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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
Structure of 520-27-4 * Storage: {[proInfo.prStorage]}
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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

Calculated chemistry of [ 520-27-4 ]

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 Ų

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.

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

[ 520-27-4 ] Synthesis Path-Upstream   1~3

  • 1
  • [ 520-26-3 ]
  • [ 520-27-4 ]
YieldReaction ConditionsOperation in experiment
85.7% 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 30percent 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 99.27percent), 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 99.44percent, the yield is 85.7percent, to the solvent recovery rate 80.1percent, iodine recovery rate 89.6percent, residual solvent, -related impurities are standard.
13.1 g
Stage #1: With potassium borohydride; sulfuric acid In dimethyl sulfoxide for 0.5 h;
Stage #2: With iodine In pyridine; pentan-1-ol at 55℃; for 96 h;
Take an amount of 95percent 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 0.1percent 0.5percent phosphoric acid vitamin C400ml further elution remove residual iodine, pyridine and other impurities, washed with water 300ml, 2000ml eluted with 60percent 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 1.0percent 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 ~ 15percent to obtain crude product 108kg. The crude product was put into the reactor, added 864kg, 648kg and 432kg of 85percent 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.
Reference: [1] Archiv der Pharmazie, 1983, vol. 316, # 3, p. 219 - 222
[2] Patent: CN105732744, 2016, A, . Location in patent: Paragraph 0040; 0041
[3] Proceedings - Indian Academy of Sciences, Section A, 1949, # 30, p. 151,157
[4] Patent: WO2010/92592, 2010, A2, . Location in patent: Page/Page column 9; 10
[5] Patent: CN105481918, 2016, A, . Location in patent: Paragraph 0025
[6] Patent: CN103435666, 2016, B, . Location in patent: Paragraph 0016
  • 2
  • [ 64726-90-5 ]
  • [ 520-27-4 ]
Reference: [1] Patent: WO2016/124585, 2016, A1,
  • 3
  • [ 69081-76-1 ]
  • [ 520-27-4 ]
Reference: [1] Chemische Berichte, 1943, vol. 76, p. 452,457
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