2196-14-7

Usage

Uses

Used in Pharmaceutical Industry:
7,4'-DIHYDROXYFLAVONE is used as a bioactive agent for its potential therapeutic applications. It is involved in methods that convert from anions to molecules, which may contribute to its pharmacological properties and effectiveness in treating various health conditions.
Used in Nutraceutical Industry:
7,4'-DIHYDROXYFLAVONE can be utilized as a nutraceutical ingredient due to its natural occurrence in plants and potential health benefits. Its presence in dietary supplements and functional foods may contribute to promoting overall well-being and supporting specific health-related functions.
Used in Cosmetic Industry:
In the cosmetic industry, 7,4'-DIHYDROXYFLAVONE may be employed for its antioxidant and anti-inflammatory properties. It can be incorporated into skincare products to protect the skin from oxidative stress and inflammation, potentially improving skin health and appearance.
Used in Agricultural Industry:
7,4'-DIHYDROXYFLAVONE may also find applications in the agricultural sector, particularly in the development of plant protection products. Its bioactive properties could be harnessed to enhance crop resistance against pests and diseases, contributing to sustainable agriculture practices.

InChI:InChI=1/C15H10O4/c16-10-3-1-9(2-4-10)14-8-13(18)12-6-5-11(17)7-15(12)19-14/h1-8,16-17H

Upstream product

• 132018-31-6 4'-amino-7-hydroxyflavone 
• 101279-24-7 4,7-dihydroxy-3-(4-hydroxy-benzoyl)-coumarin 
• 961-29-5 isoliquirtigenin 
• 20979-50-4 4,7-dimethoxyflavone 
• 67-56-1 methanol 
• 6665-86-7 7-hydroxyflavone 
• 41046-68-8 4-iodobenzene-1,3-diol 
• 89-84-9 2',4'-dihydroxy-4-acetophenone 
• 131944-42-8 7-hydroxy-2-(4'-nitrophenyl)chromone 
• 578-86-9 liquiritigenin 
• 25015-92-3 2-chloro-1-(2,4-dihydroxyphenyl)ethanone 
• 123-08-0 4-hydroxy-benzaldehyde 
• 108-46-3 recorcinol 
• 755722-84-0 imine 

Downstream Products

• 109688-07-5 7-acetoxy-2-(4-acetoxy-phenyl)-chromen-4-one 
• 32272-23-4 2-(4-hydroxyphenyl)-7-methoxychromen-4-one 
• 20979-50-4 4,7-dimethoxyflavone 
• 22052-75-1 kumatakenin B-4'-O-glucoside 
• 578-74-5 apigenin 7-O-glucoside 
• 28757-27-9 Apigenin 5-O-β-D-glucopyranoside 
• 69097-97-8 7,4'-dihydroxy-dihydroflavone 
• 3681-96-7 kumatakenin B 8-C-β-D-glucoside 

Relevant academic research and scientific papers

Flavone synthase II (CYP93B16) from soybean (Glycine max L.)

Flavonoids are a very diverse group of plant secondary metabolites with a wide array of activities in plants, as well as in nutrition and health. All flavonoids are derived from a limited number of flavanone intermediates, which serve as substrates for a variety of enzyme activities, enabling the generation of diversity in flavonoid structures. Flavonoids can be characteristic metabolites, like isoflavonoids for legumes. Others, like flavones, occur in nearly all plants. Interestingly, there exist two fundamentally different enzymatic systems able to directly generate flavones from flavanones, flavone synthase (FNS) I and II. We describe an inducible flavone synthase activity from soybean (Glycine max) cell cultures, generating 7,4′-dihydroxyflavone (DHF), which we classified as FNS II. The corresponding full-length cDNA (CYP93B16) was isolated using known FNS II sequences from other plants. Functional expression in yeast allowed the detailed biochemical characterization of the catalytic activity of FNS II. A direct conversion of flavanones such as liquiritigenin, naringenin, and eriodictyol into the corresponding flavones DHF, apigenin and luteolin, respectively, was demonstrated. The enzymatic reaction of FNS II was stereoselective, favouring the (S)- over the (R)-enantiomer. Phylogenetic analyses of the subfamily of plant CYP93B enzymes indicate the evolution of a gene encoding a flavone synthase which originally catalyzed the direct conversion of flavanones into flavones, via early gene duplication into a less efficient enzyme with an altered catalytic mechanism. Ultimately, this allowed the evolution of the legume-specific isoflavonoid synthase activity.

Synthesis and studies of flavone and bis-flavone derivatives

Flavonoids are widely occurring polyphenols of plant origin and well explored in the field of pharmacological activities. Recent studies showed this scaffold to be more dynamic as fluorescent probe. Very rare reports are there in literature on flavones as liquid crystals, for the first time we have synthesized and characterized flavone and bis-flavone derivatives for mesomorphic properties. Compounds 9a–d and 13a–d were studied for liquid crystalline properties by Differential scanning calorimetry (DSC) and Polarizing optical microscopy (POM) studies. The compounds 8, 9a–d, 12, and 13a–d were also studied for antioxidant property by DPPH assay.

Isoliquiritigenin Derivatives Inhibit RANKL-Induced Osteoclastogenesis by Regulating p38 and NF-κB Activation in RAW 264.7 Cells

Bone diseases may not be imminently life-threatening or a leading cause of death such as heart diseases or cancers. However, as aging population grows in almost every part of the world, they surely impose significant socioeconomic burden on the society, not to mention the patients and their families. Osteoporosis is the most common type of bone disease, which frequently develops in seniors, especially in postmenopausal women. Although currently several anti-osteoclastic drugs designed to suppress excessive osteoclast activation, a major cause of osteoporosis, are commercially available, accompanying adverse effects ranging from mild to severe have been reported as well. Natural products have become increasingly popular because of their effectiveness with fewer side effects. Isoliquiritigenin (ILG), a natural flavonoid from licorice, has been reported to suppress osteoclast differentiation and activation. In the present study, newly synthesized ILG derivatives were screened for their anti-osteoporotic activity as more potent substitute candidates to ILG. Out of the 12 ILG derivatives tested, two compounds demonstrated significantly improved bone loss in vitro by inhibiting both osteoclastogenesis and osteoclast activity. The results of the present study indicate that these compounds may serve as a potential drug for osteoporosis and warrant further studies to evaluate their in vivo efficacy.

A method of synthesizing the glycyrrhizin (by machine translation)

The invention relates to a synthetic chemical method of glycyrrhizin. In order to 2, 4 - dihydroxy acetophenone and 4 - hydroxy benzoic acid ethyl ester as the raw material, the protective group for a hydroxyl, keto ester condensation, cyclization and hyd

Identification of metabolites of liquiritin in rats by UHPLC-Q-TOF-MS/MS: Metabolic profiling and pathway comparison: In vitro and in vivo

Liquiritin (LQ), the main bioactive constituent of licorice, is a common flavoring and sweetening agent in food products and has a wide range of pharmacological properties, including antidepressant-like, neuroprotective, anti-cancer and anti-inflammatory properties. This study investigated the metabolic pathways of LQ in vitro (rat liver microsomes) and in vivo (rat model) using ultra high-performance liquid chromatography coupled with hybrid triple quadrupole time-of-flight mass spectrometry (UHPLC-Q-TOF-MS/MS). Moreover, supplementary tools such as key product ions (KPIs) were employed to search for and identify compounds. As a result, 56 in vivo metabolites and 15 in vitro metabolites were structurally characterized. Oxidation, reduction, hydrolysis, methylation, acetylation, and sulfate and glucuronide conjugation were determined to be the major metabolic pathways of LQ, and there were differences in LQ metabolism in vitro and in vivo. In addition, the in vitro and in vivo metabolic pathways were compared in this study.

Synthesis and antiproliferative activity of some dihydro-1 H-furo[2,3-c]pyrazole-Flavone hybrids

A new series of dihydro-1 H-furo[2,3-c]pyrazole-flavone hybrids were synthesized from one-pot four-component reaction of β-keto ester (1), hydrazine (2),7-hydroxy 8-formyl flavones (3), pyridiniumylide (4) in presence of NEt3 as catalyst under ethanol reflux conditions and their antiproliferative properties were evaluated against human cancer cell lines, namely, laryngeal carcinoma (Hep2), lung adenocarcinoma (A549) and cervical cancer (HeLa). The best among them, furo[2,3-c]pyrazole-flavone with C4′-methoxy substitution was selected for further structure activity relationship (SAR) studies. Among the derivatives, (4S,5S)-ethyl 4-(7-hydroxy-5-methoxy-4-oxo-2-(2,4,6-trimethoxyphenyl)-4H-chromen-8-yl)-3-methyl-4,5-dihydro-1 H-furo[2,3-c]pyrazole-5-carboxylate (8r) showed most potent cytotoxic activity against all three cancer cell lines. Toxicity studies revealed that the dihydro-1H-furo[2,3-c]pyrazole-flavones are specifically target the cancer cell lines.

Synthesis of a series of novel dihydroartemisinin monomers and dimers containing chalcone as a linker and their anticancer activity

A new series of monomer and dimer derivatives of dihydroartemisinin (DHA) containing substituted chalcones as a linker were synthesized and investigated for their cytotoxicity in human cancer cell lines HL-60 (leukemia), Mia PaCa-2 (pancreatic cancer), PC

Inhibitory effect of flavonoids on human glutaminyl cyclase

Glutaminyl cyclase (QC) plays an important role in the pathogenesis of Alzheimer's disease (AD) and can be a potential target for the development of novel anti-AD agents. However, the study of QC inhibitors are still less. Here, phenol-4′ (R1-), C5-OH (R2-) and C7-OH (R3-) modified apigenin derivatives were synthesized as a new class of human QC (hQC) inhibitors. The efficacy investigation of these compounds was performed by spectrophotometric assessment and the structure-activity relationship (SAR) was evaluated. Molecular docking was also carried out to analyze the binding mode of the synthesized flavonoid to the active site of hQC.

Design, synthesis and evaluation of novel 7-aminoalkyl-substituted flavonoid derivatives with improved cholinesterase inhibitory activities

A novel series of 7-aminoalkyl-substituted flavonoid derivatives 5a-5r were designed, synthesized and evaluated as potential cholinesterase inhibitors. The results showed that most of the synthesized compounds exhibited potent acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) inhibitory activities at the micromolar range. Compound 2-(naphthalen-1-yl)-7-(8-(pyrrolidin-1-yl)octyloxy)-4H-chromen-4-one (5q) showed the best inhibitory activity (IC50, 0.64 μM for AChE and 0.42 μM for BChE) which were better than our previously reported compounds and the commercially available cholinergic agent Rivastigmine. The results from a Lineweaver-Burk plot indicated a mixed-type inhibition for compound 5q with AChE and BChE. Furthermore, molecular modeling study showed that 5q targeted both the catalytic active site (CAS) and the peripheral anionic site (PAS) of AChE. Besides, these compounds (5a-5r) did not affect PC12 and HepG2 cell viability at the concentration of 10 μM. Consequently, these flavonoid derivatives should be further investigated as multipotent agents for the treatment of Alzheimer's disease.

COMPOUNDS FOR IMMUNOPOTENTIATION

Methods of stimulating an immune response and treating patients responsive thereto with 3,4-di(1H-indol-3-yl)-1H-pyrrole-2,5-diones, staurosporine analogs, derivatized pyridazines, chromen-4-ones, indolinones, quinazolines, nucleoside analogs, and other small molecules are disclosed.