Structure of 4249-72-3
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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
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Narani, Anand ; Gao, Yu ; Zhang, Jialiang ; Beach, Connor A ; Foston, Marcus ;
Abstract: Lignin depolymerization yields a complex mixture of monomeric products, including a wide range of highly oxygenated molecules. Quantifying these lignin monomers using existing gas chromatography (GC) with a flame ionization detector and effective carbon number methods is highly challenging due to the response variability for molecules containing heteroatoms and the inability to quantify unknown monomers. In this work, we demonstrate the potential of a GC equipped with dual detectors, a modified flame ionization detector (FID) for quantitative carbon detection (Polyarc reactor) and a mass spectrometer (GC-QCD/MS) for identifying and quantifying lignin monomers without the use of standards. Lignin depolymerization products were generated from Organosolv poplar lignin and poplar biomass through methods such as hydrogenolysis, solvolysis, and reductive catalytic fractionation. In the GC-QCD/MS, the QCD component converts all organic molecules into methane before quantification via FID, providing nearly uniform response factors for diverse compounds found within the sample, while a flow splitter directs a portion of the sample to the mass spectrometer for simultaneous molecular identification. This setup enables cost-effective, flexible, and streamlined measurements of lignin monomer carbon yields without the need for standards. Additionally, GC-QCD/MS supports the quantification of unidentified compounds within the lignin product mixture.
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Jake G. Tillou ; Joseph J. Kuchta III ; Nathan Thornburg ; Santosh K. Balijepalli ; Aaron K. Vannucci ;
Abstract: The selective hydrodeoxygenation of lignin derived aromatics represents an important step towards the valorization of biomass. With this goal in mind, we synthesized a hybrid molecular/heterogeneous catalyst comprised of a (2,6-bis(1-methylbenzimidazolyl)pyridine-4′-aminopropyltrisiloxane)palladium(II) molecular catalyst covalently bound to a solid silica support through the siloxane functional group. A series of model complexes containing C–O bonds typically found in lignin biomass were explored and varying degrees of C–O bond hydrogenation were achieved. The stable covalent binding of the catalyst to the support was attributed to the observed long catalyst lifetimes which led to over 6000 catalytic turnovers without catalyst deactivation. Spectroscopic characterization of the catalyst pre- and post-catalytic reactions shows the catalyst maintains molecular integrity under the reaction conditions examined. The catalyst also exhibited complete selectivity for hydrodeoxygenation over ring hydrogenation of oxygenated aromatic molecules.
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Pham, Xuan-Tien ; Tran, Vy Anh ; Tran, Lan-Trinh Thi ; Nguyen, Tram Ngoc P ; Le, Thong Hoang ; Hoang, Huy , et al.
Abstract: The catalytic conversion of lignin model compounds was performed using Ru/C catalysts and an autoclave reactor. The Ru/C catalysts were prepared by the impregnation method using highly porous homemade activated carbon and characterized by XRD, SEM, and specific surface area. The catalytic reactions were performed in a high pressure/temperature reactor at different temperatures and with different solvents. The results showed that the novel Ru/C catalysts prepared from carbon supports activated by the KOH agent showed higher catalytic activity than the commercial catalyst. Ethanol and 2-propanol were suitable solvents for the cleavage of the β–O–4 ether bond of 2-phenoxy1-phenyl ethanol (~65–70% conversion) over a Ru/C-KOH-2 catalyst at 220 ◦C in comparison to tert-butanol and 1-propanol solvents (~43–47% conversion of 2-phenoxy-1-phenyl ethanol). Also, the increase in reaction temperature from 200 ◦C to 240 ◦C enhanced the cleavage of the ether bond with an increase in phenol selectivity from 9.4% to 19.5% and improved the catalytic conversion of 2-phenoxy-1-phenyl ethanol from 46.6% to 98.5% over the Ru/C-KOH-2 catalyst and ethanol solvent. The Ru/C-KOH-2 catalyst showed outstanding conversion (98.5%) of 2-phenoxy-1-phenylethanol at 240 ◦C, 1 h, ethanol solvent. This novel hierarchical porous activated carbon-supported ruthenium catalyst (Ru/C-KOH-2) can be applied for the further conversion of the lignin compound.
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Keywords: active carbon ; biochar ; Ru/C ; lignin ; β-O-4 aryl ether
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Fast screening of Depolymerized Lignin Samples Through 2D‐Liquid Chromatography Mapping
De Saegher, Tibo ; Lauwaert, Jeroen ; Vercammen, Joeri ; Van Geem, Kevin M ; De Clercq, Jeriffa ; Verberckmoes, An
Abstract: Lignin valorization and particularly its depolymerization into bio‐aromatics, has emerged as an important research topic within green chemistry. However, screening of catalysts and reaction conditions within this field is strongly constrained by the lack of analytical techniques that allow for fast and detailed mapping of the product pools. This analytical gap results from the inherent product pool complexity and the focus of the state‐of‐the‐art on monomers and dimers, overlooking the larger oligomers. In this work, this gap is bridged through the development of a quasi‐orthogonal GPC‐HPLC‐UV/VIS method that is able to separate the bio‐aromatics according to molecular weight (hydrodynamic volume) and polarity. The method is evaluated using model compounds and real lignin depolymerization samples. The resulting color plots provide a powerful graphical tool to rapidly assess differences in reaction selectivity towards monomers and dimers as well as to identify differences in the oligomers.
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CAS No. : | 4249-72-3 |
Formula : | C14H14O2 |
M.W : | 214.26 |
SMILES Code : | OC(C1=CC=CC=C1)COC2=CC=CC=C2 |
MDL No. : | MFCD09880900 |
Boiling Point : | No data available |
InChI Key : | GSBICRJXEDSPTE-UHFFFAOYSA-N |
Pubchem ID : | 572254 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 16 |
Num. arom. heavy atoms | 12 |
Fraction Csp3 | 0.14 |
Num. rotatable bonds | 4 |
Num. H-bond acceptors | 2.0 |
Num. H-bond donors | 1.0 |
Molar Refractivity | 63.39 |
TPSA ? Topological Polar Surface Area: Calculated from |
29.46 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.33 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
2.74 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
2.47 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
2.68 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
2.96 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
2.64 |
Log S (ESOL):? ESOL: Topological method implemented from |
-3.19 |
Solubility | 0.14 mg/ml ; 0.000652 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-3.01 |
Solubility | 0.208 mg/ml ; 0.00097 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-4.54 |
Solubility | 0.00618 mg/ml ; 0.0000288 mol/l |
Class? Solubility class: Log S scale |
Moderately soluble |
GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg |
High |
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg |
Yes |
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) |
No |
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) |
Yes |
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) |
No |
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) |
No |
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) |
Yes |
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) |
No |
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from |
-5.66 cm/s |
Lipinski? Lipinski (Pfizer) filter: implemented from |
0.0 |
Ghose? Ghose filter: implemented from |
None |
Veber? Veber (GSK) filter: implemented from |
0.0 |
Egan? Egan (Pharmacia) filter: implemented from |
0.0 |
Muegge? Muegge (Bayer) filter: implemented from |
0.0 |
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat |
0.55 |
PAINS? Pan Assay Interference Structures: implemented from |
0.0 alert |
Brenk? Structural Alert: implemented from |
0.0 alert: heavy_metal |
Leadlikeness? Leadlikeness: implemented from |
No; 1 violation:MW<1.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
2.2 |
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