8-Methoxycirsilineol

Base Information

• Chemical Name: 8-Methoxycirsilineol
• CAS No.: 16520-78-8
• Molecular Formula: C19H18 O8
• Molecular Weight: 374.347
• NSC Number: 654971
• UNII: 72Y87O5H1X
• DSSTox Substance ID: DTXSID40937048
• Nikkaji Number: J61.266I
• Wikidata: Q27266108
• Metabolomics Workbench ID: 24558
• ChEMBL ID: CHEMBL74272
• Mol file: 16520-78-8.mol

Synonyms:4',5-dihydroxy-3',6,7,8-tetramethoxyflavone;8-methoxycirsilineol

Chemical Property of 8-Methoxycirsilineol

Chemical Property:

• Vapor Pressure: 1.89E-16mmHg at 25°C
• Melting Point: 192 °C
• Boiling Point: 629.7°C at 760 mmHg
• PKA: 6.82±0.40(Predicted)
• Flash Point: 228.1°C
• PSA: 107.59000
• Density: 1.375g/cm³
• LogP: 2.90560
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 5
• Exact Mass: 374.10016753
• Heavy Atom Count: 27
• Complexity: 564

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C=CC(=C1)C2=CC(=O)C3=C(C(=C(C(=C3O2)OC)OC)OC)O)O

Technology Process of 8-Methoxycirsilineol

There total 10 articles about 8-Methoxycirsilineol 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: 60.0%

3′-methoxy-4′-hydroxy-5,6,7,8-tetramethoxyflavone (34810-62-3) → 8-methoxycirsilineol (16520-78-8)

Guidance literature:

With aluminum (III) chloride; In acetonitrile; at 60 ℃; for 3h;

Reference yield: 47.0%

4'-benzyloxy-3',5,6,7,8-pentamethoxyflavone (29201-97-6) → 8-methoxycirsilineol (16520-78-8)

Guidance literature:

With aluminum (III) chloride; ethanethiol; In dichloromethane; regioselective reaction;

DOI:10.1016/j.tetlet.2018.03.064

Reference yield: 43.0%

4'-benzyloxy-3',5,6,7,8-pentamethoxyflavone (29201-97-6) → 8-methoxycirsilineol (16520-78-8) + 4'-benzyloxy-5-hydroxy-3',6,7,8-tetramethoxyflavone (1350827-34-7)

Guidance literature:

4'-benzyloxy-3',5,6,7,8-pentamethoxyflavone; With boron trichloride; In dichloromethane; toluene; at -15 - 20 ℃; for 12h; Inert atmosphere;

With water; sodium hydroxide; In dichloromethane; toluene; at 20 ℃; for 1h;

DOI:10.1016/j.bmc.2011.10.001

upstream raw materials:

4'-benzyloxy-3',5,6,7,8-pentamethoxyflavone

(1H-benzo[d][1,2,3]triazol-1-yl)(4-(benzyloxy)-3-methoxyphenyl)methanone

C₂₇H₂₈O₉

3-methoxy-4-hydroxybenzoic acid

Downstream raw materials:

5,8,4'-trihydroxy-6,5,3'-trimethoxyflavone

demethylthymonin

nobiletin

5,6,4'-trihydroxy-7,8,3'-trimethoxyflavone

Refernces

• 1、 Asakawa, Tomohiro,Sagara, Hiroto,Kanakogi, Masaki,Hiza, Aiki,Tsukaguchi, Yuta,Ogawa, Takahiro,Nakayama, Miho,Ouchi, Hitoshi,Inai, Makoto,Kan, Toshiyuki. "Practical Synthesis of Polymethylated Flavones: Nobiletin and Its Desmethyl Derivatives". . p. 595 - 602. Retrieved 2019/04/01.
• 2、 Oshitari, Tetsuta,Okuyama, Yuji,Miyata, Yoshiki,Kosano, Hiroshi,Takahashi, Hideyo,Natsugari, Hideaki. "B-Ring-modified and/or 5-demethylated nobiletin congeners: Inhibitory activity against pro-MMP-9 production". experimental part. p. 7085 - 7092. Retrieved 2012/01/02.