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[ CAS No. 520-34-3 ] {[proInfo.proName]}

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Cat. No.: {[proInfo.prAm]}
Chemical Structure| 520-34-3
Chemical Structure| 520-34-3
Structure of 520-34-3 * Storage: {[proInfo.prStorage]}
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Product Details of [ 520-34-3 ]

CAS No. :520-34-3 MDL No. :MFCD00017425
Formula : C16H12O6 Boiling Point : -
Linear Structure Formula :- InChI Key :MBNGWHIJMBWFHU-UHFFFAOYSA-N
M.W : 300.26 Pubchem ID :5281612
Synonyms :
Diosmetol;Luteolin 4-methyl ether;Luteolin 4'-methyl ether;HSDB 8101;Luteolin 4'-methyl ester

Calculated chemistry of [ 520-34-3 ]

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 Ų

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) : -5.93 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.47
Log Po/w (XLOGP3) : 3.1
Log Po/w (WLOGP) : 2.59
Log Po/w (MLOGP) : 0.22
Log Po/w (SILICOS-IT) : 2.55
Consensus Log Po/w : 2.19

Druglikeness

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

Water Solubility

Log S (ESOL) : -4.06
Solubility : 0.0261 mg/ml ; 0.0000869 mol/l
Class : Moderately soluble
Log S (Ali) : -4.87
Solubility : 0.00404 mg/ml ; 0.0000135 mol/l
Class : Moderately 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 : 3.05

Safety of [ 520-34-3 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 520-34-3 ]

* 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 [ 520-34-3 ]

[ 520-34-3 ] Synthesis Path-Downstream   1~87

  • 1
  • [ 520-34-3 ]
  • [ 74-88-4 ]
  • [ 23367-08-0 ]
  • 2
  • [ 520-33-2 ]
  • [ 520-34-3 ]
YieldReaction ConditionsOperation in experiment
60% With pyridine; iodine; at 95℃; for 5h; General procedure: Apigenin: A solution of naringenin (5.0 g, 18 mmol) and iodine (5.0 g,19 mmol) in pyridine (50 mL) was heated to 95 C for 5 h. The mixturewas poured into ice water. The resulting precipitate was filtered,and then washed with water, dilute hydrochloric acid and saturatedsodium thiosulfate. Recrystallisation of the dried residue from ethanolafforded apigenin: 3.20 g; 66%
  • 3
  • [ 102593-81-7 ]
  • [ 520-34-3 ]
  • 4
  • [ 102548-67-4 ]
  • [ 520-34-3 ]
  • 5
  • [ 1120-71-4 ]
  • [ 520-34-3 ]
  • [ 70412-86-1 ]
  • 7
  • [ 748-62-9 ]
  • [ 520-34-3 ]
  • 8
  • [ 72629-61-9 ]
  • [ 520-34-3 ]
  • [ 32174-62-2 ]
  • [ 10544-05-5 ]
  • [ 33554-52-8 ]
  • 9
  • [ 491-70-3 ]
  • [ 520-34-3 ]
  • [ 491-71-4 ]
  • [ 25739-41-7 ]
  • [ 32174-62-2 ]
  • 10
  • [ 520-34-3 ]
  • [ 77-78-1 ]
  • [ 29080-58-8 ]
YieldReaction ConditionsOperation in experiment
69% With potassium carbonate; In acetone; at 60 - 65℃; for 8h;Inert atmosphere; To a mixture of <strong>[520-34-3]diosmetin</strong> (2 g, 6.7 mmol) and K2CO3 (3.72 g, 26.6 mmol) in acetone 10 mL was added (CH3)2SO4 (2.2 mL, 24.3 mmol), and the mixture was stirred under nitrogen for 8 h at 60-65 C. The mixture was cooled to room temperature and poured into cold water (200 mL). The resulting precipitate was filtered and washed successively with saturated NaHCO3 (aq) and water, and then evaporated to dryness. The crude solid was chromatographed on silica gel using petroleum ether/ethyl acetate (3 : 1) as eluent to afford a yellow solid 1.52 g (69%); m.p.166-169 C (lit.17 m.p. 169 C);
  • 12
  • [ 3162-05-8 ]
  • [ 520-34-3 ]
  • 13
  • [ 141360-86-3 ]
  • [ 520-34-3 ]
  • 14
  • [ 520-27-4 ]
  • [ 520-34-3 ]
YieldReaction ConditionsOperation in experiment
85% With sulfuric acid; water; at 20℃; for 0.166667h; General procedure: Sulfuric acid (2.0mL, 0.037mmol) was added dropwise to a beaker (100 mL) containing scutellarin (50 mg, 0.11 mmol). It was shaken or agitated by ultrasound agitated to dissolve the substrate in the acid at room temperature. Water (2.0 mL) was then added carefully dropwise. When the evolution of heat ceased (in 10 minutes), the mixture was added to water (15 mL) in one portion with stirring with a glass rod. The yellow crystals that were deposited were collected by suction filtration and washed by water (5 mL). In most cases, such products were pure enough for direct use. Moreover, it could be further purified by recrystallisation from aqueous methanol (70%, v/v) or column chromatography on silica gel (eluent:ethyl acetate/formic acid/water=100/4/3, v/v/v, Rfs of SCU and SCUE were 0.1 and 0.8 on silica gel GF254 respectively). Light yellow crystals were obtained after recrystallisation (28.5mg, 93% yield); m.p. 285-287C (>300C)27. IR (KBr, cm-1): numax 3442, 3331, 3098, 1671, 1619, 1587, 1509. 1H NMR (500MHz, DMSO-d6): delta 12.80 (s, 1H, 5-OH), 10.48 (s, 1H, 7-OH), 10.33 (s, 1H, 4?-OH), 8.75 (s, 1H, 6-OH), 7.92 (d, 2H, J=8.6Hz, C2?, C6?-H), 6.92 (d, 2H, J=8.6Hz, C3?, C5?-H), 6.75 (s, 1H, C3-H), 6.58 (s, 1H, C8-H). HR-ESI-MS (m/z): 309.0363 for [M+Na]+, calcd 309.0370.
100 kg With sodium hydroxide; at 100℃; for 0.666667h;Large scale; Add to the new dioxin obtained in step 1)1500 kg of sodium hydroxide solution with a mass concentration of 32%, continue to raise the temperature to 100 C for 40 minutes, and after monitoring the content of neodoxime to 2% or less in the liquid phase, add hydrochloric acid to the reaction solution to neutralize the pH to 6 7, then cool down to 15 C ~ 25 C to cool, centrifuge, collect the precipitate, and wash the precipitate,Get 120 kg of geranyl lignin crude; Step 3) Preparation of geranyl ligninAdd 20 times volume of ethanol with a mass concentration of 80% to 120 kg of crude geranin, and heat to reflux.Solution, then add 12 kg of activated carbon for decolorization. After the decolorization is completed, the activated carbon is removed by filtration, the filtrate is collected, and the filtrate is concentrated under reduced pressure to 1/3 of the original volume using a double-effect concentrator. The solution is allowed to stand, cooled and crystallized, and centrifuged to obtain geranium lignin. Boutique 100 kg.
  • 16
  • [ 520-34-3 ]
  • [ 106-89-8 ]
  • 3',7-di-O-(2,3-epoxypropyl)diosmetin [ No CAS ]
  • 19
  • meso-8,10-di-n-propyllobelidiol [ No CAS ]
  • [ 520-34-3 ]
  • 20
  • [ 520-34-3 ]
  • [ 105-39-5 ]
  • [ 198886-53-2 ]
  • 21
  • [ 520-34-3 ]
  • [ 105-39-5 ]
  • [ 123580-49-4 ]
  • 22
  • [ 520-34-3 ]
  • [4-(2,3,4-trimethoxy-benzyl)-piperazin-1-yl]-acetyl chloride [ No CAS ]
  • 5,3'-dihydroxy-4'-methoxy-7-<4-<(2,3,4-trimethoxyphenyl)methyl>piperazin-1-ylcarbonylmethoxy>flavone [ No CAS ]
  • 23
  • [ 520-34-3 ]
  • [4-(2,3,4-trimethoxy-benzyl)-piperazin-1-yl]-acetyl chloride [ No CAS ]
  • 7,3'-bis<4-<(2,3,4-trimethoxyphenyl)methyl>piperazin-1-ylcarbonylmethoxy>-5-hydroxy-4'-methoxyflavone [ No CAS ]
  • 25
  • [ 520-34-3 ]
  • KOH-solution [ No CAS ]
  • [ 108-73-6 ]
  • 26
  • [ 520-34-3 ]
  • [ 10034-85-2 ]
  • [ 491-70-3 ]
  • 29
  • 2.4.6-triacetoxy-ω-<4-methoxy-3-acetoxy-benzyliden>-acetophenone [ No CAS ]
  • [ 520-34-3 ]
  • 31
  • tri-<i>O</i>-acetyl-diosmetin [ No CAS ]
  • [ 520-34-3 ]
  • 32
  • tri-<i>O</i>-acetyl-disometin [ No CAS ]
  • [ 520-34-3 ]
  • 34
  • [ 35110-20-4 ]
  • [ 520-34-3 ]
  • 35
  • [ 520-34-3 ]
  • 6,8-diododiosmetin [ No CAS ]
  • 36
  • [ 520-34-3 ]
  • [ 100-44-7 ]
  • [ 172805-73-1 ]
  • [ 159355-57-4 ]
  • 37
  • [ 520-34-3 ]
  • [ 771481-08-4 ]
  • 38
  • [ 520-34-3 ]
  • [ 50848-66-3 ]
  • 39
  • [ 520-34-3 ]
  • [ 480-44-4 ]
  • 40
  • [ 520-34-3 ]
  • [ 5128-44-9 ]
  • 41
  • [ 520-34-3 ]
  • 3',7-bis-O-[2-(1-piperidino)ethyl]diosmetin [ No CAS ]
  • 42
  • [ 520-34-3 ]
  • 3',7-bis-O-[2-(4-methyl-1-piperazinyl)ethyl]diosmetin [ No CAS ]
  • 43
  • [ 520-34-3 ]
  • 3',7-bis-O-[2-(1-piperazinyl)ethyl]diosmetin [ No CAS ]
  • 44
  • [ 520-34-3 ]
  • 3',7-bis-O-[2-(2-benzoxazolylthio)ethyl]diosmetin [ No CAS ]
  • 45
  • [ 520-34-3 ]
  • 3',7-bis-O-[2-(2-benzothiazolylthio)ethyl]diosmetin [ No CAS ]
  • 46
  • [ 520-34-3 ]
  • 3',7-bis-O-[2-(2-benzimidazolylthio)ethyl]diosmetin [ No CAS ]
  • 47
  • [ 520-34-3 ]
  • 3',7-bis-O-[2-[4-(2-benzothiazolyl)-1-piperidinyl]ethyl]diosmetin [ No CAS ]
  • 48
  • [ 520-34-3 ]
  • 7,3'-dihydroxy-4'-methoxy-5-<4-<(2,3,4-trimethoxyphenyl)methyl>piperazin-1-ylcarbonylmethoxy>flavone [ No CAS ]
  • 49
  • [ 520-34-3 ]
  • 3'-<<4-(2-chlorophenyl)methyl>piperazinyl-1-ylcarbonylmethoxy>-7-(ethoxycarbonylmethoxy)-5-hydroxy-4'-methoxyflavone [ No CAS ]
  • 50
  • [ 520-34-3 ]
  • [2-(3-[4-(3,4-dimethoxy-benzyl)-piperazin-1-yl]-acetoxy}-4-methoxy-phenyl)-5-hydroxy-4-oxo-4<i>H</i>-chromen-7-yloxy]-acetic acid ethyl ester [ No CAS ]
  • 51
  • [ 520-34-3 ]
  • [5-hydroxy-2-(4-methoxy-3-[4-(2,3,4-trimethoxy-benzyl)-piperazin-1-yl]-acetoxy}-phenyl)-4-oxo-4<i>H</i>-chromen-7-yloxy]-acetic acid ethyl ester [ No CAS ]
  • 52
  • [ 520-34-3 ]
  • [5-hydroxy-2-(4-methoxy-3-[4-(3,4,5-trimethoxy-benzyl)-piperazin-1-yl]-acetoxy}-phenyl)-4-oxo-4<i>H</i>-chromen-7-yloxy]-acetic acid ethyl ester [ No CAS ]
  • 53
  • [ 520-34-3 ]
  • 7,3'-bis(benzyloxy)-4'-methoxy-5-<4-<(2,3,4-trimethoxyphenyl)methyl>piperazin-1-ylcarbonylmethoxy>flavone [ No CAS ]
  • 54
  • [ 520-34-3 ]
  • [4-(2,3,4-trimethoxy-benzyl)-piperazin-1-yl]-acetic acid 7-ethoxycarbonylmethoxy-2-(3-ethoxycarbonylmethoxy-4-methoxy-phenyl)-4-oxo-4<i>H</i>-chromen-5-yl ester [ No CAS ]
  • 58
  • [ 520-34-3 ]
  • 3',7-di-O-<2-hydroxy-3-(isopropylamino)propyl>diosmetin [ No CAS ]
  • 61
  • [ 6702-50-7 ]
  • [ 520-34-3 ]
  • 62
  • [ 645-08-9 ]
  • [ 520-34-3 ]
  • 63
  • [ 58452-00-9 ]
  • [ 520-34-3 ]
  • 64
  • [ 57535-57-6 ]
  • [ 520-34-3 ]
  • 65
  • [ 59171-19-6 ]
  • [ 520-34-3 ]
  • 66
  • [ 93-07-2 ]
  • [ 520-34-3 ]
  • 67
  • [ 6346-05-0 ]
  • [ 520-34-3 ]
  • 69
  • [ 6100-74-9 ]
  • [ 520-34-3 ]
  • 70
  • [ 23428-77-5 ]
  • [ 520-34-3 ]
  • 71
  • [ 77513-51-0 ]
  • [ 520-34-3 ]
  • 72
  • [ 39548-89-5 ]
  • [ 520-34-3 ]
YieldReaction ConditionsOperation in experiment
EXAMPLE 28 3',5,7-trihydroxy-4'-methoxy flavone 3',7-dibenzyloxy-4',5-dimethoxy flavone was obtained by the same process of the steps 3) and 4) of the Example 1 using 4-benzyloxy-6-methoxy-2-hydroxy acetophenone as a starting material, and therefrom 3',5,7-trihydroxy-4'-methoxy flavone was obtained by the process of the following step 3).
  • 73
  • [ 520-34-3 ]
  • [ 100-39-0 ]
  • [ 172805-73-1 ]
  • 74
  • [ 1458-98-6 ]
  • [ 520-34-3 ]
  • [ 1188911-04-7 ]
YieldReaction ConditionsOperation in experiment
EXAMPLE 1; 6,8,2'-Tris(isobut-2-en-1-yl)<strong>[520-34-3]diosmetin</strong> Step A: 2-{4-Methoxy-3-[(isobut-2-en-1-yl)oxy]phenyl}-5,7-bis[(isobut-2-en-1-yl)oxy]-4H-chromen-4-oneTo 30 g of <strong>[520-34-3]diosmetin</strong> there are added 69.3 g of potassium carbonate and 450 ml of acetone. The mixture is heated at reflux for 4 hours 30 minutes and then returned to ambient temperature; 54 g of methallyl bromide are then added. The reaction mixture is then heated at reflux overnight and then returned to ambient temperature and filtered. The filter cake is rinsed with acetone and then the filtrate is evaporated to yield a residue which is recrystallised from toluene to yield the title compound.
  • 75
  • [ 520-34-3 ]
  • [ 1217077-67-2 ]
  • [ 1217077-51-4 ]
  • 76
  • [ 520-34-3 ]
  • [ 1217077-67-2 ]
  • [ 1217077-51-4 ]
  • [ 1217077-54-7 ]
  • 77
  • [ 520-34-3 ]
  • [ 100-44-7 ]
  • [ 159355-57-4 ]
  • 78
  • [ 520-34-3 ]
  • diosmetin 3',7-O-disulfate [ No CAS ]
  • 79
  • [ 520-34-3 ]
  • [ 1245697-26-0 ]
  • diosmetin-7-O-glucuronide [ No CAS ]
  • 80
  • diosmetin 7-O-β-L-arabinofuranosyl-(1→2)-β-D-apiofuranoside [ No CAS ]
  • [ 520-34-3 ]
  • [ 20074-49-1 ]
  • [ 20230-73-3 ]
  • 81
  • 2'-hydroxy-4',6'-bis[(2-methoxyethoxy)methoxy]acetophenone [ No CAS ]
  • [ 520-34-3 ]
  • 82
  • [ 1456788-15-0 ]
  • [ 520-34-3 ]
  • 83
  • [ 1456788-18-3 ]
  • [ 520-34-3 ]
YieldReaction ConditionsOperation in experiment
89% With hydrogenchloride; In tetrahydrofuran; water; at 20℃; for 3h;Inert atmosphere; General procedure: A diluted solution of hydrochloric acid (20 %, 10 mL) was added to a suspension of the appropriated polyalkoxyflavones 10b-d (0.27 mmol) in tetrahydrofuran (5 mL). The reaction was stirred under nitrogen at room temperature for 3 h. After this period the reaction was poured into ice (100 g) and water (50 mL). The solid so obtained was filtered, washed abundantly with water (150 mL) and diethyl ether (50 mL) affording the expected 5,7-dihydroxyflavones 4f-h as light yellow solids in good yields: 4f, 90%, 73mg; 4g, 89%, 70mg; 4h, 86%, 73mg.
  • 85
  • quercetin-4'-methoxy 3-O-di-(L-rhamnopyranosyl)-(1'''→2",1''''→6")-β-D-glucopyranoside [ No CAS ]
  • [ 3615-41-6 ]
  • [ 50-99-7 ]
  • [ 520-34-3 ]
  • 86
  • 4,6-bis(methoxymethyl)-2-(3-acetoxy-4-methoxybenzoyloxy)acetophenone [ No CAS ]
  • [ 520-34-3 ]
YieldReaction ConditionsOperation in experiment
55% General procedure: To the esters 3 (1 mmol) in dry pyridine (1 ml) at 50 C,powdered KOH (2 mmol) was added and reaction mixture was stirred vigorously for 20 min. The reaction mass was cooled, added to aqueous acetic acid (20 ml, 10%) and stirred for 30 min. It was extracted with diethyl ether (25 mlx 2) and washed with water (10 ml x 2), dried over anhydrous Na2SO4. On removal of solvent, diketones (containing some enol forms) were obtained as yellow solid products which gave green ferric reaction and were soluble in aq.NaOH (deep yellow solution). Compounds were identified by IR and UV spectral measurements (see Table S1 in supplementary information). The diketone/enol mixtures (200mg, without purification) were taken in methanolic HCl (20ml, 10%) and refluxed for 1-2 h till the completion of reaction(monitored by TLC solvent system, toluene 50: ethylacetate50: formic acid 10). Methanol was removed and reaction mass was poured into ice-water mixture, stirred for30 min, centrifuged; the separated flavones were purified through column chromatography using SiO2 and eluted in 2-3% methanol in chloroform. Compound 4 were crystallized from mixtures of chloroform/methanol. Yields, melting points and spectral properties are given below. Compounds were characterized by 1H NMR, UV and IR data.
  • 87
  • 1-(2-Hydroxy-4,6-bis(methoxymethyl)phenyl)ethanone [ No CAS ]
  • [ 90798-12-2 ]
  • [ 520-34-3 ]
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