Apigenin triacetate

Base Information

• Chemical Name: Apigenin triacetate
• CAS No.: 3316-46-9
• Molecular Formula: C21H16 O8
• Molecular Weight: 396.353
• Hs Code.: 2915390090
• UNII: 6LQX84KDOB
• DSSTox Substance ID: DTXSID70186805
• Nikkaji Number: J45.896A
• Wikidata: Q27163976
• ChEMBL ID: CHEMBL3039042
• Mol file: 3316-46-9.mol

Synonyms:Apigenin triacetate;3316-46-9;Triacetyl apigenin;APIGENINTRIACETATE;4',5,7-Triacetoxy flavone;[4-(5,7-diacetyloxy-4-oxochromen-2-yl)phenyl] acetate;UNII-6LQX84KDOB;6LQX84KDOB;FLAVONE, 4',5,7-TRIHYDROXY-, TRIACETATE;4',5,7-Triacetoxyflavone;4H-1-Benzopyran-4-one, 5,7-bis(acetyloxy)-2-(4-acetyloxy)phenyl-;C21H16O5;4H-1-Benzopyran-4-one, 5,7-bis(acetyloxy)-2-[4-(acetyloxy)phenyl]-;TRIACETYLAPIGENIN;Spectrum2_000291;Spectrum3_001883;BSPBio_003386;SPBio_000222;SCHEMBL1676023;CHEMBL3039042;CHEBI:92205;KBio3_002889;DTXSID70186805;CCG-39849;SDCCGMLS-0066423.P001;NCGC00178101-01;LS-69049;BRD-K12057390-001-01-7;Q27163976;5-(Acetyloxy)-2-[4-(acetyloxy)phenyl]-4-oxo-4H-chromen-7-yl acetate #

Chemical Property of Apigenin triacetate

Chemical Property:

• Vapor Pressure: 5.55E-13mmHg at 25°C
• Boiling Point: 569.5°Cat760mmHg
• Flash Point: 249.6°C
• PSA: 109.11000
• Density: 1.356g/cm³
• LogP: 3.23590
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 7
• Exact Mass: 396.08451746
• Heavy Atom Count: 29
• Complexity: 704

Purity/Quality:

99% ^*data from raw suppliers

ApigeninTriacetate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OC1=CC=C(C=C1)C2=CC(=O)C3=C(O2)C=C(C=C3OC(=O)C)OC(=O)C
• Uses: Apigenin Triacetate is an intermediate in synthesizing Isorhoifolin (I819700), a naturally occurring flavonoid that was shown to exhibit potential antidiabetic, antihyperlipidemic and antioxidant effects.

Technology Process of Apigenin triacetate

There total 7 articles about Apigenin triacetate 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: 94.0%

5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one (520-36-5) + acetic anhydride (108-24-7) → apigenin triacetate (3316-46-9)

Guidance literature:

With pyridine; at 70 ℃; for 6h;

DOI:10.1016/j.bmc.2014.04.016

Reference yield:

naringin (10236-47-2) → apigenin triacetate (3316-46-9)

Guidance literature:

Multi-step reaction with 3 steps

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

2: iodine; pyridine / 24 h / 90 °C

3: pyridine; dmap / 6 h / 80 °C

With pyridine; dmap; sulfuric acid; iodine; In water;

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

Reference yield:

4',5,7-triacetoxyflavan-4-one (73111-01-0) → apigenin triacetate (3316-46-9)

Guidance literature:

With tetrachloromethane; N-Bromosuccinimide;

DOI:10.1021/jo01086a609

upstream raw materials:

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

acetic anhydride

5,7-Dihydroxy-2-(4-hydroxy-phenyl)-chroman-4-on

potassium acetate

Downstream raw materials:

5,7-diacetoxy-4'-hydroxyflavone

7-((4-fluorobenzyl)oxy)-5-hydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one

7-(tert-butoxy)-5-hydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one

5-hydroxy-2-(4-hydroxyphenyl)-7-morpholino-4H-chromen-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、 Li, Yue-Qing,Yang, Fei,Wang, Liu,Cao, Zhi,Han, Tian-Jiao,Duan, Zhe-Ang,Li, Zhen,Zhao, Wei-Jie. "Phosphoramidate protides of five flavones and their antiproliferative activity against HepG2 and L-O2 cell lines". . p. 196 - 208. Retrieved 2016/05/02.