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[ CAS No. 22395-22-8 ]

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Chemical Structure| 22395-22-8
Chemical Structure| 22395-22-8
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CAS No. :22395-22-8 MDL No. :MFCD00017462
Formula : C16H12O3 Boiling Point : 421.2±45.0°C at 760 mmHg
Linear Structure Formula :- InChI Key :N/A
M.W :252.26 g/mol Pubchem ID :466268
Synonyms :

Safety of [ 22395-22-8 ]

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

Application In Synthesis of [ 22395-22-8 ]

  • Upstream synthesis route of [ 22395-22-8 ]
  • Downstream synthetic route of [ 22395-22-8 ]

[ 22395-22-8 ] Synthesis Path-Upstream   1~57

  • 1
  • [ 52752-67-7 ]
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YieldReaction ConditionsOperation in experiment
92% With malic acid In neat (no solvent) at 140℃; for 0.0833333 h; Microwave irradiation; Green chemistry General procedure: The mixture of 1-(2-hydroxyphenyl)-3-aryl-1,3-propanedione 1a (0.5 g) and malic acid (1.0 eq.) was heatedeither in an oil bath, preheated at 140 °C for 10 min or in amicrowave reactor for 5 min. After the completion of reaction(TLC check), the reaction mixture was allowed to cool;at room temperature water (10 mL) and ethyl acetate (10mL) were added. Reaction mixture was neutralized by additionof solid NaHCO3. Organic layer was separated and theaqueous layer was extracted in ethyl acetate (2 10 mL).Combined organic extract was dried over anhydrous sodiumsulfate and concentrated in vacuo. The crude product waspurified by column chromatography on silica gel using hexane-ethylacetate solvent system to give the correspondingflavones in high yield.
91% With ammonium acetate In neat (no solvent) at 114℃; for 0.0833333 h; Microwave irradiation General procedure: The mixture of 1-(2-hydroxyphenyl)-3-aryl-1,3-propanedione 1a (0.5 g, 2.08 mmol) and ammonium acetate (0.16 g, 2.08 mmol) was heated either in an oil bath, preheated at 114°C for 10 min or in a microwave reactor for 5min. After the pH of the reaction mixture was brought back to 7.0 by the careful addition of NaHCO3 solution. The aqueous layer was extracted with ethyl acetate, dried(Na2SO4), and concentrated in vacuo. The crude product was purified by column chromatography on silica gel using hexane-ethyl acetate solvent system to give the corresponding flavones in high yield.
88% at 180℃; General procedure: The mixture of 1-(2-hydroxyphenyl)-3-aryl-1,3-propanedione 4a-q (0.5g, 2.08 mmol) and L-ascorbic acid(3.7g, 2.08 mmol) was heated on a preheated oil bath or undermicrowave irradiation at 180 °C for 2-3 min. After completionof reaction (TLC check), the reaction mixture wascooled to room temperature and the flask was sonicated byadding excess water. The crude product was filtered oversuction-pump and washed with excess of water to removeL-ascorbic acid. The solid obtained was dried and crystallizedby using ethanol to give the corresponding flavones inhigh yield. The purity of products was confirmed by satisfactoryspectroscopic data.
70% With sodium acetate In acetic acid EXAMPLE 2
Synthesis of 7-Methoxy-2-phenyl-chromen-4-one (Compound 2)
240 mg (0.89 mmol) of 1-(2-hydroxy-4-methoxy-phenyl)-3-phenyl-propan-1,3-dione was dissolved in acetic acid, and 0.73 g (8.9 mmol) of sodium acetate was added thereto.
The mixture was refluxed overnight.
Acetic acid was removed by distillation under reduced pressure, and then the residue was purified by silica gel column chromatography (eluent: n-hexane/ethylacetate=5/1, v/v) to give the title compound in a yield of 70percent.
1H NMR (500 MHz, CDCl3): δ 8.20 (m, 1H), 7.91 (m, 2H), 7.55 (m, 3H), 6.97 (m, 3H), 3.90 (s, 3H); MS (FAB): 253 (M+H+).
57% at 100℃; for 1 h; General procedure: Compounds 4a–j (1.8 g) glycerol triacetate (10 mL) and concentrated sulfuric acid (0.4 mL) wereplaced in a round bottomed flask equipped with a reflux condenser, stirred about 1 h at 100 C andthen the mixture was poured into a beaker containing 50 g of crushed ice, where solids were formedafter stirring and then filtered from the solution, Next the solids were washed with water until the acidwas removed. Finally, the solids were purified and separated by column chromatography eluting witha mixed petroleum ether and ethyl acetate solvent until the final products 5a–j were obtained.

Reference: [1] Letters in Organic Chemistry, 2014, vol. 11, # 8, p. 601 - 605
[2] Heterocyclic Communications, 2007, vol. 13, # 1, p. 77 - 81
[3] Letters in Organic Chemistry, 2015, vol. 12, # 8, p. 574 - 583
[4] Letters in Organic Chemistry, 2016, vol. 13, # 10, p. 734 - 741
[5] Bulletin of the Chemical Society of Japan, 1987, vol. 60, # 5, p. 1919 - 1920
[6] Patent: US6500846, 2002, B1,
[7] Molecules, 2018, vol. 23, # 9,
[8] Journal of the University of Bombay, Science: Physical Sciences, Mathematics, Biological Sciences and Medicine, 1942, vol. 11/3 A, p. 140
[9] Journal of Organic Chemistry, 1991, vol. 56, # 26, p. 7292 - 7297
[10] Synthesis, 1992, # 9, p. 839 - 841
[11] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2012, vol. 51, # 5, p. 770 - 773
[12] European Journal of Medicinal Chemistry, 2012, vol. 50, p. 428 - 432
[13] Synthetic Communications, 2013, vol. 43, # 11, p. 1549 - 1556
[14] Patent: CN106083793, 2016, A, . Location in patent: Paragraph 0030; 0031
  • 2
  • [ 552-41-0 ]
  • [ 100-52-7 ]
  • [ 22395-22-8 ]
YieldReaction ConditionsOperation in experiment
88% With pyrrolidine; iodine In dimethyl sulfoxide at 150℃; for 10 h; General procedure: 2'-Hydroxyacetophenone (1 mmol) and substituted aromatic aldehyde (1 mmol) were mixed together along with pyrrolidine (0.5 mmol) and iodine (0.05 mmol) in DMSO solvent (10 mL). The resulting mixture was then heated at 150 °C for the given time. After completion of reaction (monitored by TLC) the reaction mass was allowed to cool and diluted with ethyl acetate (20 mL). Resulting solution was then washed with water and saturated sodium thiosulfate solution followed by drying over anhydrous sodium sulfate and concentrating under reduced pressure to furnish the crude product. The residue obtained was purified by column chromatography using petroleum ether-ethyl acetate as an eluent to afford flavones (3a–r).
Reference: [1] Tetrahedron Letters, 2014, vol. 55, # 22, p. 3340 - 3343
[2] Angewandte Chemie - International Edition, 2015, vol. 54, # 45, p. 13302 - 13306[3] Angew. Chem., 2015, vol. 127, # 45, p. 13500 - 13504,5
[4] Organic and Biomolecular Chemistry, 2011, vol. 9, # 20, p. 6930 - 6933
  • 3
  • [ 98153-26-5 ]
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YieldReaction ConditionsOperation in experiment
74% With dmap In N,N-dimethyl-formamide at 0 - 30℃; for 4 h; Inert atmosphere General procedure: To a solution of o-alkynoylphenol 3 or 6 in DMF (4 mL/mmol) was added DMAP (10 mol percent) at 0 °C under argon. After being stirred at 30 °C, the reaction mixture was diluted with water. The aqueous layer was extracted twice with ethyl acetate. The organic layer was washed with 1 M HCl, saturated aqueous NaHCO3, brine, dried over MgSO4, and filtered. The filtrate was concentrated in vacuo, and then the resulting residue was purified by column chromatography on silica gel to afford flavone 1 or 7. Spectral data of flavones 1a-1n and 7a-7c have been reported previously10.
Reference: [1] Tetrahedron, 2011, vol. 67, # 51, p. 9993 - 9997
[2] Organic Letters, 2011, vol. 13, # 17, p. 4526 - 4529
[3] Advanced Synthesis and Catalysis, 2018, vol. 360, # 1, p. 153 - 160
  • 4
  • [ 21785-09-1 ]
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Reference: [1] Bulletin of the Chemical Society of Japan, 1985, vol. 58, # 5, p. 1599 - 1600
[2] Journal of Organic Chemistry, 2015, vol. 80, # 12, p. 6400 - 6410
[3] Advanced Synthesis and Catalysis, 2006, vol. 348, # 1-2, p. 63 - 67
[4] Organic Letters, 2016, vol. 18, # 17, p. 4190 - 4193
[5] Tetrahedron, 2010, vol. 66, # 32, p. 6047 - 6053
[6] Synthetic Communications, 1982, vol. 12, # 12, p. 927 - 930
[7] Journal of Chemical Research, 2008, # 4, p. 225 - 226
[8] Synthesis, 1983, # 4, p. 310 - 311
[9] Proceedings - Indian Academy of Sciences, Section A, 1952, # 36, p. 134,137
[10] Proceedings - Indian Academy of Sciences, Section A, 1949, # 30, p. 151,157
[11] Proceedings - Indian Academy of Sciences, Section A, 1949, # 30, p. 151,157
  • 5
  • [ 4136-21-4 ]
  • [ 100-52-7 ]
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YieldReaction ConditionsOperation in experiment
90% at 70℃; for 6 h; In 10 ml in the reaction kettle, successively added 0.3183g (3mmol) benzaldehyde, 0.3323g (2mmol) 4-methoxy-2-hydroxy acetophenone and 0.2630g (0.6mmol) of the ionic liquid catalyst [Bmim]2[MoO4] (structural formula refer to embodiment 1), and 0.8170g (8mmol) tetrahydrofururyl alcohol solvent, stirring after mixing, heating to reaction temperature 70 °C, in 0.4 MPa stir to react under oxygen atmosphere 6h, cooled to the room temperature after the reaction, the solvent is removed by reduced pressure distillation after of tetrahydrofurfuryl alcohol, adding ethyl acetate and water extraction, the split-phase, passes through the column again chromatography and recrystallization of relative separation to obtain the target product 7-methoxy-flavone, the yield is 90percent, the nuclear magnetic resonance hydrogen spectrum, carbon spectrum and high-resolution mass spectrometry to determine its structural formula is:
Reference: [1] Patent: CN105294627, 2016, A, . Location in patent: Paragraph 0100; 0101; 0102
  • 6
  • [ 52923-29-2 ]
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[4] Organic and Biomolecular Chemistry, 2011, vol. 9, # 20, p. 6930 - 6933
[5] Drug Development Research, 2015, vol. 76, # 8, p. 450 - 462
[6] Tetrahedron Letters, 1990, vol. 31, # 50, p. 7355 - 7356
[7] Synlett, 2008, # 20, p. 3167 - 3171
[8] Bioorganic and Medicinal Chemistry, 2010, vol. 18, # 3, p. 1273 - 1279
  • 7
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  • 8
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[2] Synthetic Communications, 1993, vol. 23, # 7, p. 1021 - 1023
[3] Bulletin of the Chemical Society of Japan, 1986, vol. 59, # 7, p. 2351 - 2352
[4] Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 5, p. 1165 - 1167
  • 9
  • [ 201230-82-2 ]
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  • [ 22395-22-8 ]
  • [ 31356-11-3 ]
Reference: [1] Tetrahedron, 1991, vol. 47, # 32, p. 6449 - 6456
  • 10
  • [ 1415384-96-1 ]
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  • [ 127839-71-8 ]
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[2] Chemical Communications, 2012, vol. 48, # 96, p. 11796 - 11798
  • 11
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  • [ 42327-52-6 ]
  • [ 22395-22-8 ]
Reference: [1] Organic and Biomolecular Chemistry, 2015, vol. 14, # 2, p. 777 - 784
[2] Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 11, p. 2613 - 2616
  • 12
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  • [ 22395-22-8 ]
Reference: [1] Angewandte Chemie, International Edition, 2012, vol. 51, # 45, p. 11333 - 11336,4
  • 13
  • [ 108-86-1 ]
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Reference: [1] Chemistry - A European Journal, 2012, vol. 18, # 40, p. 12595 - 12598
  • 14
  • [ 1403475-70-6 ]
  • [ 22395-22-8 ]
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  • 15
  • [ 959-23-9 ]
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Reference: [1] Journal of Organometallic Chemistry, 2013, vol. 734, p. 78 - 85
  • 16
  • [ 21785-09-1 ]
  • [ 22395-22-8 ]
  • [ 153446-72-1 ]
Reference: [1] Organic Letters, 2016, vol. 18, # 17, p. 4190 - 4193
  • 17
  • [ 673-22-3 ]
  • [ 70-11-1 ]
  • [ 22395-22-8 ]
Reference: [1] European Journal of Organic Chemistry, 2018, vol. 2018, # 4, p. 537 - 544
  • 18
  • [ 124260-01-1 ]
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[2] Synthesis, 1992, # 9, p. 839 - 841
[3] Journal of Organic Chemistry, 1991, vol. 56, # 26, p. 7292 - 7297
[4] Medicinal Chemistry, 2018, vol. 14, # 2, p. 181 - 199
[5] Molecules, 2018, vol. 23, # 9,
  • 19
  • [ 21785-09-1 ]
  • [ 22395-22-8 ]
  • [ 1621-56-3 ]
Reference: [1] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1993, vol. 32, # 9, p. 911 - 915
[2] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1993, vol. 32, # 9, p. 911 - 915
[3] Tetrahedron Letters, 1990, vol. 31, # 50, p. 7355 - 7356
  • 20
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  • [ 22395-22-8 ]
Reference: [1] Organic and Biomolecular Chemistry, 2012, vol. 10, # 36, p. 7305 - 7312
[2] Chemical Communications, 2012, vol. 48, # 24, p. 2985 - 2987
  • 21
  • [ 21785-09-1 ]
  • [ 22395-22-8 ]
Reference: [1] Advanced Synthesis and Catalysis, 2006, vol. 348, # 1-2, p. 63 - 67
  • 22
  • [ 673-22-3 ]
  • [ 22395-22-8 ]
Reference: [1] Tetrahedron, 1988, vol. 44, # 11, p. 3187 - 3194
[2] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1990, # 2, p. 423 - 424
[3] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1990, # 2, p. 423 - 424
[4] Organic Letters, 2011, vol. 13, # 17, p. 4526 - 4529
[5] Tetrahedron, 2011, vol. 67, # 51, p. 9993 - 9997
[6] Advanced Synthesis and Catalysis, 2018, vol. 360, # 1, p. 153 - 160
  • 23
  • [ 552-41-0 ]
  • [ 22395-22-8 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 5, p. 1165 - 1167
[2] Journal of Organic Chemistry, 1991, vol. 56, # 26, p. 7292 - 7297
[3] Chemical Communications, 2012, vol. 48, # 24, p. 2985 - 2987
[4] European Journal of Medicinal Chemistry, 2012, vol. 50, p. 428 - 432
[5] RSC Advances, 2015, vol. 5, # 124, p. 102191 - 102203
[6] Drug Development Research, 2015, vol. 76, # 8, p. 450 - 462
[7] Patent: CN106083793, 2016, A,
[8] Medicinal Chemistry, 2018, vol. 14, # 2, p. 181 - 199
[9] Molecules, 2018, vol. 23, # 9,
  • 24
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  • [ 616-38-6 ]
  • [ 22395-22-8 ]
Reference: [1] Molecules, 2011, vol. 16, # 2, p. 1418 - 1425
  • 25
  • [ 673-22-3 ]
  • [ 698-88-4 ]
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Reference: [1] Chemical Communications, 2015, vol. 51, # 99, p. 17576 - 17579
  • 26
  • [ 1322775-64-3 ]
  • [ 22395-22-8 ]
Reference: [1] Organic Letters, 2011, vol. 13, # 17, p. 4526 - 4529
[2] Tetrahedron, 2011, vol. 67, # 51, p. 9993 - 9997
[3] Advanced Synthesis and Catalysis, 2018, vol. 360, # 1, p. 153 - 160
  • 27
  • [ 536-74-3 ]
  • [ 22395-22-8 ]
Reference: [1] Organic Letters, 2011, vol. 13, # 17, p. 4526 - 4529
[2] Tetrahedron, 2011, vol. 67, # 51, p. 9993 - 9997
[3] Advanced Synthesis and Catalysis, 2018, vol. 360, # 1, p. 153 - 160
  • 28
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Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1990, # 2, p. 423 - 424
  • 29
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Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1990, # 2, p. 423 - 424
  • 30
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  • [ 74-88-4 ]
  • [ 22395-22-8 ]
Reference: [1] Tetrahedron Letters, 2005, vol. 46, # 32, p. 5399 - 5402
[2] Proceedings - Indian Academy of Sciences, Section A, 1949, # 29, p. 314,318
  • 31
  • [ 98-88-4 ]
  • [ 22395-22-8 ]
Reference: [1] Patent: CN106083793, 2016, A,
[2] Medicinal Chemistry, 2018, vol. 14, # 2, p. 181 - 199
[3] Molecules, 2018, vol. 23, # 9,
  • 32
  • [ 89-84-9 ]
  • [ 22395-22-8 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 5, p. 1165 - 1167
[2] RSC Advances, 2015, vol. 5, # 124, p. 102191 - 102203
[3] Drug Development Research, 2015, vol. 76, # 8, p. 450 - 462
  • 33
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  • 34
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Reference: [1] Synthesis, 1987, # 2, p. 199 - 201
  • 36
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  • 37
  • [ 17336-11-7 ]
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Reference: [1] European Journal of Organic Chemistry, 2012, # 24, p. 4533 - 4540,8
  • 38
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Reference: [1] European Journal of Organic Chemistry, 2012, # 24, p. 4533 - 4540,8
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[2] Monatshefte fuer Chemie, 1991, vol. 122, # 1.2, p. 83 - 87
  • 40
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  • 41
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Reference: [1] Journal of Heterocyclic Chemistry, 1993, vol. 30, # 1, p. 145 - 151
  • 42
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Reference: [1] Monatshefte fuer Chemie, 1991, vol. 122, # 1.2, p. 83 - 87
  • 43
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Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1990, # 2, p. 423 - 424
[2] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1990, # 2, p. 423 - 424
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Reference: [1] European Journal of Medicinal Chemistry, 2012, vol. 50, p. 428 - 432
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Reference: [1] Journal of the Chemical Society, 1954, p. 4573,4580
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[ 5751-52-0 ]

7-Methoxy-4H-chromen-4-one

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Chemical Structure| 10176-66-6

[ 10176-66-6 ]

5,7-Dihydroxy-6,8-dimethoxy-2-(4-methoxyphenyl)-4H-chromen-4-one

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Chemical Structure| 1157-39-7

[ 1157-39-7 ]

4',7-Dimethoxyisoflavone

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Related Parent Nucleus of
[ 22395-22-8 ]

Other Aromatic Heterocycles

Chemical Structure| 26964-24-9

[ 26964-24-9 ]

6-Methoxy-2-phenyl-4H-chromen-4-one

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Chemical Structure| 525-82-6

[ 525-82-6 ]

2-Phenyl-4H-chromen-4-one

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Chemical Structure| 144707-18-6

[ 144707-18-6 ]

2',3',4'-Trihydroxyflavone

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Chemical Structure| 480-40-0

[ 480-40-0 ]

5,7-Dihydroxy-2-phenyl-4H-chromen-4-one

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[ 6320-42-9 ]

7-Hydroxy-2-methyl-4H-chromen-4-one

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