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[ CAS No. 578-74-5 ] {[proInfo.proName]}

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Chemical Structure| 578-74-5
Chemical Structure| 578-74-5
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Quality Control of [ 578-74-5 ]

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Product Details of [ 578-74-5 ]

CAS No. :578-74-5 MDL No. :MFCD00016787
Formula : C21H20O10 Boiling Point : No data available
Linear Structure Formula :C15H9O5(C6H11O5) InChI Key :KMOUJOKENFFTPU-QNDFHXLGSA-N
M.W : 432.38 Pubchem ID :5280704
Synonyms :
Chemical Name :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

Safety of [ 578-74-5 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P305+P351+P338 UN#:
Hazard Statements:H302-H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 578-74-5 ]

* 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 [ 578-74-5 ]

[ 578-74-5 ] Synthesis Path-Upstream   1~14

  • 1
  • [ 119249-30-8 ]
  • [ 578-74-5 ]
YieldReaction ConditionsOperation in experiment
72% With water; ammonium hydroxide In methanol at 20℃; for 12 h; Compound 1 (150 mg, 0.25 mmol) was added to a solution of 30percent aq NH3*H2O (5 mL) in CH3OH (20 mL) with stirring. After stirring for 12 h at room temperature, the solvent was removed under reduced pressure. The residual was chromatographed on silica gel using ethyl acetate/MeOH (3:1) as eluent to afford the yellow solid 78 mg, yield: 72percent. Mp 234-236 °C. (lit. 13, 238-239 °C); IR (KBr, cm-1) 3440, 2918, 1615, 1563, 1452, 1346, 1273, 1245, 1146, 1103, 1072, 1024, 895; 1H NMR (400 MHz, DMSO-d6) δ 12.97 (s, 1H, OH-5), 10.48 (s, 1H, OH-4'), 7.96 (d, J = 8.8 Hz, 2H, H-2', H-6'), 6.94 (d, J = 8.8 Hz, 2H, H-3', H-5'), 6.87 (s, 1H, H-3), 6.83 (d, J = 1.6 Hz, 1H, H-8), 6.45 (d, J = 1.6 Hz, 1H, H-6), 5.42 (d, J = 8.0 Hz, 1H, H-1), 5.15 (s, 1H, OH-2), 5.08 (s, 1H, OH-3), 5.06 (s, 1H, OH-4), 4.63 (s, 1H, OH-6), 3.72-3.70 (m, 1H, H-2), 3.49-3.18 (m, 5H, H-3,4,5, 6); 13C NMR (100 MHz, DMSO-d6) δ 60.6, 69.6, 73.1, 76.5, 77.2, 94.8, 99.6, 99.9, 103.1, 105.4, 116.0, 121.1, 128.6, 156.9, 161.1, 161.4, 163.0, 164.3, 180.1; HRMS [M+Na]+ calcd for C21H20O10Na 455.3665, found 455.3649.
Reference: [1] Tetrahedron, 2004, vol. 60, # 9, p. 2025 - 2034
[2] Carbohydrate Research, 2012, vol. 357, p. 41 - 46
  • 2
  • [ 1145669-48-2 ]
  • [ 578-74-5 ]
YieldReaction ConditionsOperation in experiment
77% With sodium methylate In methanol; dichloromethane at 20℃; Compound 9a (104 mg, 0.1 mmol) was dissolved in CH2Cl2 (2 mL) and anhydrous methanol (3 mL) was added. Sodium methoxide (100 mg, 1.85 mmol) was then added and the reaction was stirred at room temperature and monitored by TLC. Upon completion, the reaction was neutralized by adding freshly prepared 1 M HCl/MeOH solution to a pH value of 7.4. The solution was then concentrated under reduced pressure to give a yellow oil (crude product), which was further purified by preparative TLC plate to afford glycoside 9b as a white solid, 33 mg, 77percent. 1H NMR (400 MHz, DMSO-d6) δ 7.95 (d, J = 8.8 Hz, 2H), 6.97 (d, J = 8.8 Hz, 2H), 6.86 (s, 1H), 6.84 (d, J = 1.4 Hz, 1H), 6.44 (d, J = 1.8 Hz, 1H), 5.07 (d, J = 7.5 Hz, 1H), 3.71 (d, J = 10.7 Hz, 1H), 3.47 – 3.21 (m, 5H); 13C NMR (100 MHz, DMSO-d6) δ 182.45 (C-4), 164.81 (C-7), 163.41 (C-2), 162.29 (C-5), 161.58 (C-9), 157.41 (C-4'), 129.05 (C-2',6'), 121.15 (C-1'), 116.58 (C-3',5'), 105.79 (C-10), 103.42 (C-3), 100.34 (Glc-C-1), 99.98 (C-6), 95.29 (C-8), 77.63 (Glc-C-3), 76.91 (Glc-C-5), 73.58 (Glc-C-2), 69.99 (Glc-C-4), 61.02 (Glc-C-6).
Reference: [1] Tetrahedron Letters, 2018, vol. 59, # 50, p. 4442 - 4447
  • 3
  • [ 17306-46-6 ]
  • [ 520-36-5 ]
  • [ 578-74-5 ]
YieldReaction ConditionsOperation in experiment
3.4 g
Stage #1: With aluminium(III) chloride hexahydrate In methanol at 70℃; for 15 h; Sealed tube
Stage #2: With phosphoric acid In methanol for 0.5 h; Sonication
5.0 g of 6H2O-aluminum trichloride, 100 ml of methanol,98percent wild luteolin 10g,70 sealed hydrolysis 15h, Adding phosphoric acid 6ml,Mixing,Ultrasound 30min,Adding 0.1percent phosphoric acid in 1000ml of the solution with stirring slowly, placing the mixture for 30 minutes, placing overnight, filtering and washing the filter cake to obtain a mixture of wild erosin, apigenin-7-O-glucoside and apigenin; The column was eluted with chloroform-methanol (12: 1), then apigenin was first eluted, and the ratio of chloroform to methanol was adjusted to (6: 1) to give apigenin-7-O- Glucoside 3.4g, determined by HPLC content of 98.3percent, and finally out of a small amount of wild lacquer glycosides
Reference: [1] Patent: CN105481916, 2016, A, . Location in patent: Paragraph 0018
  • 4
  • [ 133-89-1 ]
  • [ 2196-14-7 ]
  • [ 578-74-5 ]
Reference: [1] Nature Communications, 2017, vol. 8, # 1,
  • 5
  • [ 31087-58-8 ]
  • [ 578-74-5 ]
Reference: [1] Tetrahedron, 2004, vol. 60, # 9, p. 2025 - 2034
  • 6
  • [ 480-41-1 ]
  • [ 578-74-5 ]
Reference: [1] Tetrahedron, 2004, vol. 60, # 9, p. 2025 - 2034
  • 7
  • [ 572-09-8 ]
  • [ 578-74-5 ]
Reference: [1] Tetrahedron, 2004, vol. 60, # 9, p. 2025 - 2034
  • 8
  • [ 23598-19-8 ]
  • [ 578-74-5 ]
Reference: [1] Carbohydrate Research, 2012, vol. 357, p. 41 - 46
  • 9
  • [ 52309-82-7 ]
  • [ 578-74-5 ]
Reference: [1] Carbohydrate Research, 2012, vol. 357, p. 41 - 46
  • 10
  • [ 10236-47-2 ]
  • [ 578-74-5 ]
Reference: [1] Carbohydrate Research, 2012, vol. 357, p. 41 - 46
  • 11
  • [ 26544-34-3 ]
  • [ 2280-44-6 ]
  • [ 30738-01-3 ]
  • [ 139759-42-5 ]
  • [ 578-74-5 ]
Reference: [1] Liebigs Annalen der Chemie, 1992, # 6, p. 575 - 580
  • 12
  • [ 26544-34-3 ]
  • [ 2280-44-6 ]
  • [ 520-36-5 ]
  • [ 139759-42-5 ]
  • [ 578-74-5 ]
Reference: [1] Liebigs Annalen der Chemie, 1992, # 6, p. 575 - 580
  • 13
  • [ 123656-62-2 ]
  • [ 107-93-7 ]
  • [ 578-74-5 ]
Reference: [1] Chemistry of Natural Compounds, 1989, vol. 25, p. 303 - 308[2] Khimiya Prirodnykh Soedinenii, 1989, # 3, p. 352 - 359
  • 14
  • [ 520-36-5 ]
  • [ 572-09-8 ]
  • [ 578-74-5 ]
Reference: [1] Yakugaku Zasshi, 1940, vol. 60, p. 502,505; engl. Ref. S. 190[2] Chem.Abstr., 1941, p. 4022
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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
Historical Records

Related Functional Groups of
[ 578-74-5 ]

Aryls

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[ 520-27-4 ]

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

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(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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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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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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Chemical Structure| 18916-17-1

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1-(4-(((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)-2,6-dihydroxyphenyl)-3-(4-hydroxyphenyl)propan-1-one

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Ethers

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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

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Chemical Structure| 14259-46-2

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(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| 25694-72-8

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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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Alcohols

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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

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(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| 18916-17-1

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Chemical Structure| 18916-17-1

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Chemical Structure| 520-27-4

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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

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2-(3,4-Bis(2-hydroxyethoxy)phenyl)-5-hydroxy-7-(2-hydroxyethoxy)-3-(((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

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Chemical Structure| 520-33-2

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Tetrahydropyrans

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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

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Chemical Structure| 14259-46-2

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(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| 25694-72-8

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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| 64820-99-1

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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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Chemical Structure| 18916-17-1

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1-(4-(((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)-2,6-dihydroxyphenyl)-3-(4-hydroxyphenyl)propan-1-one

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