[ CAS No. 491-54-3 ] {[proInfo.proName]}

Name: 491-54-3|3,5,7-Trihydroxy-2-(4-methoxyphenyl)-4H-chromen-4-one|98%
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SKU: A125385
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Quality Control of [ 491-54-3 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 491-54-3 ]

SDS Specification

Alternatived Products of [ 491-54-3 ]

Product Details of [ 491-54-3 ]

CAS No. :	491-54-3	MDL No. :	MFCD00016771
Formula :	C₁₆H₁₂O₆	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	SQFSKOYWJBQGKQ-UHFFFAOYSA-N
M.W :	300.26	Pubchem ID :	5281666
Synonyms :	Kaempferol 4'-O-methyl ether;NSC 407294;3,5,7-Trihydroxy-4′-methoxyflavone;Kaempferol 4'-methyl ether;4'-O-Methylkaempferol;4'-Methylkaempferol	Chemical Name :	3,5,7-Trihydroxy-2-(4-methoxyphenyl)-4H-chromen-4-one

Calculated chemistry of [ 491-54-3 ]

Physicochemical Properties

Num. heavy atoms :	22
Num. arom. heavy atoms :	16
Fraction Csp3 :	0.06
Num. rotatable bonds :	2
Num. H-bond acceptors :	6.0
Num. H-bond donors :	3.0
Molar Refractivity :	80.48
TPSA :	100.13 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	Yes
CYP3A4 inhibitor :	Yes
Log Kp (skin permeation) :	-6.56 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.43
Log Po/w (XLOGP3) :	2.22
Log Po/w (WLOGP) :	2.59
Log Po/w (MLOGP) :	0.22
Log Po/w (SILICOS-IT) :	2.55
Consensus Log Po/w :	2.0

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.51
Solubility :	0.0936 mg/ml ; 0.000312 mol/l
Class :	Soluble
Log S (Ali) :	-3.96
Solubility :	0.0331 mg/ml ; 0.00011 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-4.52
Solubility :	0.00907 mg/ml ; 0.0000302 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	0.0
Synthetic accessibility :	3.16

Safety of [ 491-54-3 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 491-54-3 ]

* 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 [ 491-54-3 ]

[ 491-54-3 ] Synthesis Path-Downstream 1~68

1
[ 491-54-3 ]
[ 77-78-1 ]
[ 15486-33-6 ]
[ 15486-34-7 ]

Reference： [1]Journal of the Chemical Society,1955,p. 170,173

2
[ 491-54-3 ]
[ 77-78-1 ]
[ 16692-52-7 ]

Reference： [1]Journal of Organic Chemistry,1959,vol. 24,p. 408
[2]Phytochemistry,1981,vol. 20,p. 339 - 340

3
[ 491-54-3 ]
[ 13544-52-0 ]

Reference： [1]Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan,1932,vol. 52,p. 358,360; dtsch. Ref. S. 47
Chem.Abstr.,1932,p. 4333

4
[ 20869-95-8 ]
[ 491-54-3 ]

Reference： [1]Journal of the Chemical Society,1947,p. 122

5
[ 65982-77-6 ]
[ 794-94-5 ]
[ 491-54-3 ]

Reference： [1]Journal of the Chemical Society,1926,p. 2339

6
[ 520-18-3 ]
[ 1592-70-7 ]
[ 491-54-3 ]

Reference： [1]Phytochemistry,1980,vol. 19,p. 741 - 746

7
[ 491-54-3 ]
[ 108-24-7 ]
[ 38681-32-2 ]

Reference： [1]Phytochemistry,1981,vol. 20,p. 339 - 340
[2]Journal of the Indian Chemical Society,1985,vol. 62,p. 616 - 619
[3]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 5709 - 5712

8
[ 491-54-3 ]
[ 100-09-4 ]

Reference： [1]Phytochemistry,1981,vol. 20,p. 339 - 340

9
kaempferide 3-O-β-D-galactopyranoside [ No CAS ]
[ 491-54-3 ]

Reference： [1]Phytochemistry,1981,vol. 20,p. 339 - 340

10
4'methoxykaempferol-3-O-4α-L-rhamnopyranosyl-7-O-β-D-xylopyranoside [ No CAS ]
[ 491-54-3 ]

Reference： [1]Journal of the Indian Chemical Society,1994,vol. 71,p. 209 - 212

Yield	Reaction Conditions	Operation in experiment
		Specifically preferred are compounds selected the group of: Flavone, Baicalein, Diosmin, Kaempferide Tangeretine, 3-OH-Flavone Fisetin, Myricetin, Flavanone, ...

13
[ 491-54-3 ]
potash [ No CAS ]
[ 64-18-6 ]
[ 108-73-6 ]
[ 144-62-7 ]

Reference： [1]Chemische Berichte,1881,vol. 14,p. 2385

14
[ 491-54-3 ]
[ 7697-37-2 ]
[ 144-62-7 ]
[ 100-09-4 ]

Reference： [1]Chemische Berichte,1881,vol. 14,p. 2385

15
3-[[2-O-(6-deoxy-α-L-mannopyranosyl)-β-D-glucopyranosyl]oxy]-5,7-dihydroxy-2-(4-methoxyphenyl)-4H-1-benzopyran-4-one [ No CAS ]
[ 491-54-3 ]

Reference： [1]Phytochemistry,2000,vol. 53,p. 87 - 92

16
kaempferide 3-O-(6''-O-acetyl-4'''-O-α-methylsinapyl)neohesperidoside [ No CAS ]
[ 491-54-3 ]

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,2003,vol. 42,p. 956 - 958

17
[ 186581-53-3 ]
[ 491-54-3 ]
[ 16692-52-7 ]

Reference： [1]Journal of the Indian Chemical Society,2006,vol. 83,p. 297 - 298

18
[ 108-73-6 ]
[ 491-54-3 ]

Reference： [1]Journal of the Chemical Society,1926,p. 2339
[2]Journal of Organic Chemistry,2020,vol. 85,p. 4279 - 4288

19
[ 491-54-3 ]
[ 15486-34-7 ]

Reference： [1]Journal of the Chemical Society,1955,p. 170,173

20
[ 491-54-3 ]
[ 16692-52-7 ]

Reference： [1]Journal of the Chemical Society,1955,p. 170,173

21
[ 1258963-38-0 ]
[ 3615-41-6 ]
[ 491-54-3 ]

Reference： [1]Chemistry of Natural Compounds,2010,vol. 46,p. 205 - 208

22
[ 17633-77-1 ]
[ 491-54-3 ]
[ 1246764-75-9 ]
[ 1246764-76-0 ]
[ 1046759-43-6 ]
[ 1246764-74-8 ]

Reference： [1]European Journal of Medicinal Chemistry,2010,vol. 45,p. 4258 - 4269

23
C₃₇H₃₀O₆ [ No CAS ]
[ 491-54-3 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 5709 - 5712

24
[ 3570-69-2 ]
[ 491-54-3 ]

Yield	Reaction Conditions	Operation in experiment
55%	With potassium pyrosulfite; In ethanol; at 100℃;	General procedure: Dihydroflavonols (5, 0.3 mmol) in ethanol (2.5 ml) was added to potassium metabisulphite, (5.0 ml, 20%) and heated at 100 C (5-8 h). The reaction mixture is poured into crushed ice. The centrifuged product was purified by column (SiO2) chromatography. The purity of final products were analyzed by HPLC and NMR (Supplementary data).

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 5328 - 5330

25
[ 689260-84-2 ]
[ 491-54-3 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 5328 - 5330

26
[ 36804-11-2 ]
[ 491-54-3 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 5328 - 5330

27
4-methoxy-2',4',6'-trimethoxymethoxychalcone [ No CAS ]
[ 491-54-3 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 5328 - 5330

28
[ 123-11-5 ]
[ 491-54-3 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 5328 - 5330

29
[ 331-39-5 ]
[ 491-54-3 ]
[ 1219698-82-4 ]
[ 1219698-83-5 ]

Yield	Reaction Conditions	Operation in experiment
	Laccase DAIWA Y120; In water; at 50℃; for 0.516667h;Enzymatic reaction;	<strong>[491-54-3]Kaempferide</strong> (100 mug) and caffeic acid (100 mug) were dissolved in purified water (200 muL), and the mixture was warmed in an incubator at 50 C. for 1 minute. Laccase DAIWA Y120 (10 muL, Amano Enzyme Inc.) prepared to 5 mg/mL was added and the mixture was stirred for 1 minute. Ethanol (200 muL) was further added to quench the enzyme reaction. This reaction mixture (1 muL) was analyzed by LC/MS, and two components having a molecular weight of 478 could be confirmed in the fractions is with retention time 52.4 minutes and 54.4 minutes. UV spectrum was simultaneously measured by a photodiode array detector (see FIGS. 30 to 32). As a result of the UV spectrum analysis of each component, the absorption around 370 nm derived from ring C of kaempferide disappeared, and only the absorption around 280 nm derived from ring A and ring B was strongly detected, which confirms that the structure of (compound 29) or (compound 30) was produced. The apparatus and measurement conditions of LC/MS and photodiode array detector are shown below.LC/MS analysis apparatus:LC: Waters Alliance 2695detector: Waters 2996 Photodiode array detector (manufactured by Waters)detector: Waters Quattro micro API (manufactured by Waters) ionization method: ESILC/MS analysis conditions:column: CAPCELL PAK AQ S-3 mum, 2×250 mm (manufactured by Shiseido Co., Ltd.)gradient conditions: 0 minute (SOLUTION A/SOLUTION B=100:0), 100 minutes (SOLUTION A/SOLUTION B=0:100), injection volume: 1 muL, flow rate: 0.2 mL/minute, solvent: SOLUTION A solution of 0.05% trifluoroacetic acid and 10% acetonitrile in water, SOLUTION B solution of 0.05% trifluoroacetic acid and 80% acetonitrile in water

Reference： [1]Patent: US2011/237533,2011,A1 .Location in patent: Page/Page column 27

30
[ 491-54-3 ]
[ 554453-86-0 ]

Reference： [1]Chemistry of Natural Compounds,2013,vol. 49,p. 108 - 109
Khim. Prir. Soedin.,2012,vol. 49,p. 96,1

31
7-(benzyloxy)-3,5-dihydroxy-2-(4-methoxyphenyl)-4H-chromen-4-one [ No CAS ]
[ 491-54-3 ]

Yield	Reaction Conditions	Operation in experiment
93%	With palladium 10% on activated carbon; hydrogen; In methanol; ethyl acetate; at 20℃; for 5h;	A mixture of 17(410 mg, 1.05 mmol), 10% Pd/C (45 mg), MeOH (27 mL) and EtOAc (9 mL) wasstirred at room temperature under a hydrogen balloon for 5 h. The mixture wasfiltered off through celite eluting with EtOAc (10 mL). The filtrate wasconcentrated to give the crude product, whichwas crystallized fromacetone/petroleum ether (1:2) to yield 18(293 mg, 93%) as yellowcrystals, mp:177-178C. IR (cm-1): 3445, 3291, 2925, 2854, 1615,1510, 1374, 1310, 1253, 1172. 1H NMR (400 MHz, DMSO-d6): delta = 12.44 (s, 1H, OH-5), 10.83 (s, 1H, OH-7), 9.53 (s, 1H,OH-3), 8.14 (d, J= 9.1 Hz, 2H, H-2?,6?), 7.11 (d, J= 9.1 Hz, 2H,H-3?,5?), 6.46 (d, J= 2.0 Hz, 1H, H-8), 6.20 (d, J= 2.0 Hz, 1H,H-6), 3.84 (s, 3H, OCH3-4?).13CNMR (150 MHz, DMSO-d6): delta = 176.01(C-4), 164.00(C-7),160.73(C-5), 160.50(C-4?), 156.25(C-9), 146.28(C-2), 136.06(C-3),129.34(C-2?,6?), 123.27(C-1?), 114.06(C-3?,5?), 103.10(C-10), 98.25(C-6),93.53(C-8), 55.37(OCH3-4?). ESI-HRMS: 299.0560 [M-H]-(calcd. for C16H11O6: 299.0561).

Reference： [1]Beilstein Journal of Organic Chemistry,2015,vol. 11,p. 288 - 293

32
[ 16274-11-6 ]
[ 491-54-3 ]

Reference： [1]Beilstein Journal of Organic Chemistry,2015,vol. 11,p. 288 - 293

33
[ 520-18-3 ]
[ 491-54-3 ]

Reference： [1]Beilstein Journal of Organic Chemistry,2015,vol. 11,p. 288 - 293

34
2-(4-acetoxyphenyl)-7-(benzyloxy)-4-oxo-4H-chromene-3,5-diyl diacetate [ No CAS ]
[ 491-54-3 ]

Reference： [1]Beilstein Journal of Organic Chemistry,2015,vol. 11,p. 288 - 293

35
[ 100-09-4 ]
[ 491-54-3 ]