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Structure of 4249-72-3

Chemical Structure| 4249-72-3

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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.

Purchased from AmBeed:

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 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 of oxygenated aromatic molecules.

Purchased from AmBeed:

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.

Keywords: active carbon ; biochar ; Ru/C ; lignin ; β-O-4 aryl ether

Purchased from AmBeed: ;

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.

Purchased from AmBeed:

Alternative Products

Product Details of [ 4249-72-3 ]

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

Safety of [ 4249-72-3 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Computational Chemistry of [ 4249-72-3 ] Show Less

Physicochemical Properties

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
Ertl P. et al. 2000 J. Med. Chem.

29.46 Ų

Lipophilicity

Log Po/w (iLOGP)?

iLOGP: in-house physics-based method implemented from
Daina A et al. 2014 J. Chem. Inf. Model.

2.33
Log Po/w (XLOGP3)?

XLOGP3: Atomistic and knowledge-based method calculated by
XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry

2.74
Log Po/w (WLOGP)?

WLOGP: Atomistic method implemented from
Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.

2.47
Log Po/w (MLOGP)?

MLOGP: Topological method implemented from
Moriguchi I. et al. 1992 Chem. Pharm. Bull.
Moriguchi I. et al. 1994 Chem. Pharm. Bull.
Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.

2.68
Log Po/w (SILICOS-IT)?

SILICOS-IT: Hybrid fragmental/topological method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

2.96
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

2.64

Water Solubility

Log S (ESOL):?

ESOL: Topological method implemented from
Delaney JS. 2004 J. Chem. Inf. Model.

-3.19
Solubility 0.14 mg/ml ; 0.000652 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble
Log S (Ali)?

Ali: Topological method implemented from
Ali J. et al. 2012 J. Chem. Inf. Model.

-3.01
Solubility 0.208 mg/ml ; 0.00097 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble
Log S (SILICOS-IT)?

SILICOS-IT: Fragmental method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

-4.54
Solubility 0.00618 mg/ml ; 0.0000288 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Moderately soluble

Pharmacokinetics

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)
and tested on 415 molecules (test set)
10-fold CV: ACC=0.72 / AUC=0.77
External: ACC=0.88 / AUC=0.94

No
CYP1A2 inhibitor?

Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.83 / AUC=0.90
External: ACC=0.84 / AUC=0.91

Yes
CYP2C19 inhibitor?

Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.80 / AUC=0.86
External: ACC=0.80 / AUC=0.87

No
CYP2C9 inhibitor?

Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set)
and tested on 2075 molecules (test set)
10-fold CV: ACC=0.78 / AUC=0.85
External: ACC=0.71 / AUC=0.81

No
CYP2D6 inhibitor?

Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set)
and tested on 1068 molecules (test set)
10-fold CV: ACC=0.79 / AUC=0.85
External: ACC=0.81 / AUC=0.87

Yes
CYP3A4 inhibitor?

Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set)
and tested on 2579 molecules (test set)
10-fold CV: ACC=0.77 / AUC=0.85
External: ACC=0.78 / AUC=0.86

No
Log Kp (skin permeation)?

Skin permeation: QSPR model implemented from
Potts RO and Guy RH. 1992 Pharm. Res.

-5.66 cm/s

Druglikeness

Lipinski?

Lipinski (Pfizer) filter: implemented from
Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev.
MW ≤ 500
MLOGP ≤ 4.15
N or O ≤ 10
NH or OH ≤ 5

0.0
Ghose?

Ghose filter: implemented from
Ghose AK. et al. 1999 J. Comb. Chem.
160 ≤ MW ≤ 480
-0.4 ≤ WLOGP ≤ 5.6
40 ≤ MR ≤ 130
20 ≤ atoms ≤ 70

None
Veber?

Veber (GSK) filter: implemented from
Veber DF. et al. 2002 J. Med. Chem.
Rotatable bonds ≤ 10
TPSA ≤ 140

0.0
Egan?

Egan (Pharmacia) filter: implemented from
Egan WJ. et al. 2000 J. Med. Chem.
WLOGP ≤ 5.88
TPSA ≤ 131.6

0.0
Muegge?

Muegge (Bayer) filter: implemented from
Muegge I. et al. 2001 J. Med. Chem.
200 ≤ MW ≤ 600
-2 ≤ XLOGP ≤ 5
TPSA ≤ 150
Num. rings ≤ 7
Num. carbon > 4
Num. heteroatoms > 1
Num. rotatable bonds ≤ 15
H-bond acc. ≤ 10
H-bond don. ≤ 5

0.0
Bioavailability Score?

Abbott Bioavailability Score: Probability of F > 10% in rat
implemented from
Martin YC. 2005 J. Med. Chem.

0.55

Medicinal Chemistry

PAINS?

Pan Assay Interference Structures: implemented from
Baell JB. & Holloway GA. 2010 J. Med. Chem.

0.0 alert
Brenk?

Structural Alert: implemented from
Brenk R. et al. 2008 ChemMedChem

0.0 alert: heavy_metal
Leadlikeness?

Leadlikeness: implemented from
Teague SJ. 1999 Angew. Chem. Int. Ed.
250 ≤ MW ≤ 350
XLOGP ≤ 3.5
Num. rotatable bonds ≤ 7

No; 1 violation:MW<1.0
Synthetic accessibility?

Synthetic accessibility score: from 1 (very easy) to 10 (very difficult)
based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties,
trained on 12'782'590 molecules and tested on 40 external molecules (r2 = 0.94)

2.2
 

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Technical Information

Categories

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