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[ CAS No. 480-41-1 ] {[proInfo.proName]}

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Chemical Structure| 480-41-1
Chemical Structure| 480-41-1
Structure of 480-41-1 * Storage: {[proInfo.prStorage]}
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Product Details of [ 480-41-1 ]

CAS No. :480-41-1 MDL No. :MFCD00870553
Formula : C15H12O5 Boiling Point : -
Linear Structure Formula :- InChI Key :FTVWIRXFELQLPI-ZDUSSCGKSA-N
M.W :272.25 Pubchem ID :439246
Synonyms :
Naringenin

Calculated chemistry of [ 480-41-1 ]

Physicochemical Properties

Num. heavy atoms : 20
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.13
Num. rotatable bonds : 1
Num. H-bond acceptors : 5.0
Num. H-bond donors : 3.0
Molar Refractivity : 71.57
TPSA : 86.99 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : Yes
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : Yes
Log Kp (skin permeation) : -6.17 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.75
Log Po/w (XLOGP3) : 2.52
Log Po/w (WLOGP) : 2.19
Log Po/w (MLOGP) : 0.71
Log Po/w (SILICOS-IT) : 2.05
Consensus Log Po/w : 1.84

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.49
Solubility : 0.0874 mg/ml ; 0.000321 mol/l
Class : Soluble
Log S (Ali) : -3.99
Solubility : 0.0277 mg/ml ; 0.000102 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.42
Solubility : 0.104 mg/ml ; 0.000382 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 3.01

Safety of [ 480-41-1 ]

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 [ 480-41-1 ]

* 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 [ 480-41-1 ]
  • Downstream synthetic route of [ 480-41-1 ]

[ 480-41-1 ] Synthesis Path-Upstream   1~19

  • 1
  • [ 480-41-1 ]
  • [ 578-74-5 ]
Reference: [1] Tetrahedron, 2004, vol. 60, # 9, p. 2025 - 2034
  • 2
  • [ 10236-47-2 ]
  • [ 480-41-1 ]
YieldReaction ConditionsOperation in experiment
26.9% With hydrogenchloride In water at 100℃; for 1 h; A mixture of 52 g of naringin and 5 w / vpercent of hydrochloric acid was mixed at a solid-to-liquid ratio of 1: 100 g / mL and hydrolyzed at 100 ° C for 1 hour. And then quickly cooled to room temperature, and then put it aside for 12 hours, precipitation of solid, after filtration with purified water to wash the solid to neutral, and then filtered to 25percent moisture content of naringenin wet crude 24. 5 grams; The crude naringenin obtained in the step (1) was added to a 30W / Vpercent acetic acid solution at a solid-to-liquid ratio of 1: 7g / mL, stirred at room temperature for 30 minutes, and then the solid was added to the same concentration Of acetic acid solution for 15 minutes, and then filtered, the solid washed with water to neutral, and then solid-liquid ratio of 1: 10g / mL volume concentration of 95percent ethanol dissolved, and then neutral alumina chromatography column, 100mL volume concentration of 95percent ethanol column chromatography column combined solution after the column, and then added to the solution volume of 10percent activated carbon at room temperature for 30 minutes, after filtration, the filtrate and then add the solution volume 10 The activated carbon was stirred at room temperature for 30 minutes. After filtration, the filtrate was concentrated to 1/3 volume by volume, distilled water was added into the same volume of distilled water, cooled to room temperature and placed in the refrigerator at 5 ° C for 24 hours. And then the white nacre crystals are precipitated and filtered to obtain naringenin wet fine product. The naringenin wet boutique is heated and boiled with 95percent ethanol by solid-liquid ratio of l: 6g / mL, and dissolved in ethanol An equal volume of distilled water was recrystallized once, and the precipitated white needle-like crystals were collected by filtration and then dried to obtain naringenin 14 g. In this case, the content of naringenin was 99.92percent and the yield was 26.9percent.
4.62 g at 90℃; Taking 98percent naringin 10g, macroporous resin D101 type 100g (about 200 ml), is placed in the 500 ml triangle flask, add 6percent sulfuric acid (6 ml _AOE 28692X0AO _ 100 ml) 150 ml, is connected to the 30 cm - 40 cm air condensing tube, water bath 90 °C closed hydrolysis 48h (macroporous resin by the white-light yellow, colorless solution), remove and cool, filtered, macroporous resin to a little water to wash, macroporous resin end to burn in the cup, add 300 ml water liquid, adding sodium bicarbonate, to neutral, filtered, 200 ml water washing, drying, using ethanol as solvent, reflux extraction 3 times (macroporous resin recovery white), each 20min, combined ethanol solution, decompression recovering ethanol, to obtain white of the naringenin 4.62g, determine its purity by HPLC is 94.5percent.
Reference: [1] Patent: CN103467428, 2016, B, . Location in patent: Paragraph 0017-0020
[2] Phytochemistry, 2005, vol. 66, # 14, p. 1698 - 1706
[3] Journal of Agricultural and Food Chemistry, 2013, vol. 61, # 4, p. 931 - 938
[4] Patent: CN103772337, 2017, B, . Location in patent: Paragraph 0030-0033
  • 3
  • [ 10236-47-2 ]
  • [ 492-61-5 ]
  • [ 6014-42-2 ]
  • [ 480-41-1 ]
Reference: [1] Journal of Molecular Catalysis B: Enzymatic, 2014, vol. 105, p. 95 - 103
  • 4
  • [ 10236-47-2 ]
  • [ 19949-48-5 ]
  • [ 480-41-1 ]
Reference: [1] Food Chemistry, 2011, vol. 127, # 2, p. 394 - 403
  • 5
  • [ 60-18-4 ]
  • [ 7400-08-0 ]
  • [ 480-41-1 ]
Reference: [1] Patent: WO2016/71505, 2016, A1, . Location in patent: Page/Page column 39; 40
  • 6
  • [ 60-18-4 ]
  • [ 961-29-5 ]
  • [ 7400-08-0 ]
  • [ 578-86-9 ]
  • [ 480-41-1 ]
Reference: [1] Patent: WO2016/71505, 2016, A1, . Location in patent: Page/Page column 39; 40
  • 7
  • [ 10236-47-2 ]
  • [ 2280-44-6 ]
  • [ 73-34-7 ]
  • [ 529-55-5 ]
  • [ 480-41-1 ]
Reference: [1] Journal of Molecular Catalysis B: Enzymatic, 2010, vol. 65, # 1-4, p. 102 - 109
[2] Food Chemistry, 2018, vol. 269, p. 63 - 69
  • 8
  • [ 1160434-47-8 ]
  • [ 50-99-7 ]
  • [ 480-41-1 ]
Reference: [1] Chemical and Pharmaceutical Bulletin, 2009, vol. 57, # 4, p. 361 - 367
  • 9
  • [ 10236-47-2 ]
  • [ 480-41-1 ]
Reference: [1] Bioscience, biotechnology, and biochemistry, 2003, vol. 67, # 7, p. 1443 - 1450
  • 10
  • [ 529-55-5 ]
  • [ 492-62-6 ]
  • [ 480-41-1 ]
Reference: [1] Journal of Agricultural and Food Chemistry, 2013, vol. 61, # 42, p. 10026 - 10032
  • 11
  • [ 10236-47-2 ]
  • [ 529-55-5 ]
  • [ 480-41-1 ]
Reference: [1] Phytochemistry, 2010, vol. 71, # 2-3, p. 201 - 205
  • 12
  • [ 520-29-6 ]
  • [ 480-41-1 ]
Reference: [1] Chemical and Pharmaceutical Bulletin, 2003, vol. 51, # 2, p. 203 - 206
  • 13
  • [ 529-41-9 ]
  • [ 480-41-1 ]
Reference: [1] Archiv der Pharmazie (Weinheim, Germany), 1959, vol. 292, p. 398,408
  • 14
  • [ 529-55-5 ]
  • [ 480-41-1 ]
Reference: [1] Journal of Agricultural and Food Chemistry, 2013, vol. 61, # 4, p. 931 - 938
  • 15
  • [ 112294-87-8 ]
  • [ 480-41-1 ]
Reference: [1] Phytochemistry (Elsevier), 1986, vol. 25, # 6, p. 1431 - 1436
  • 16
  • [ 10236-47-2 ]
  • [ 492-61-5 ]
  • [ 6014-42-2 ]
  • [ 529-55-5 ]
  • [ 480-41-1 ]
Reference: [1] Journal of Molecular Catalysis B: Enzymatic, 2010, vol. 65, # 1-4, p. 91 - 101
  • 17
  • [ 25515-46-2 ]
  • [ 480-41-1 ]
Reference: [1] Planta Medica, 2011, vol. 77, # 7, p. 765 - 770
  • 18
  • [ 480-41-1 ]
  • [ 60-82-2 ]
Reference: [1] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1988, vol. 27, # 1-12, p. 899 - 901
[2] Synthetic Communications, 1989, vol. 19, # 1, 2, p. 119 - 124
[3] Angewandte Chemie - International Edition, 2014, vol. 53, # 5, p. 1439 - 1442[4] Angew. Chem., 2014, vol. 126, # 05, p. 1463 - 1466,4
  • 19
  • [ 60-18-4 ]
  • [ 961-29-5 ]
  • [ 7400-08-0 ]
  • [ 578-86-9 ]
  • [ 480-41-1 ]
Reference: [1] Patent: WO2016/71505, 2016, A1, . Location in patent: Page/Page column 39; 40
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