23130-22-5

Basic information

• Product Name: SCUTELLAREIN-7-METHYL ETHER
• Synonyms: SORBIFOLIN;SCUTELLAREIN-7-METHYL ETHER;5,6-Dihydroxy-2-(4-hydroxyphenyl)-7-methoxy-4H-1-benzopyran-4-one;Sorbifolin【flavone】
• CAS NO: 23130-22-5
• Molecular Formula: C₁₆H₁₂O₆
• Molecular Weight: 300.26
• Product Categories: Miscellaneous Natural Products
• Mol File: 23130-22-5.mol

Chemical Properties

• Boiling Point: 601.7°Cat760mmHg
• Flash Point: 230.2°C
• Appearance: /
• Density: 1.512g/cm³
• Vapor Pressure: 4.5E-15mmHg at 25°C
• Refractive Index: 1.697
• CAS DataBase Reference: SCUTELLAREIN-7-METHYL ETHER(CAS DataBase Reference)
• NIST Chemistry Reference: SCUTELLAREIN-7-METHYL ETHER(23130-22-5)
• EPA Substance Registry System: SCUTELLAREIN-7-METHYL ETHER(23130-22-5)

Safety Data

• Hazardous Substances Data: 23130-22-5(Hazardous Substances Data)

Usage

InChI:InChI=1/C16H12O6/c1-21-13-7-12-14(16(20)15(13)19)10(18)6-11(22-12)8-2-4-9(17)5-3-8/h2-7,17,19-20H,1H3

Upstream product

• 1180-46-7 4,5,6,7-tetra-O-acetylflavone 
• 33507-92-5 7-(benzyloxy)-5,6-diacetoxy-2-(4-acetoxyphenyl)-4H-chromen-4-one 
• 33507-93-6 7-hydroxy-5,6-diacetoxy-2-(4'-acetoxyphenyl)-4H-1-benzopyran-4-one 
• 29528-35-6 7-methoxy-5,6-diacetoxy-2-(4'-acetoxyphenyl)-4H-1-benzopyran-4-one 
• 529-53-3 scutellarein 
• 27740-01-8 scutellarin 
• 89647-63-2 scutellarin-6-O-glucoside-7-methyl ether 

Downstream Products

• 29528-35-6 7-methoxy-5,6-diacetoxy-2-(4'-acetoxyphenyl)-4H-1-benzopyran-4-one 

Relevant articles and documents

Synthesis and biological evaluation of scutellarein alkyl derivatives as preventing neurodegenerative agents with improved lipid soluble properties

Background: Exogenous antioxidants are considered as a promising therapeutic approach to treat neurodegenerative diseases since they could prevent and/or minimize the neuronal damage by oxidation. Objective: Three series of lipophilic compounds structurally based on scutellarein (2), which is one metabolite of scutellarin (1) in vivo, have been designed and synthesized. Methods: Their antioxidant activity was evaluated by detecting the 2-thiobarbituric acid reactive substance (TBARS) produced in the ferrous salt/ascorbate-induced autoxidation of lipids, which were present in microsomal membranes of rat hepatocytes. The lipophilicity of these compounds indicated as partition coefficient between n-octanol and buffer was investigated by ultraviolet (UV) spectrophotometer. Results: This study indicated that compound 5e which had a benzyl group substituted at the C4'-OH position showed a potent antioxidant activity and good lipophilicity. Conclusion: 5e could be an effective candidate for preventing or reducing the oxidative status associated with the neurodegenerative processes.

Synthesis and biological evaluation of methylated scutellarein analogs based on metabolic mechanism of scutellarin in vivo

Scutellarin (1) could be hydrolyzed into scutellarein (2) in vivo and then converted into methylated, sulfated and glucuronidated forms. In order to investigate the biological activities of these methylated metabolites, eight methylated analogs of scutellarein (2) were synthesized via semi-synthetic methods. The antithrombotic activities of these compounds were evaluated through the analyzation of prothrombin time (PT), activated partial thromboplastin time (APTT), thrombin time (TT) and fibrinogen (FIB). Their antioxidant activities were assessed by measuring their scavenging capacities toward 1,1-diphenyl-2-picrylhydrazyl radical (DPPH) and the ability to protect PC12 cells against H2O2-induced cytotoxicity. Furthermore, the physicochemical properties of these compounds including aqueous solubility and lipophilicity were also investigated. The results showed that 6-O-methylscutellarein (5) demonstrated potent antithrombotic activity, stronger antioxidant activity and balanced solubility and permeability compared with scutellarin (1), which warrants further development of 5 as a promising lead for the treatment of ischemic cerebrovascular disease.

Lipids and flavonoids from Sesamum laciniatum Klein

From the aerial parts of Sesamum laciniatum eight methyl esters of fatty acids and a new compound 7-O-methylscutellarein-6-O-glucoside (1), have been isolated.Besides, pentatriacontane, fatty acid esters of β-sitosterol and β-amyrin, β-sitosterol and its glucoside, and a partially characterised diglucoside of 7-O-methylscutellarein are also isolated.

SORBIFOLIN 6-GALACTOSIDE FROM GARCINIA ANDAMANICA

A new flavone glycoside, sorbifolin 6-galactoside, has been isolated from the leaves of Garcinia andamanica along with the known scutellarein 7-diglicoside.Their structures were establishes using spectroscopic and chemical evidence.Key Word Index - Garcinia andamanica; Guttifereae; sorbifolin 6-galactoside; scutellarein 7-diglucoside.