Acacetin diacetate

Base Information

• Chemical Name: Acacetin diacetate
• CAS No.: 5892-39-7
• Molecular Formula: C₂₀H₁₆O₇
• Molecular Weight: 368.343
• ChEMBL ID: CHEMBL1566650
• DSSTox Substance ID: DTXSID001346782
• Wikidata: Q63395517
• Mol file: 5892-39-7.mol

Synonyms:ACACETIN DIACETATE;5892-39-7;KBio1_001498;Spectrum_000643;SpecPlus_000458;Spectrum2_000192;Spectrum3_000194;Spectrum4_001511;Spectrum5_000301;BSPBio_001747;KBioGR_002201;KBioSS_001123;SPECTRUM200833;DivK1c_006554;SPBio_000143;CHEMBL1566650;SCHEMBL10026579;KBio2_001123;KBio2_003691;KBio2_006259;KBio3_001247;DTXSID001346782;CCG-38398;SDCCGMLS-0066375.P001;NCGC00095492-01;NCGC00095492-02;NCGC00179038-01;SR-05000002622;SR-05000002622-1;Q63395517

Chemical Property of Acacetin diacetate

Chemical Property:

• Vapor Pressure: 5.44E-12mmHg at 25°C
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 6
• Exact Mass: 368.08960285
• Heavy Atom Count: 27
• Complexity: 618

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(=O)OC1=CC2=C(C(=C1)OC(=O)C)C(=O)C=C(O2)C3=CC=C(C=C3)OC

Technology Process of Acacetin diacetate

There total 8 articles about Acacetin diacetate 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: 100.0%

trimethoxonium tetrafluoroborate (420-37-1) + 5,7-diacetoxy-4'-hydroxyflavone (132351-62-3) → acacetin diacetate (5892-39-7)

Guidance literature:

With N,N,N',N'-tetramethyl-1,8-diaminonaphthalene; In dichloromethane; at 20 ℃; for 6h; Molecular sieve;

DOI:10.3987/COM-18-S(F)17

Reference yield:

5,7-dihydroxy-2-(4'-methoxyphenyl)-4H-1-benzopyran-4-one (480-44-4) + acetic anhydride (108-24-7) → acacetin diacetate (5892-39-7)

Guidance literature:

at 140 ℃; for 1h;

DOI:10.1016/S0031-9422(00)80758-X

Reference yield:

naringin (10236-47-2) → acacetin diacetate (5892-39-7)

Guidance literature:

Multi-step reaction with 5 steps

1: sulfuric acid / water / 2 h / 121 °C

2: iodine; pyridine / 24 h / 90 °C

3: pyridine; dmap / 6 h / 80 °C

4: Candida antarctica lipase B / isopropyl alcohol; tetrahydrofuran / 40 h / 22 °C / Enzymatic reaction

5: N,N,N',N'-tetramethyl-1,8-diaminonaphthalene / dichloromethane / 6 h / 20 °C / Molecular sieve

With pyridine; dmap; Candida antarctica lipase B; sulfuric acid; iodine; N,N,N',N'-tetramethyl-1,8-diaminonaphthalene; In tetrahydrofuran; dichloromethane; water; isopropyl alcohol;

DOI:10.3987/COM-18-S(F)17

upstream raw materials:

5,7-dihydroxy-2-(4'-methoxyphenyl)-4H-1-benzopyran-4-one

acetic anhydride

5-hydroxy-4'-methoxy-7-[(2-O-α-L-rhamnopyranosyl-β-D-glucopyranosyl)oxy]flavone

naringin

Downstream raw materials:

5,7-dihydroxy-2-(4'-methoxyphenyl)-4H-1-benzopyran-4-one

Refernces

• 1、 Fujita, Rie,Hanaya, Kengo,Higashibayashi, Shuhei,Mandal, Susanta,Shoji, Mitsuru,Sugai, Takeshi. "Site-selective synthesis of acacetin and genkwanin through lipase-catalyzed deacetylation of apigenin 5,7-diacetate and subsequent methylation". . p. 638 - 648. Retrieved 2019/07/31.
• 2、 Thusoo,Raina,Ahmed. "Flavonoids and other constituents of Indigofera hetrantha". . p. 1007 - 1008. Retrieved 2007/10/02.