 250 Bloom24.3—
Gelatin, 150 Bloom—29.2
Gelatin, 100 Bloom 4.9—
Gelatin Hydrolysate——
Hydrolyzed Collagen——
Powdered Cellulose 1.9—
Maltitol—25.7
Glycerol32.019.1
Xylitol 4.8—
Sucralose——
Citric Acid— 0.5
Flavors— 0.5
Water32.325.0
TOTAL100%100%
VISCOSITY—3497 cP

US11872307B2. Liquisoft capsules (2024-01-16). PATHEON SOFTGELS INC. [US]. Inventors: YinYan Zhao [US], Yunhua Hu [US], Mervin Williams, Jr. [US], Tatyana Dyakonov [US], Saujanya Gosangari [US], Chue Yang [US], Henricus Marinus Gerardus Maria Van Duijnhoven [NL], Martin Piest [NL], Aqeel A. Fatmi [US].
Full text: Click here
Patent 2024
Capsule Cellulose Citric Acid Collagen Type I Flavor Enhancers Gelatins Glycerin maltitol sucralose Viscosity Xylitol
4
Synthesis of Spirocyclic Indazole Derivative
Not available on PMC !

Example 2

[Figure (not displayed)]

To 1-methyl-2-oxo-1-azaspiro[4.5]decan-8-yl 4-methylbenzenesulfonate (Int III-1) (1.4 g, 4.2 mmol) was added DMF (15 mL), N-(imidazo[1,2-b]pyridazin-3-yl)-6-methoxy-1H-indazole-5-carboxamide (Int II-1) (1.3 g, 4.2 mmol) and KOH (466 mg, 8.3 mmol). The resulting solution was stirred at 100° C. After 12 h the reaction mixture was allowed to cool to rt and directly purified using C18-flash chromatography (eluting with 0% to 100% MeCN in water (0.05% FA)) followed by chiral HPLC (CHIRAL ART Cellulose-SB, 2×25 mm, 5 μm; mobile Phase A: MTBE (2 mm NH3 in MeOH); mobile Phase B: i-PrOH; gradient: isocratic 50% B for 21.5 min; flow rate: 20 mL/min) to afford N-(imidazo[1,2-b]pyridazin-3-yl)-6-methoxy-2-((5s,8s)-1-methyl-2-oxo-1-azaspiro[4.5]decan-8-yl)-2H-indazole-5-carboxamide (28.0 mg, 1%) as a yellow solid. 1H NMR (300 MHz, CD3OD) δ 8.75 (d, 1H), 8.62 (s, 1H), 8.59 (d, 1H), 8.15 (s, 1H), 8.04 (dd, 1H), 7.21-7.28 (m, 2H), 4.71-4.79 (m, 1H), 4.23 (s, 3H), 2.68 (s, 3H), 2.59-2.69 (m, 2H), 2.44 (t, 2H), 2.07-2.33 (m, 6H), 1.45-1.55 (m, 2H). m/z (ESI+), [M+H]+=474.

US11866405B2. Substituted indazoles as IRAK4 inhibitors (2024-01-09). AstraZeneca AB [SE]. Inventors: Ina Terstiege [SE], Stefan Schiesser [SE], Yafeng Xue [SE], Hui-Fang Chang [SE], Anna Ingrid Kristina Berggren [SE].
Full text: Click here
Patent 2024
1H NMR Cellulose Chromatography High-Performance Liquid Chromatographies Indazoles inhibitors IRAK4 protein, human methyl tert-butyl ether
5
Sterilization of BC Non-Woven
Not available on PMC !

Example 2

BC non-woven was produced by the method of the present invention. In particular, BC non-woven was sterilized with e-beam or by exposure to steam after removal from the culture vessel and separation from the BC that remained in the culture vessel. The BC network structure was investigated with scanning electron microscopy. It was found that the network structure was neither disturbed by sterilization with steam nor by e-beam sterilization.

US11859227B2. Method for producing bacterially synthesized cellulose non-woven (2024-01-02). JENACELL GMBH [DE]. Inventors: Dana Kralisch [DE], Elena Pfaff [DE], Daniela Rossner [DE].
Full text: Click here
Patent 2024
Blood Vessel Cellulose Scanning Electron Microscopy Steam Sterilization

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