2-(Acetyloxy)-4-(3,7-bis(acetyloxy)-5-hydroxy-4-oxo-4H-chromen-2-yl)phenyl acetate

Base Information

• Chemical Name: 2-(Acetyloxy)-4-(3,7-bis(acetyloxy)-5-hydroxy-4-oxo-4H-chromen-2-yl)phenyl acetate
• CAS No.: 7251-37-8
• Molecular Formula: C23H18O11
• Molecular Weight: 470.389
• NSC Number: 61836
• UNII: LFS2KN7A3L
• DSSTox Substance ID: DTXSID60222827
• Nikkaji Number: J2.595.231F
• Wikidata: Q83101171
• ChEMBL ID: CHEMBL521171
• Mol file: 7251-37-8.mol

Synonyms:7251-37-8;LFS2KN7A3L;NSC61836;2-(Acetyloxy)-4-(3,7-bis(acetyloxy)-5-hydroxy-4-oxo-4H-chromen-2-yl)phenyl acetate;Quercetin 3,3',4',7-tetraacetate;UNII-LFS2KN7A3L;NSC 61836;NSC-61836;4-(3,7-diacetoxy-5-hydroxy-4-oxo-4H-chromen-2-yl)-1,2-phenylene diacetate;SMR000387027;Oprea1_131650;MLS001049033;MLS003901458;CHEMBL521171;DTXSID60222827;HMS2271C07;STL564428;3,3',4',7-Tetra-O-acetylquercetin;AKOS030487685;NCGC00246188-01;QUERCETIN, 3,3',4',7-TETRAACETATE;[2-acetoxy-4-(3,7-diacetoxy-5-hydroxy-4-oxo-chromen-2-yl)phenyl] acetate;FLAVONE, 3,3',4',5,7-PENTAHYDROXY-, 3,3',4',7-TETRAACETATE;2-[3,4-bis(acetyloxy)phenyl]-5-hydroxy-4-oxo-4H-chromene-3,7-diyl diacetate;3,7-BIS(ACETYLOXY)-2-(3,4-BIS(ACETYLOXY)PHENYL)-5-HYDROXY-4H-1-BENZOPYRAN-4-ONE;4H-1-BENZOPYRAN-4-ONE, 3,7-BIS(ACETYLOXY)-2-(3,4-BIS(ACETYLOXY)PHENYL)-5-HYDROXY-;7-(acetyloxy)-2-[3,4-bis(acetyloxy)phenyl]-5-hydroxy-4-oxo-4H-chromen-3-yl acetate

Chemical Property of 2-(Acetyloxy)-4-(3,7-bis(acetyloxy)-5-hydroxy-4-oxo-4H-chromen-2-yl)phenyl acetate

Chemical Property:

• Vapor Pressure: 6.47E-18mmHg at 25°C
• Boiling Point: 657.9°C at 760 mmHg
• Flash Point: 226.6°C
• Density: 1.5g/cm³
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 9
• Exact Mass: 470.08491139
• Heavy Atom Count: 34
• Complexity: 891

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OC1=C(C=C(C=C1)C2=C(C(=O)C3=C(C=C(C=C3O2)OC(=O)C)O)OC(=O)C)OC(=O)C

Technology Process of 2-(Acetyloxy)-4-(3,7-bis(acetyloxy)-5-hydroxy-4-oxo-4H-chromen-2-yl)phenyl acetate

There total 6 articles about 2-(Acetyloxy)-4-(3,7-bis(acetyloxy)-5-hydroxy-4-oxo-4H-chromen-2-yl)phenyl acetate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

3,5,7-triacetoxy-2-(3,4-diacetoxy-phenyl)-chromen-4-one (1064-06-8) → 4-(3,7-diacetoxy-5-hydroxy-4-oxo-4H-chromen-2-yl)-1,2-phenylene diacetate (7251-37-8)

Guidance literature:

With boron trifluoride diethyl etherate; In 1,4-dioxane; at 80 ℃; for 6h;

DOI:10.1080/09168451.2018.1467263

Reference yield: 75.0%

quercetol (117-39-5,74893-81-5) + acetic anhydride (108-24-7) → 4-(3,7-diacetoxy-5-hydroxy-4-oxo-4H-chromen-2-yl)-1,2-phenylene diacetate (7251-37-8)

Guidance literature:

With pyridine; In dichloromethane; at 20 ℃; for 3h; regioselective reaction;

DOI:10.3390/molecules15074722

Reference yield: 55.0%

quercetol (117-39-5,74893-81-5) + acetic anhydride (108-24-7) → 4-(3,7-diacetoxy-5-hydroxy-4-oxo-4H-chromen-2-yl)-1,2-phenylene diacetate (7251-37-8) + 3,5,7-triacetoxy-2-(3,4-diacetoxy-phenyl)-chromen-4-one (1064-06-8)

Guidance literature:

With triethylamine; In N,N-dimethyl-formamide; at 20 ℃; for 5h;

upstream raw materials:

acetic anhydride

quercetol

taxifolin

3,5,7-triacetoxy-2-(3,4-diacetoxy-phenyl)-chromen-4-one

Downstream raw materials:

C₂₆H₂₂O₁₁

3,3′,4′,7-tetraacetoxyflavone

3,7,3',4'-tetrahydroxyflavone

3,3',4'-Triaacetoxy-5,7-dihydroxyflavone

Refernces

• 1、 Tsunekawa, Ryuji,Hanaya, Kengo,Higashibayashi, Shuhei,Sugai, Takeshi. "Synthesis of fisetin and 2′,4′,6′-trihydroxydihyrochalcone 4′-O-β-neohesperidoside based on site-selective deacetylation and deoxygenation". . p. 1316 - 1322. Retrieved 2018/07/29.
• 2、 Kiehlmann, Eberhard,Szczepina, Monica G.. "Epimerization, transacylation and bromination of dihydroquercetin acetates; Synthesis of 8-bromodihydroquercetin". experimental part. p. 492 - 498. Retrieved 2012/05/20.