[ CAS No. 22368-21-4 ] {[proInfo.proName]}

Name: 22368-21-4|2-(3,4-Dimethoxyphenyl)-5,7-dihydroxy-6-methoxy-4H-chromen-4-one|98%
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SKU: A121685
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Quality Control of [ 22368-21-4 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 22368-21-4 ]

SDS Specification

Alternatived Products of [ 22368-21-4 ]

Product Details of [ 22368-21-4 ]

CAS No. :	22368-21-4	MDL No. :	MFCD13194819
Formula :	C₁₈H₁₆O₇	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	DRRWBCNQOKKKOL-UHFFFAOYSA-N
M.W :	344.32	Pubchem ID :	5273755
Synonyms :	NSC 122413	Chemical Name :	2-(3,4-Dimethoxyphenyl)-5,7-dihydroxy-6-methoxy-4H-chromen-4-one

Calculated chemistry of [ 22368-21-4 ]

Physicochemical Properties

Num. heavy atoms :	25
Num. arom. heavy atoms :	16
Fraction Csp3 :	0.17
Num. rotatable bonds :	4
Num. H-bond acceptors :	7.0
Num. H-bond donors :	2.0
Molar Refractivity :	91.44
TPSA :	98.36 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	Yes
CYP2D6 inhibitor :	Yes
CYP3A4 inhibitor :	Yes
Log Kp (skin permeation) :	-5.99 cm/s

Lipophilicity

Log Po/w (iLOGP) :	3.11
Log Po/w (XLOGP3) :	3.4
Log Po/w (WLOGP) :	2.9
Log Po/w (MLOGP) :	0.17
Log Po/w (SILICOS-IT) :	3.12
Consensus Log Po/w :	2.54

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	0.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-4.33
Solubility :	0.0162 mg/ml ; 0.0000472 mol/l
Class :	Moderately soluble
Log S (Ali) :	-5.14
Solubility :	0.00247 mg/ml ; 0.00000716 mol/l
Class :	Moderately soluble
Log S (SILICOS-IT) :	-5.33
Solubility :	0.00163 mg/ml ; 0.00000472 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	0.0
Synthetic accessibility :	3.39

Safety of [ 22368-21-4 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 22368-21-4 ]

* 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.

Upstream synthesis route of [ 22368-21-4 ]
Downstream synthetic route of [ 22368-21-4 ]

[ 22368-21-4 ] Synthesis Path-Upstream 1~10

1
[ 40983-99-1 ]
[ 22368-21-4 ]

Yield	Reaction Conditions	Operation in experiment
74%	With hydrogenchloride; aluminium trichloride In chloroform; acetonitrile	EXAMPLE 2 5,7-dihydroxy-3',4',6-trimethoxy flavone After 7-hydroxy-3',4',5,6-tetramethoxy flavone (4.44 g, 12.4 mmol) was suspended in 88 mL of acetonitrile and aluminum trichloride (8.27 g, 5 equivalents) was added hereto at room temperature, the reaction mixture was refluxed for 1.5 hour and the solvent was removed by evaporation under reduced pressure. To the residue was added 10percent aqueous solution of hydrochloric acid and chloroform, then the solution was refluxed until it became clear. After the solution was cooled to room temperature, the organic layer was washed with water and brine, then dried over anhydrous magnesium sulfate and the solvent of the organic layer was removed by reduced pressure. The residue was recrystallized in methanol to afford 3.18 g of the product (74percent). NMR(CDCl₃): 13.05(s,1H), 7.50(dd, J=8.6, 2.2 Hz, 1H), 7.31(d, J=2.1 Hz, 1H), 6.96(d, J=8.5 Hz, 1H), 6.59(s, 1H), 6.56(s, 1H), 6.48(br s, 1H), 4.03(s, 3H), 3.96(s, 3H), 3.95(s, 1H).
66%	With aluminum (III) chloride In acetonitrile at 90℃;	This step is a step of performing Step-9 of FIG. 3 and will be described in detail as follows.Acetonitrile (100 mL)Was suspended (3,4-dimethoxyphenyl) -7-hydroxy-5,6-dimethoxy-4H-chromen-4-one (precursor compound 9)(11 g; 0.0307 mol, 1 equiv), AlCl3 (20.3 g; 0.153 mol; 5 equiv) was added in small portions at room temperature, and the mixture was refluxed at 90 DEG C for 2 hours. The reaction was complete by TLC and the solvent was evaporated to dryness. The resulting residue was treated with aqueous HCl (10percent; 200 mL) and chloroform (200 mL) and refluxed until the reaction mixture was clear. TLC (7: 3 / PE: EtOAc; After confirming completion, the reaction mixture was cooled to room temperature and the organic phase was separated. The water phase was again extracted with DCM and the organic phase was washed with water and brine solution, dried over sodium sulfate and concentrated. The residue was applied to silica gel (60-120 mesh) column chromatography and eluted with DCM to give yellow solid(3,4-dimethoxyphenyl) -5,7-dihydroxy-6-methoxy-4H-chromen-4-one (precursor compound 10) (yield: 7.0 g; 66percent).

Reference： [1] Patent: US6025387, 2000, A,
[2] Patent: KR101871166, 2018, B1, . Location in patent: Paragraph 0137-0139
[3] Patent: US2017/239211, 2017, A1, . Location in patent: Paragraph 1/15

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[ 480-40-0 ]
[ 22368-21-4 ]