Spinacetin

Base Information

• Chemical Name: Spinacetin
• CAS No.: 3153-83-1
• Molecular Formula: C17H14 O8
• Molecular Weight: 346.293
• Hs Code.: 2914509090
• UNII: 5FBC7BNF1S
• DSSTox Substance ID: DTXSID10185433
• Nikkaji Number: J13.002H
• Wikipedia: Spinacetin
• Wikidata: Q3493504
• Metabolomics Workbench ID: 26078
• Mol file: 3153-83-1.mol

Synonyms:3,4',5,7-tetrahydroxy-3',6-dimethoxyflavone;3,5,7-trihydroxy-2-(4-hydroxy-3-methoxyphenyl)-6-methoxychromen-4-one;quercetagetin 3',6-dimethyl ether;spinacetin

Chemical Property of Spinacetin

Chemical Property:

• Melting Point: 228-232 °C
• Boiling Point: 642.9±55.0 °C(Predicted)
• PKA: 6.29±0.40(Predicted)
• PSA: 129.59000
• Density: 1.591±0.06 g/cm3(Predicted)
• LogP: 2.29960
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 3
• Exact Mass: 346.06886740
• Heavy Atom Count: 25
• Complexity: 547

Purity/Quality:

99%, ^*data from raw suppliers

Spinacetin ≥98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C=CC(=C1)C2=C(C(=O)C3=C(O2)C=C(C(=C3O)OC)O)O)O

Technology Process of Spinacetin

There total 16 articles about Spinacetin 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: 76.0%

7-Benzyloxy-2-(4-benzyloxy-3-methoxy-phenyl)-3,5-dihydroxy-6-methoxy-chromen-4-one (188927-59-5) → spinacetin (3153-83-1)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; ethyl acetate; Ambient temperature;

DOI:10.1248/cpb.45.446

Reference yield:

spinacetin 7-O-(6''-O-caffeoyl)-β-D-glucopyranoside → spinacetin (3153-83-1) + D-glucose (50-99-7) + caffeic acid (331-39-5,501-16-6)

Guidance literature:

With trifluoroacetic acid; at 110 ℃; for 2h;

DOI:10.1007/s10600-015-1498-y

Reference yield:

3-methoxy-4-benzyloxybenzoyl chloride (1486-52-8) → spinacetin (3153-83-1)

Guidance literature:

Multi-step reaction with 8 steps

1: pyridine / 2 h / 70 - 80 °C

2: KOH / pyridine / 80 °C

3: 97 percent / conc. H₂SO₄, acetic acid / 1 h / 50 °C

4: 56 percent / dimethyldioxirane / acetone / 0 °C

5: 98 percent / K₂CO₃ / acetone / Heating

6: 85 percent / AlCl₃ / acetonitrile / 0.5 h / Ambient temperature

7: 85 percent / K₂CO₃ / methanol / 1.5 h / Heating

8: 76 percent / H₂ / 10percent Pd/C / methanol; ethyl acetate / Ambient temperature

With pyridine; potassium hydroxide; aluminium trichloride; sulfuric acid; hydrogen; 3,3-dimethyldioxirane; potassium carbonate; acetic acid; palladium on activated charcoal; In pyridine; methanol; ethyl acetate; acetone; acetonitrile;

DOI:10.1248/cpb.45.446

upstream raw materials:

methyl iodide

7-Benzyloxy-2-(4-benzyloxy-3-methoxy-phenyl)-3,5-dihydroxy-6-methoxy-chromen-4-one

3-methoxy-4-benzyloxybenzoyl chloride

1-(2,4-Bis-benzyloxy-3,6-dimethoxy-phenyl)-ethanone

Downstream raw materials:

3,5,6,7,3',4'-Hexamethoxyflavon

Refernces

• 1、 Horie, Tokunaru,Shibata, Kenichi,Yamashita, Kazuyo,Kawamura, Yasuhiko,Tsukayama, Masao. "Studies of the selective O-alkylation and dealkylation of flavonoids. XXII. A convenient method for synthesizing 3,5,7-trihydroxy-6-methoxyflavones". . p. 446 - 451. Retrieved 2007/10/03.
• 2、 Miski, Mahmut,Gage, Douglas A.,Mabry, Tom J.. "QUERCETAGETIN 6,7,4'-TRIMETHYL ETHER AND 3-SULPHATE FROM DECACHAETA HAENKEANA". . p. 3078 - 3080. Retrieved 2007/10/02.