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Quality Control of [ 85614-43-3 ] Purity: 98% SDS Specification

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Product Details of [ 85614-43-3 ]

CAS No. :	85614-43-3
Formula :	C₁₂H₁₄O₄
M.W :	222.24
SMILES Code :	COC(=O)C1=C(O)C(OC)=CC(CC=C)=C1
MDL No. :	MFCD04038819
InChI Key :	LYSUGZLJKRSLHM-UHFFFAOYSA-N
Pubchem ID :	3020842

Safety of [ 85614-43-3 ]

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

Computational Chemistry of [ 85614-43-3 ] Show Less

Physicochemical Properties

Num. heavy atoms	16
Num. arom. heavy atoms	6
Fraction Csp3	0.25
Num. rotatable bonds	5
Num. H-bond acceptors	4.0
Num. H-bond donors	1.0
Molar Refractivity	60.34
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	55.76 ?2

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.17
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	3.01
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.92
Log P_o/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.	1.85
Log P_o/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	2.47
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.28

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-3.06
Solubility	0.193 mg/ml ; 0.000868 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.	-3.85
Solubility	0.0317 mg/ml ; 0.000143 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	-2.88
Solubility	0.29 mg/ml ; 0.0013 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	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	No
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	No
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.	-5.52 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	1.0 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)	2.32

Application In Synthesis of [ 85614-43-3 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 85614-43-3 ]

[ 85614-43-3 ] Synthesis Path-Downstream 1~31

1
[ 85614-43-3 ]
[ 2216-99-1 ]

Yield	Reaction Conditions	Operation in experiment
98%		110 g of <strong>[85614-43-3]methyl 5-allyl-3-methoxysalicylate</strong> (97% pure Aldrich grade) was transferred into a 2000ml 3-necked round bottom flask (RBF) fitted with an overhead stirrer and a reflux condenser. To this aqueous NaOH solution (44 g of NaOH in 1000 ml water) was added and the resultant mixture was refluxed with stirring (bath temp. 110C) for 2-3 h. Progress of the reaction was monitored by quenching aliquot sample with dilute hydrochloric acid followed by extraction with solvent (ethylene dichloride (EDC) or ether) and analyzing by HPLC (area %) for the conversion of ester to acid. Having ensured the complete conversion by HPLC, cool the reaction mixture to room temperature (25 C) and add the same drop wise into a beaker containing dilute HC1 (140 ml 35% HC1 in 350 ml water) with stirring. The acid (product) precipitates as a solid and the resultant slurry was stirred for about an hour, then filtered, washed with DM water till chloride free and dried (110 C for 8h, moisture ~<1%). Yield: 101 g (98%), purity: 99.7% (HPLC area %).
	With sodium hydroxide; In methanol; water; at 50℃; for 2h;	Methyl 5-allyl-3-methoxysalicylate (manufactured by Tokyo Kasei Kogyo Co., Ltd.)10 parts,200 parts of water and 100 parts of methanol, followed by the addition of 1.8 parts of sodium hydroxide and heating at 50 DEG C for 2 hours.After cooling, the reaction solution was added to 200 parts of ice water, stirred for 1 hour, and then hydrochloric acid was added until the pH became 2. The resulting precipitate was filtered and washed with 200 parts of ion-exchanged water to obtain 8.5 parts of a compound represented by the formula (BC-14-A).

References: [1]Patent: WO2015/15445,2015,A2 .Location in patent: Paragraph 0134.
[2]Justus Liebigs Annalen der Chemie,1919,vol. 418,p. 102.
[3]Patent: KR2015/41745,2015,A .Location in patent: Paragraph 0359-0360.

2
[ 85614-43-3 ]
[ 857599-38-3 ]

References: [1]Chemische Berichte,1940,vol. 73,p. 1369,1372.

3
[ 85614-43-3 ]
2-benzyloxy-3-methoxy-5-propyl-benzoic acid [ No CAS ]

References: [1]Chemische Berichte,1952,vol. 85,p. 86,88.

4
[ 96619-89-5 ]
[ 85614-43-3 ]

Yield	Reaction Conditions	Operation in experiment
8.6 g	at 200℃; for 2h;	Under a nitrogen atmosphere, 10.0 g of methyl 2-hydroxy-3-methoxybenzoate (3) was added to a three-necked flask.4.2 g of sodium hydroxide, 100 ml of acetone was added as a solvent, and the oil bath was heated and refluxed for 60 minutes.Then, 11.3 ml of allyl bromide was added dropwise, and the reaction was continued for 10 hours. After the reaction was completed, the temperature was lowered to room temperature.Filtration, evaporation of the solvent to obtain an oil (4), warming to 200 C, reaction for 2 hours, cooling,Purification by cyclohexane:acetone = 1:1 to give the white solid solid methyl 2-hydroxy-3-methoxy-5-allylbenzoate (5) 8.6 g,The purity is 96.8%.

References: [1]Journal of Medicinal Chemistry,1991,vol. 34,p. 1612 - 1624.
[2]Justus Liebigs Annalen der Chemie,1919,vol. 418,p. 102.
[3]Patent: CN109836351,2019,A .Location in patent: Paragraph 0017-0018; 0020-0021.

5
[ 85614-43-3 ]
[ 62-53-3 ]
[ 97-53-0 ]

References: [1]Justus Liebigs Annalen der Chemie,1919,vol. 418,p. 102.

6
[ 85614-43-3 ]
[ 74-88-4 ]
[ 133129-47-2 ]

References: [1]Journal of Medicinal Chemistry,1991,vol. 34,p. 1612 - 1624.
[2]Bioorganic and Medicinal Chemistry Letters,2008,vol. 18,p. 4467 - 4469.

7
[ 85614-43-3 ]
[ 110057-59-5 ]