1180-46-7

Basic information

• Product Name: 4',5,6,7-Tetrahydroxyflavone tetraacetate
• Synonyms: 4',5,6,7-Tetrahydroxyflavone tetraacetate;[4-(5,6,7-triacetyloxy-4-oxochromen-2-yl)phenyl] acetate
• CAS NO: 1180-46-7
• Molecular Formula: C₂₃H₁₈O₁₀
• Molecular Weight: 454.38302
• Mol File: 1180-46-7.mol

Chemical Properties

• Boiling Point: 633.8°Cat760mmHg
• Flash Point: 274.2°C
• Appearance: /
• Density: 1.377g/cm³
• Vapor Pressure: 5.72E-16mmHg at 25°C
• Refractive Index: 1.578
• CAS DataBase Reference: 4',5,6,7-Tetrahydroxyflavone tetraacetate(CAS DataBase Reference)
• NIST Chemistry Reference: 4',5,6,7-Tetrahydroxyflavone tetraacetate(1180-46-7)
• EPA Substance Registry System: 4',5,6,7-Tetrahydroxyflavone tetraacetate(1180-46-7)

Safety Data

• Hazardous Substances Data: 1180-46-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
4',5,6,7-Tetrahydroxyflavone tetraacetate is used as a therapeutic agent for its antioxidant properties, which protect cells from oxidative damage. It is also utilized for its anti-inflammatory effects, which may help in managing inflammation-related conditions.
Used in Cosmetic Industry:
In cosmetics, 4',5,6,7-Tetrahydroxyflavone tetraacetate serves as an active ingredient due to its antioxidant capabilities, helping to preserve the shelf life of products and protect the skin from environmental stressors. Its anti-inflammatory properties can also contribute to soothing skincare formulations.
Used in Anticancer Research:
4',5,6,7-Tetrahydroxyflavone tetraacetate is studied as a potential cancer treatment, given its ability to target various cellular pathways involved in tumor growth and progression. It is being investigated for its efficacy against different types of cancer, including its potential to enhance the effectiveness of conventional chemotherapy.
Used in Cardiovascular Disease Prevention:
4',5,6,7-Tetrahydroxyflavone tetraacetate is being explored for its potential role in preventing cardiovascular diseases, capitalizing on its antioxidant properties to combat the oxidative stress that contributes to the development of such conditions.
Used in Neurodegenerative Disorder Management:
4',5,6,7-Tetrahydroxyflavone tetraacetate is also considered for its potential to mitigate neurodegenerative disorders, leveraging its antioxidant and anti-inflammatory properties to protect neurons and slow disease progression.

InChI:InChI=1/C23H18O10/c1-11(24)29-16-7-5-15(6-8-16)18-9-17(28)21-19(33-18)10-20(30-12(2)25)22(31-13(3)26)23(21)32-14(4)27/h5-10H,1-4H3

Upstream product

• 529-53-3 scutellarein 
• 108-24-7 acetic anhydride 
• 21967-41-9 baicalin 
• 27740-01-8 scutellarin 
• 1168-42-9 5,6,7,4'-tetramethoxyflavone 
• 3877-67-6 1-(6-hydroxy-2,3,4-trimethoxyphenyl)-3-(4-methoxyphenyl)prop-2-en-1-one 
• 22248-14-2 6-hydroxy-2,3,4-trimethoxyacetophenone 
• 642-71-7 3,4,5-trimethoxyphenol 

Downstream Products

• 1374218-56-0 5,6,7,4'-tetraacetoxy-8-nitroflavone 
• 1374218-58-2 C₁₉H₁₅NO₈ 
• 1373921-90-4 5,6,7,4'-tetraacetoxy-8-chloroflavone 
• 1373922-27-0 5,6,7,4'-tetraacetoxy-3-bromoflavone 
• 1373922-21-4 5,6,7,4'-tetraacetoxy-8-bromoflavone 
• 1374218-52-6 5,6,7,4'-tetraacetoxy-8-iodoflavone 
• 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 
• 26046-94-6 plantaginin 
• 676536-34-8 scutellarein 7-O-glucuronopyranoside 
• 27740-01-8 scutellarin 
• 119262-68-9 scutellarein 7-O-β-D-glucuronopyranoside methyl ester 
• 54917-66-7 5,6,4'-triacetoxy-7-hydroxyflavon-7-O-(2,3,4-tri-O-acetyl-β-D-glucopyranosiduronsauremethyl ester) 
• 529-53-3 scutellarein 

Relevant articles and documents

Synthesis of scutellarein derivatives with a long aliphatic chain and their biological evaluation against human cancer cells

Scutellarin is the major active flavonoid extracted from the traditional Chinese herbal medicine Erigeron breviscapus (Vant.) Hand-Mazz., which is widely used in China. Recently, accumulating evidence has highlighted the potential role of scutellarin and its main metabolite scutellarein in the treatment of cancer. To explore novel anticancer agents with high efficiency, a series of new scutellarein derivatives with a long aliphatic chain were synthesized, and the antiproliferative activities against Jurkat, HCT-116 and MDA-MB-231 cancer cell lines were assessed. Among them, compound 6a exhibited the strongest antiproliferative effects on Jurkat (IC50 = 1.80 μM), HCT-116 (IC50 = 11.50 μM) and MDA-MB-231 (IC50 = 53.91 μM). In particular, 6a even showed stronger antiproliferative effects than the positive control NaAsO2 on Jurkat and HCT-116 cell lines. The results showed that a proper long aliphatic chain enhanced the antiproliferative activity of scutellarein.

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.

Scutellarin aglycone ether derivative and preparation method and application thereof

The invention discloses a scutellarin aglycone ether derivative (I) and a preparation method and application thereof in anti-tumor drugs. The compound is characterized in that 7-hydroxyl of the scutellarin aglycone and an aliphatic hydrocarbon group with more than one C form ether, and 6-hydroxyl and 4'-hydroxyl are modified by acetoxy. The compound is prepared based on the raw material scutellarin and is obtained through two steps of reaction, thereby being easy to prepare. Compared with scutellarin and scutellarin aglycone, the compound has better anti-tumor activity and is more stable. Thescutellarin aglycone ether derivative (I) can be used for resisting tumors. The formula is shown in the description.

Preparation of 5, 6, 4 '-three hydroxy flavone-7-0-D-glucuro method

The invention relates to the field of drug synthesis and discloses a method for preparing 5,6,4'-trihydroxy flavone-7-0-D-glucuronic acid. The method is characterized by taking 5,6,7,4'-tetrahydroxy flavone as a raw material, adopting a brand-new syntheti

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.

METHOD FOR PREPARING 5,6,4'-TRIHYDROXYFLAVONE-7-0-D-GLUCURONIC ACID

The present invention relates to the field of drug synthesis. Disclosed is a method for preparing 5,6,4'-trihydroxyflavone-7-O-D-glucuronic acid. The method for preparing 5,6,4'-trihydroxyflavone-7-O-D-glucuronic acid of the present invention uses 5,6,7,4'-tetrahydroxyflavone as a raw material and adopts a new synthetic route to obtain high-purity 5,6,4'-trihydroxyflavone-7-O-D-glucuronic acid through an acylation reaction, a glycosylation reaction, and two-step hydrolysis. The preparing method of the present invention has a short synthetic route, low cost, and high reaction yield, the product is easy for purification, and the method is applicable to industrial production of 5,6,4'-trihydroxyflavone-7-O-D-glucuronic acid.

METHOD FOR PREPARING HIGH PURITY SCUTELLARIN AGLYCONE

Provided is a method for preparing scutellarin aglycone. In the method, 5,6,7,4'-tetramethoxy flavone is used as raw material, and high purity scutellarin aglycone is obtained through four steps of demethylation, acylation, hydrolyzation, and refinement. The preparing method is characterized by a low synthesis cost, a short line, and a high reaction yield, and the product is easily purified, can implement industrialized production, and has a desired industrial application prospect.

An improved synthesis of scutellarin-7-O-glucuronid

An eight-step synthesis of scutellarin-7-O-glucuronide via a novel preparation of the intermediate 5,6,7,4′-trimethoxyflavone from a chalcone derivative is described. The conditions of certain steps were studied and optimised to give an overall yield of 20%.

Design, synthesis and biological evaluation of glucose-containing scutellarein derivatives as neuroprotective agents based on metabolic mechanism of scutellarin in vivo

Based on metabolic mechanism of scutellarin in vivo that scutellarin could be hydrolyzed into scutellarein by β-glucuronide enzyme, some glucose-containing scutellarein derivatives were designed and synthesized through the introduction of glucose moiety at C-7 position of scutellarein via a glucosidic bond. Biological activity evaluation showed that these glucose-containing scutellarein derivatives exhibited potent DPPH radical scavenging activities. Furthermore, the improvement of physicochemical properties such as anticoagulant and neuroprotective activities alongside with the water solubility was achieved by introducing glucose. These findings suggest that the introduction of the glucose moiety to scutellarein wattants further development of this kind of compounds as neuroprotective agents.

Synthesis and biological evaluation of 8-substituted and deglucuronidated scutellarin and baicalin analogues as antioxidant responsive element activators

Flavonoids are important bioactive dietary compounds, which are proved to be antioxidant responsive element (ARE) activators to defend against electrophilic toxicants and oxidative stress. The activators induce ARE gene transcription through Nrf2 factor, a major transcriptional stimulator of cytoprotective genes, relieved from a Keap1 complex. In this report, based on the structures of two flavonoids, scutellarin and baicalin, which are extracted from two common Chinese plants Dengzhanhua (Erigeron breviscapus (vant) Hand-Mazz) and Huangqin (Scutellaria baicalensis Georigi), respectively, we synthesized several 8-substituted and deglucuronidated analogues and identified the ARE activation effects of these flavonoids. We found that the Baicalin, deglucurnonidated Baicalin and diaza cyclopenta derivative were more active. Their dose-dependent upregulation activities of ARE and NQO1 and induction effects of Nrf2 were testified. The results presented that these three analogues had good upregulation effects on ARE, and they could be potentially utilized in relieving oxidative stress, upon further neuroprotective tests.