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[ CAS No. 520-27-4 ] {[proInfo.proName]}

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Chemical Structure| 520-27-4
Chemical Structure| 520-27-4
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Quality Control of [ 520-27-4 ]

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Product Details of [ 520-27-4 ]

CAS No. :520-27-4 MDL No. :MFCD00009772
Formula : C28H32O15 Boiling Point : -
Linear Structure Formula :- InChI Key :GZSOSUNBTXMUFQ-YFAPSIMESA-N
M.W : 608.54 Pubchem ID :5281613
Synonyms :
3’,5,7-Trihydroxy-4’-methoxyflavone 7-rutinoside
Chemical Name :5-Hydroxy-2-(3-hydroxy-4-methoxyphenyl)-7-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-((((2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)methyl)tetrahydro-2H-pyran-2-yl)oxy)-4H-chromen-4-one

Calculated chemistry of [ 520-27-4 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 43
Num. arom. heavy atoms : 16
Fraction Csp3 : 0.46
Num. rotatable bonds : 7
Num. H-bond acceptors : 15.0
Num. H-bond donors : 8.0
Molar Refractivity : 143.82
TPSA : 238.2 ?2

Pharmacokinetics

GI absorption : Low
BBB permeant : No
P-gp substrate : Yes
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -9.91 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.66
Log Po/w (XLOGP3) : 0.14
Log Po/w (WLOGP) : -1.09
Log Po/w (MLOGP) : -3.23
Log Po/w (SILICOS-IT) : -1.08
Consensus Log Po/w : -0.52

Druglikeness

Lipinski : 3.0
Ghose : None
Veber : 1.0
Egan : 1.0
Muegge : 4.0
Bioavailability Score : 0.17

Water Solubility

Log S (ESOL) : -3.51
Solubility : 0.186 mg/ml ; 0.000306 mol/l
Class : Soluble
Log S (Ali) : -4.7
Solubility : 0.0122 mg/ml ; 0.00002 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -1.57
Solubility : 16.5 mg/ml ; 0.027 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 6.48

Safety of [ 520-27-4 ]

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 [ 520-27-4 ]

* 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.

  • Downstream synthetic route of [ 520-27-4 ]

[ 520-27-4 ] Synthesis Path-Downstream   1~12

  • 1
  • [ 520-26-3 ]
  • [ 520-27-4 ]
YieldReaction ConditionsOperation in experiment
85.7% With morpholine; iodine; at 40 - 70℃;Large scale; Green chemistry; In 20L reaction kettle, add hesperidin 2 kg, iodine 0.92 kg, then add morpholine 12L. Start stirring and elevating temperature. When the temperature rises to 40 deg.C, sample is completely dissolved, At 45 deg.C ± 5 deg.C maintain temperature for 0.5 hours.Then, increase the temperature to 70 deg.C ± 5 deg.C and maintain the temperature and stir for 1.5-3 hours (HPLC monitoring hesperdin completely after transformation as the end point of the reaction). Recovery solvent to reactant into a viscous, adding 12L purified water, stirring, the material after being homogenized, the hydraulic the reaction buffer tank, adding hydrochloric acid adjusting pH=5-7 to crystallization, filtration, filter cake and filtrate, the filtrate pH=2 adjusted by adding hydrochloric acid, slowly adding 30% hydrogen peroxide 0.41 kg, filter, recovery elemental iodine. The filter cake is washed with a large amount of water washing, diosmin mode crude product obtained. Dissolving the purified water is added to the purification tank 12L and 0.39 kg sodium hydroxide, stir until completely dissolved after diosmin mode crude product into the continue to stir until completely dissolved, slowly adding at 20L acetonitrile, the solid is separated out, filtering, takes filters cake (diosmin mode sodium salt purity is of 99.27%), again dissolving the purified water is added to the purification tank 30L, then add and stir the filter cake to be completely dissolved, slowly dilute hydrochloric acid in this case adjusting pH=5-7, a large number of solid precipitation, filtration, the filter cake is washed with a large amount of purified water washing 1 hours, collecting filter cake, is put into the 80 C ± 5 C blast drying, crushing, diosmin mode the finished product to 1.69 kg, the purity is 99.44%, the yield is 85.7%, to the solvent recovery rate 80.1%, iodine recovery rate 89.6%, residual solvent, -related impurities are standard.
With pyridine; iodine; sodium hydroxide; at 95 - 105℃;Product distribution / selectivity; 100 gm of hesperidin , 700 ml of recovered pyridine, 9.8 gm of sodium hydroxide and 45.6 gm of iodine were charged in 2 liter clean glass assembly . The resulting solution was heated to 95-1050C for 9 - 10 hrs. Reaction was monitored by HPLC. Pyridine was recovered completely by distillation. Charged methanol to the resulting solid, the reaction mass was heated to reflux and filtered at room temperature. The solid obtained was treated with sodium thiosulfate solution and 900 ml, 5% aqueous NaOH solution. pH 2-4 was adjusted with cone, sulfuric acid. Reaction mass was filtered to obtain crude diosmin. Crude diosmin obtained was 80 - 86 gm. Purity was 98.6 %.
13.1 g Take an amount of 95% hesperidin 20g (previously 90 dried 3-4h), DMSO50ml dissolved by heating, the other to take 3gKBH4, graded by adding, to the reduction of hesperidin naringin type flavan-4- alcohol completely (approximately overnight , UV monitor, under alkaline conditions scans at no absorption peak at 360nm).Slowly adding 5ml of concentrated sulfuric acid (2ml particularly slow first, the solution became light red), mix well (solution becomes light red) was added slowly added anhydrous n-amyl alcohol 120ml, precipitation sink to the bottom, still 30min, poured out positive amyl alcohol solution was added to the precipitate in anhydrous n-amyl alcohol 20ml, stirring rapidly pinching solution, n-amyl alcohol was decanted, treated twice with the law, anhydrous pyridine 40ml, by adding iodine 8.3g, and stir until dissolved, no calcium sulfate 5g, stir, sealed in a water bath at 55 96h after continuous reaction.Activated carbon was added 5.0, add water 500ml, stirring slowly adding phosphoric acid modulation pH5, filtration, the filtrate was adsorbed by 300gD101 macroporous resin, 500ml water to remove pyridine, iodine ions and other impurities, and then 0.1% 0.5% phosphoric acid vitamin C400ml further elution remove residual iodine, pyridine and other impurities, washed with water 300ml, 2000ml eluted with 60% ethanol, recovering ethanol under reduced pressure.After recovery of ethanol was combined with activated charcoal 2g, mixing, filtration, water was recovered under reduced pressure to dryness to obtain Diosmetinidin-7-O-rutinoside, orange powder 13.1 g.
93 kg With bromine; iodine; In N,N-dimethyl-formamide; at 90 - 120℃;Large scale; in a 500kg of reactor, added 300.0kg of DMF, slowly added 100. 0kg of hesperidin, then added iodine1.0~5.0kg and bromine 1.0~3.0kg, while stirring the reaction was slowly heated to 90~120 C and at this temperature keep the reaction for 12~16h. The content of diosmin was detected by the sample. When the content of hesperidin was less than 1.0% then stop the reaction. Filtration, the filtrate at 80 ~ 95 C and under the vacuum is - (0.05 ~ .07) Mpa carried out recovery of solvent, to obtain creamy diosmin . in the paste creamy diosmin added 1200kg of purified water, stirred properly , stir, heated up to 40 ~ 70 C and maintain this temperature for 30 ~ 60min, Pressure filtration and wash until the outflow of water is clear. The filter cake dried in the drying room to moisture 8 ~ 15% to obtain crude product 108kg. The crude product was put into the reactor, added 864kg, 648kg and 432kg of 85% ethanol respectively, and then adding 400kg of iodine removing agent, stirring and refluxing for 60min, 40min and 30min respectively. Pressure filtration and wash until the outflow of water is clear. The filter cake was put into a reaction kettle, 700 kg of purified water, stirred properly until became thin paste, with hydrochloric acid, sulfuric acid or acetic acid PH as adjusted to 5, boiled for 40min, Pressure filtration, washing to the outflow of water until was neutral, filter cake was flash Dried to obtain 93 kg of the dried product, then granulated with a micropowder machine to obtain the diosmin according to EU EP 8.0.
With pyridine; iodine; at 100℃; for 12h;Large scale; 300 kg of liquid phase content of 95%New hesperidin, 1800 kg pyridine, 240 kg iodine into 3000 litersIn the kettle, the temperature is raised to 100 C for 12 hours, the liquid phase monitors the new hesperidin content to less than 2%, and the pyridine is recovered under reduced pressure to no liquid.After the body is steamed, the new odisamine is obtained

  • 2
  • [ 69081-76-1 ]
  • [ 520-27-4 ]
  • 3
  • hesperidin octaacetate [ No CAS ]
  • [ 520-27-4 ]
  • 4
  • [ 108-24-7 ]
  • [ 520-27-4 ]
  • diosmetin 7-rutinoside octaacetate [ No CAS ]
  • 5
  • [ 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.
  • 6
  • [ 520-27-4 ]
  • [ 107-07-3 ]
  • [ 80604-68-8 ]
YieldReaction ConditionsOperation in experiment
With triethylamine; In methanol; under 0.45 - 0.5 Torr;Large scale; The measurement of accurate 240.0kg methanol vacuum into the reactor, from the reactor mouth slowly added to the Austen Siming 60.0kg, triethylamine 1.0kg, the measurement of accurate 2-chloroethanol 22.5kg added to the reactor, open The autoclave heats the steam valve so that the pressure inside the kettle is kept at 0.45 ~ 0.50MPa for 1.0 ~ 3.0h. In the course of the reaction, the pressure is measured after the sampling test, otherwise the reaction continues until the qualified.Add 2.5 kg of activated charcoal to the decolorizer for 30 min.The bleach solution is filtered to the storage tank by hot pressing.From the storage tank to filter the good material to the crystallization tank on the crystallization of the cylinder, the water temperature is not higher than 30 , with concentrated hydrochloric acid to adjust the pH value of 3 to 4, crystallization 24 ~ 48h after centrifugation.
YieldReaction ConditionsOperation in experiment
Specifically preferred are compounds selected the group of: Flavone, Baicalein, Diosmin, Kaempferide Tangeretine, 3-OH-Flavone Fisetin, Myricetin, Flavanone, ...
  • 9
  • (<i>S</i>)-5-acetoxy-2-<3-acetoxy-4-methoxy-phenyl>-7-<<i>O</i>2,<i>O</i>3,<i>O</i>4-triacetyl-<i>O</i>6-(tri-<i>O</i>-acetyl-α-L-rhamnopyranosyl)-β-D-glucopyranosyloxy>-chroman-4-one [ No CAS ]
  • [ 520-27-4 ]
  • 10
  • 5-hydroxyheptaacetyldiosmin [ No CAS ]
  • [ 520-27-4 ]
  • 11
  • [ 108-24-7 ]
  • [ 520-27-4 ]
  • [ 6195-54-6 ]
YieldReaction ConditionsOperation in experiment
62% With sodium fluoride; at 130℃; for 0.583333h;Microwave irradiation; Diosmin (2, 0.05 g, 0.08 mmol) and NaF (0.42 g, 10 mmol) were mixed in acetic anhydride (4 mL) and the mixture was kept under MW irradiation (400 W) at 130 C, for 35 min. After cooling, the solution obtained was poured into ice and then extracted with CH2Cl2. The organic layer was extracted with NaHCO3 followed by crystallization from MeOH/H2O provided 5,3-O-acetyl-2-(3-O-acetyl-4-methoxyphenyl)-7-[2,3,4-tri-O-acetyl-alpha-L-rhamnopyranosyl-(16)-2,3,4-tri-O-acetyl-beta-D-glucopyranosyloxy] oxychromen-4-one (6) as a yellow solid (0.048 g, 0.051 mmol, 62 % yield); mp 135-138 C.
  • 12
  • [ 14210-25-4 ]
  • [ 520-27-4 ]
  • [ 771480-96-7 ]
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Technical Information

? Appel Reaction ? Baeyer-Villiger Oxidation ? Barbier Coupling Reaction ? Baylis-Hillman Reaction ? Benzylic Oxidation ? Birch Reduction ? Blanc Chloromethylation ? Bucherer-Bergs Reaction ? Buchwald-Hartwig C-N Bond and C-O Bond Formation Reactions ? Chugaev Reaction ? Clemmensen Reduction ? Corey-Bakshi-Shibata (CBS) Reduction ? Corey-Chaykovsky Reaction ? Corey-Kim Oxidation ? Dess-Martin Oxidation ? Fischer Indole Synthesis ? Friedel-Crafts Reaction ? Grignard Reaction ? Henry Nitroaldol Reaction ? Horner-Wadsworth-Emmons Reaction ? Hydride Reductions ? Hydrogenolysis of Benzyl Ether ? Jones Oxidation ? Lawesson's Reagent ? Leuckart-Wallach Reaction ? Martin's Sulfurane Dehydrating Reagent ? McMurry Coupling ? Meerwein-Ponndorf-Verley Reduction ? Mitsunobu Reaction ? Moffatt Oxidation ? Nomenclature of Ethers ? Oxidation of Alcohols by DMSO ? Passerini Reaction ? Paternò-Büchi Reaction ? Petasis Reaction ? Peterson Olefination ? Pictet-Spengler Tetrahydroisoquinoline Synthesis ? Preparation of Alcohols ? Preparation of Aldehydes and Ketones ? Preparation of Alkylbenzene ? Preparation of Amines ? Preparation of Ethers ? Prins Reaction ? Reactions of Alcohols ? Reactions of Aldehydes and Ketones ? Reactions of Amines ? Reactions of Benzene and Substituted Benzenes ? Reactions of Ethers ? Reactions with Organometallic Reagents ? Reformatsky Reaction ? Ritter Reaction ? Robinson Annulation ? Schlosser Modification of the Wittig Reaction ? Schmidt Reaction ? Sharpless Olefin Synthesis ? Specialized Acylation Reagents-Ketenes ? Stobbe Condensation ? Swern Oxidation ? Tebbe Olefination ? Ugi Reaction ? Vilsmeier-Haack Reaction ? Wittig Reaction ? Wolff-Kishner Reduction
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2-(3,4-Dihydroxyphenyl)-2-((2-(3,4-dihydroxyphenyl)-5,7-dihydroxychroman-3-yl)oxy)chroman-3,4,5,7-tetraol

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Chemical Structure| 67604-48-2

[ 67604-48-2 ]

5,7-Dihydroxy-2-(4-hydroxyphenyl)chroman-4-one

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Tetrahydropyrans

Chemical Structure| 578-74-5

[ 578-74-5 ]

5-Hydroxy-2-(4-hydroxyphenyl)-7-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-4H-chromen-4-one

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Chemical Structure| 25694-72-8

[ 25694-72-8 ]

7-(((2S,3R,4S,5S,6R)-4,5-Dihydroxy-6-(hydroxymethyl)-3-(((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)tetrahydro-2H-pyran-2-yl)oxy)-2-(3,4-dihydroxyphenyl)-5-hydroxy-4H-chromen-4-one

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Chemical Structure| 14259-46-2

[ 14259-46-2 ]

(S)-5-Hydroxy-2-(4-hydroxyphenyl)-7-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-((((2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)methyl)tetrahydro-2H-pyran-2-yl)oxy)chroman-4-one

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Chemical Structure| 123063-33-2

[ 123063-33-2 ]

8-(((2S,3R,4S,5S,6R)-4,5-Dihydroxy-6-(hydroxymethyl)-3-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)tetrahydro-2H-pyran-2-yl)oxy)-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one

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Chemical Structure| 64820-99-1

[ 64820-99-1 ]

8-((2S,3R,4S,5S,6R)-4,5-Dihydroxy-6-(hydroxymethyl)-3-(((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)tetrahydro-2H-pyran-2-yl)-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one

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