6665-86-7

Basic information

• Product Name: 7-HYDROXYFLAVONE
• Synonyms: TIMTEC-BB SBB005921;7-HYDROXYFLAVONE;7-HYDROXY-2-PHENYL-4H-CHROMEN-4-ONE;7-HYDROXY-2-PHENYLCHROMONE;HYDROXYFLAVONE, 7-;7-hydroxy-2-phenyl-4-benzopyrone;7-Hydroxyflavone,98%;HYDROXYFLAVONE, 7-(RG)
• CAS NO: 6665-86-7
• Molecular Formula: C₁₅H₁₀O₃
• Molecular Weight: 238.24
• EINECS: 229-705-3
• Product Categories: Mono-substituted Flavones;Biochemistry;Flavonoids
• Mol File: 6665-86-7.mol
• Article Data: 61

Chemical Properties

• Melting Point: 245-247 °C(lit.)
• Boiling Point: 320.83°C (rough estimate)
• Flash Point: 176.3 °C
• Appearance: off-white crystals
• Density: 1.340±0.06 g/cm3 (20 ºC 760 Torr)
• Vapor Pressure: 1.02E-08mmHg at 25°C
• Refractive Index: 1.5740 (estimate)
• PKA: 7.02±0.40(Predicted)
• Water Solubility: Insoluble in water
• BRN: 194089
• CAS DataBase Reference: 7-HYDROXYFLAVONE(CAS DataBase Reference)
• NIST Chemistry Reference: 7-HYDROXYFLAVONE(6665-86-7)
• EPA Substance Registry System: 7-HYDROXYFLAVONE(6665-86-7)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 3
• Hazardous Substances Data: 6665-86-7(Hazardous Substances Data)

Usage

Description

7-Hydroxyflavone is a naturally occurring flavonoid compound characterized by the presence of a hydroxyl group at the 7th position of its molecular structure. It is known for its diverse range of biological activities and potential applications in various fields.

Uses

Used in Pharmaceutical Industry:
7-Hydroxyflavone is used as an antifungal agent for its ability to inhibit the growth of various fungi, making it a valuable component in the development of antifungal medications.
7-Hydroxyflavone is also used as an analgesic, providing pain relief and managing discomfort in various conditions.
Used in Organic Synthesis:
7-Hydroxyflavone serves as a biologically valuable acceptor in O-glycosidation reactions, which are crucial for the synthesis of various biologically active compounds.
It is involved in the synthesis of fully phosphorylated flavones, which are used as pancreatic cholesterol esterase inhibitors, playing a role in managing cholesterol levels.
7-Hydroxyflavone is used for O-methylation with di-Me carbonate, a process that modifies its structure and enhances its biological properties.
It is linked by a polymethylene chain for the synthesis of α1-adrenoceptor antagonists, which are used in the treatment of various cardiovascular and urological conditions.
7-Hydroxyflavone is involved in Baylis-Hillman reactions, which are significant in the synthesis of complex organic molecules with potential pharmaceutical applications.
It is also involved in phase-transfer catalyzed glucosylation for the synthesis of glucosylated flavonoids, which have potential applications in the development of new drugs and therapeutic agents.

Synthesis

Acetylation of resorcinol acetic acid yields 2,4-dihydroxyacetophenone, which is then subjected to benzoylation and transposition to obtain (2-hydroxy-4-benzoyloxy)benzoylacetophenone. 7-hydroxyflavone was obtained by further cyclization reaction in a mixture of acetic acid and hydrochloric acid at 103° C for 7 h.

Biological Activity

7-Hydroxyflavone is a flavonoid isolated from M. indica with anti-inflammatory properties. It protects renal cells from nicotine (NIC)-induced cytotoxicity through the ERK/Nrf2/HO-1 pathway.

InChI:InChI=1/C15H10O3/c16-11-6-7-12-13(17)9-14(18-15(12)8-11)10-4-2-1-3-5-10/h1-9,16H

Upstream product

• 95161-88-9 7-(benzyloxy)-2-phenyl-4H-chromen-4-one 
• 117096-61-4 7-hydroxy-2-phenyl-3-benzoylchromone 
• 952018-33-6 1-(2-hydroxy-4-tetrahydropyran-2-yloxy-phenyl)-3-phenyl-propane-1,3-dione 
• 5465-06-5 <4-(benzoyloxy)-2-hydroxybenzoyl>benzoylmethane 
• 127-09-3 sodium acetate 
• 64-19-7 acetic acid 
• 130483-43-1 1-<2-hydroxy-4-(methoxymethoxy)phenyl>-3-phenylpropane-1,3-dione 
• 552-41-0 1-(2-hydroxy-4-methoxyphenyl)ethanone 
• 98-88-4 benzoyl chloride 
• 673-22-3 2-Hydroxy-4-methoxybenzaldehyde 
• 4891-38-7 phenylpropynoic acid methyl ester 
• 25015-92-3 2-chloro-1-(2,4-dihydroxyphenyl)ethanone 
• 100-52-7 benzaldehyde 
• 5706-85-4 2-hydroxy-1-(4-hydroxyphenyl)ethan-1-one 

Downstream Products

• 102080-28-4 diethyl flavon-7-yl phosphate 
• 39103-37-2 7-benzoyloxy-2-phenyl-4H-1-benzopyran-4-one 
• 140439-26-5 7-[4-(4-hydroxypiperidinyl)butoxy]-2-phenyl-4H-1-benzopyran-4-one hydrochloride 
• 140439-06-1 7-[5-(4-hydroxypiperidinyl)pentoxy]-2-phenyl-4H-1-benzopyran-4-one 
• 119161-55-6 7-(4-Pentenoxy)flavone 

Relevant articles and documents

Design, synthesis and apoptosis inducing activity of nonsteroidal flavone-methanesulfonate derivatives on MCF-7 cell line as potential sulfatase inhibitor

In recent years, focusing on new potent anticancer agents with selective activity is one of the greatest challenges in cancer therapy. Breast cancer is the most common cancer and the main cause of cancer deaths in women. The sulfatase enzyme plays an important role in converting the sulfated steroids into non-sulfate steroid hormones, which increases the growth and development of many hormone-dependent cancers, such as breast cancer. In this regard, structure-based optimization was conducted to design novel flavone-sulfonates pharmacophore as a new steroid sulfatase inhibitor. In the present work, the conventional methods for the synthesis of 4-oxo-2-phenyl-4H-chromen-7-yl methanesulfonate derivatives were reported. Their cytotoxicity was evaluated with MTT assay against a breast cancer cell line (MCF-7). The apoptosis inducing activity of the most cytotoxic compound 3c with an IC50 value of 0.615 μM was evaluated in comparison to docetaxel in the presence of estradiol which is a crucial growth factor to survive the cancerous cells. The results of double staining Annexin V-FITC/PI analysis suggested that the cytotoxic activity of this compound 3c in MCF-7 cells occurs via apoptosis. Molecular docking studies were conducted to clarify the inhibition mode of the most promising compound (3c) over the sulfatase (1P49) binding site. The analysis revealed the role of hydrogen bond interaction with Gly181 and hydrophobic interactions through the 1P49 active site in the ligand-receptor complex as significant descriptors to rationalize the potential inhibition activity. [Figure not available: see fulltext.]

Divergent synthesis of flavones and flavanones from 2′-hydroxydihydrochalconesviapalladium(ii)-catalyzed oxidative cyclization

Divergent and versatile synthetic routes to flavones and flavanonesviaefficient Pd(ii) catalysis are disclosed. These Pd(ii) catalyses expediently provide a variety of flavones and flavanones from 2′-hydroxydihydrochalcones as common intermediates, depending on oxidants and additives,viadiscriminate oxidative cyclization sequences involving dehydrogenation, respectively, in a highly atom-economic manner.

Flavonoid analogues as urease inhibitors: Synthesis, biological evaluation, molecular docking studies and in-silico ADME evaluation

A series of novel flavonoid analogues were designed and synthesized. The aimed compounds for urease inhibitory activities were clearly superior to the control drug thiourea (more than 10 times). Among these compounds, L2 (IC50 = 1.343 μM) and L12 (IC50 = 1.207 μM) exhibited the most excellent urease inhibitory activity in vitro. The molecular dockings of L2, L12 and L22 into urease were performed to explore the binding modes and their structure-activity relationship. Furthermore, these aimed compounds showed good druggable properties.