Acacetin

Base Information

• Chemical Name: Acacetin
• CAS No.: 480-44-4
• Molecular Formula: C16H12O5
• Molecular Weight: 284.268
• Hs Code.: 29329990
• European Community (EC) Number: 207-552-3
• UNII: KWI7J0A2CC
• ChEMBL ID: CHEMBL243664
• DSSTox Substance ID: DTXSID00197383
• Metabolomics Workbench ID: 23553
• Nikkaji Number: J6.166B
• NSC Number: 76061
• Pharos Ligand ID: BGGK66ZTSW9U
• Wikidata: Q2822213
• Wikipedia: Acacetin
• Mol file: 480-44-4.mol

Synonyms:acacetin

Chemical Property of Acacetin

Chemical Property:

• Appearance/Colour: Pale-yellow needles
• Vapor Pressure: 2.25E-11mmHg at 25°C
• Melting Point: 260-265 °C
• Refractive Index: 1.668
• Boiling Point: 518.6 °C at 760 mmHg
• PKA: 6.51±0.40(Predicted)
• Flash Point: 198.2 °C
• PSA: 79.90000
• Density: 1.42 g/cm³
• LogP: 2.87980
• Storage Temp.: 2-8°C
• Solubility.: DMSO (Slightly), Methanol (Very Slightly, Heated)
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 284.06847348
• Heavy Atom Count: 21
• Complexity: 424

Purity/Quality:

98% ^*data from raw suppliers

Acacetin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC=C(C=C1)C2=CC(=O)C3=C(C=C(C=C3O2)O)O
• Description: Acacetin is an O-methylated flavone found in various plants. It is reported to demonstrate spasmolytic, antinociceptive, anti-inflammatory, and antioxidant activity in various research models.
• Uses: VEGF expression inhibitor and tumor angiogenesis. A flavonoid with antiaggregatory activity in human blood.

Technology Process of Acacetin

There total 59 articles about Acacetin 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%

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

Guidance literature:

With sodium methylate; In methanol; at 20 ℃; for 1h;

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

Reference yield: 87.0%

5-hydroxy-4'-methoxy-7-[(2-O-α-L-rhamnopyranosyl-β-D-glucopyranosyl)oxy]flavone (20633-93-6) → 5,7-dihydroxy-2-(4'-methoxyphenyl)-4H-1-benzopyran-4-one (480-44-4)

Guidance literature:

With ethanol; sulfuric acid; for 2h; Reflux;

DOI:10.1016/j.molcatb.2016.03.001

Reference yield: 81.0%

3,5-dihydroxyphenol (108-73-6) + ethyl 4-methoxybenzoylacetate (2881-83-6) → 5,7-dihydroxy-2-(4'-methoxyphenyl)-4H-1-benzopyran-4-one (480-44-4)

Guidance literature:

for 0.0583333h; microwave irradiation;

DOI:10.1021/jo048685z

upstream raw materials:

3,5-dihydroxyphenol

methyl 3-(4-methoxybenzoyl)acetate

5,7-dihydroxy-2-(4-methoxyphenyl)chroman-4-one

5,7-diacetoxy-2-(4-methoxy-phenyl)-chroman-4-one

Downstream raw materials:

acacetin diacetate

C₁₈H₁₆O₅

C₂₃H₁₆O₆

5-hydroxy-4'-methoxyflavone 7-O-β-D-galactopyranoside tetraacetate

Refernces

• 1、 Markham et al.. "-". . p. 2875,2876. Retrieved 1972.
• 2、 Kurkina,Khusainova,Daeva,Kadentsev. "Flavonoids from tanacetum vulgare flowers". . p. 284 - 285. Retrieved 2011.
• 3、 Olennikov,Kashchenko. "New C,O-Glycosylflavones from the Genus Silene". . p. 1026 - 1034. Retrieved 2020/11/05.
• 4、 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.