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7-Hydroxyflavone
7-Hydroxyflavone
ChemFaces products have been cited in many studies from excellent and top scientific journals
Product Name 7-Hydroxyflavone
Price: $30 / 20mg
CAS No.: 6665-86-7
Catalog No.: CFN92768
Molecular Formula: C15H10O3
Molecular Weight: 238.2 g/mol
Purity: >=98%
Type of Compound: Flavonoids
Physical Desc.: Powder
Source: The barks of Acacia farnesiana.
Solvent: Chloroform, Dichloromethane, Ethyl Acetate, DMSO, Acetone, etc.
Download: COA    MSDS    SDF
Similar structural: Comparison (Web)  (SDF)
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According to end customer requirements, ChemFaces provide solvent format. This solvent format of product intended use: Signaling Inhibitors, Biological activities or Pharmacological activities.
Size /Price /Stock 10 mM * 1 mL in DMSO / $8.9 / In-stock
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Related Screening Libraries
Size /Price /Stock 10 mM * 100 uL in DMSO / Inquiry / In-stock
10 mM * 1 mL in DMSO / Inquiry / In-stock
Related Libraries
Biological Activity
Description: 7-Hydroxyflavone is a potent inhibitor of CYP1A1 with a Ki value of 0.015 μM and exhibits 6-fold greater selectivity for CYP1A1 over CYP1A2. It also has excellent antioxidant, anti-inflammatory, and anti-proliferation properties, it may serve as potential protective agents in the treatment of patients with chronic EV71 infection.7-Hydroxyflavone can protect renal cells from NIC-associated cytotoxicity via the ERK/Nrf2/HO-1 pathway; it also can inhibit LPS-induced inflammation via attenuating the production of NO, PGE2 , TNF-α and IL-6.
Targets: ERK | Nrf2 | HO-1 | cAMP | p21 | PARP | PDE | Calcium Channel | NO | PGE | COX | TNF-α | NOS | IL Receptor | PKA | CYP1A1 | CYP1A2
In vitro:
PLoS One. 2014 Mar 24;9(3):e92565.
Inhibition of Enterovirus 71 replication by 7-hydroxyflavone and diisopropyl-flavon7-yl Phosphate.[Pubmed: 24664133]
Enterovirus 71 (EV71) is the major causative agent of hand, foot, and mouth disease, which has been continuously prevalent in Asia in recent years. In children, severe cases can lead to death, and no prophylactic or therapeutic measures against EV71 infection are available. The 3C proteases of EV71 play an important role in viral replication and are an ideal drug target. In previous work, we resolved the crystal structure for EV71 3Cpro.
METHODS AND RESULTS:
In this report, we took advantage of the automated docking program AutoDock 4.0 to simulate EV71 3Cpro-ligand conformation. 7-Hydroxyflavone (HF) and its phosphate ester(FIP) were predicted to bind with EV71 3Cpro.In an in vitro protease inhibition assay, FIP inhibited EV71 3Cpro protease activity. Both flavones were highly active against EV71, protecting cells from EV71 infection. Replication of viral RNA and formation of EV71 plaque were all strongly inhibited in cells.
CONCLUSIONS:
These results indicated that HF and FIP may serve as potential protective agents in the treatment of patients with chronic EV71 infection.
PLoS One. 2012;7(5):e36652.
Inhibitory effects and underlying mechanism of 7-hydroxyflavone phosphate ester in HeLa cells.[Pubmed: 22574207]
Chrysin and its phosphate ester have previously been shown to inhibit cell proliferation and induce apoptosis in Hela cells; however, the underlying mechanism remains to be characterized.
METHODS AND RESULTS:
In the present study, we therefore synthesized diethyl flavon-7-yl phosphate (FP, C(19)H(19)O(6)P) by a simplified Atheron-Todd reaction, and explored its anti-tumor characteristics and mechanisms. Cell proliferation, cell cycle progression and apoptosis were measured by MTS, flow cytometry and terminal deoxynucleotidyl transferase dUTP nick end labeling techniques, respectively in human cervical cancer HeLa cells treated with 7-Hydroxyflavone (HF) and FP. p21, proliferating cell nuclear antigen (PCNA) and cAMP levels in Hela cells were analyzed by western blot and radioimmunoassay. Both HF and FP inhibited proliferation and induced apoptosis in HeLa cells via induction of PCNA/p21 expression, cleaved caspase-3/poly (ADP-ribose) polymerase (PARP)-1, elevation of cAMP levels, and cell cycle arrest with accumulation of cells in the G0/G1 fraction. The effects of FP were more potent than those of HF. The interactions of FP with Ca(2+)-calmodulin (CaM) and Ca(2+)-CaM-phosphodiesterase (PDE)1 were explored by electrospray ionization-mass spectrometry and fluorescence spectra. FP, but not HF, formed non-covalent complexes with Ca(2+)-CaM-PDE1, indicating that FP is an inhibitor of PDE1, and resulting in elevated cellular cAMP levels. It is possible that the elevated cAMP levels inhibit growth and induce apoptosis in Hela cells through induction of p21 and cleaved caspase-3/PARP-1 expression, and causing down-regulation of PCNA and cell cycle arrest with accumulation of cells in the G0/G1 and G2/M fractions. In conclusion, FP was shown to be a Ca(2+)-CaM-PDE inhibitor, which might account for its underlying anti-cancer mechanism in HeLa cells.
CONCLUSIONS:
These observations clearly demonstrate the special roles of phosphorylated flavonoids in biological processes, and suggest that FP might represent a potential new drug for the therapy of human cervical carcinoma.
7-Hydroxyflavone Description
Source: The barks of Acacia farnesiana.
Solvent: Chloroform, Dichloromethane, Ethyl Acetate, DMSO, Acetone, etc.
Storage: Providing storage is as stated on the product vial and the vial is kept tightly sealed, the product can be stored for up to 24 months(2-8C).

Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20C. Generally, these will be useable for up to two weeks. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour.

Need more advice on solubility, usage and handling? Please email to: service@chemfaces.com

After receiving: The packaging of the product may have turned upside down during transportation, resulting in the natural compounds adhering to the neck or cap of the vial. take the vial out of its packaging and gently shake to let the compounds fall to the bottom of the vial. for liquid products, centrifuge at 200-500 RPM to gather the liquid at the bottom of the vial. try to avoid loss or contamination during handling.
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Recently, ChemFaces products have been cited in many studies from excellent and top scientific journals

Cell. 2018 Jan 11;172(1-2):249-261.e12.
doi: 10.1016/j.cell.2017.12.019.
IF=36.216(2019)

PMID: 29328914

Cell Metab. 2020 Mar 3;31(3):534-548.e5.
doi: 10.1016/j.cmet.2020.01.002.
IF=22.415(2019)

PMID: 32004475

Mol Cell. 2017 Nov 16;68(4):673-685.e6.
doi: 10.1016/j.molcel.2017.10.022.
IF=14.548(2019)

PMID: 29149595

ACS Nano. 2018 Apr 24;12(4): 3385-3396.
doi: 10.1021/acsnano.7b08969.
IF=13.903(2019)

PMID: 29553709

Nature Plants. 2016 Dec 22;3: 16206.
doi: 10.1038/nplants.2016.205.
IF=13.297(2019)

PMID: 28005066

Sci Adv. 2018 Oct 24;4(10): eaat6994.
doi: 10.1126/sciadv.aat6994.
IF=12.804(2019)

PMID: 30417089
Calculate Dilution Ratios(Only for Reference)
1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 4.1982 mL 20.9908 mL 41.9815 mL 83.9631 mL 104.9538 mL
5 mM 0.8396 mL 4.1982 mL 8.3963 mL 16.7926 mL 20.9908 mL
10 mM 0.4198 mL 2.0991 mL 4.1982 mL 8.3963 mL 10.4954 mL
50 mM 0.084 mL 0.4198 mL 0.8396 mL 1.6793 mL 2.0991 mL
100 mM 0.042 mL 0.2099 mL 0.4198 mL 0.8396 mL 1.0495 mL
* Note: If you are in the process of experiment, it's need to make the dilution ratios of the samples. The dilution data of the sheet for your reference. Normally, it's can get a better solubility within lower of Concentrations.
Protocol
Kinase Assay:
PLoS One. 2017 Jun 22;12(6):e0179777.
Differential roles of 3-Hydroxyflavone and 7-Hydroxyflavone against nicotine-induced oxidative stress in rat renal proximal tubule cells.[Pubmed: 28640852 ]
Plant flavonoids are well known as antioxidants against oxidative stress induced by exposure to external pollutants. Nicotine (NIC) is one of those agents which increases renal oxidative stress, an important factor in the pathogenesis of renal epithelial injury in smokers. Although several studies had been conducted on flavonoids and oxidative stress, the mechanism of the protective pathways are not fully understood.
METHODS AND RESULTS:
Here, we present studies on antioxidant properties of two mono-hydroxyflavone isomers, 3-hydroxyflanove (3HF)- and 7-Hydroxyflavone (7HF), against nicotine-associated oxidative stress and injury in cultured renal proximal tubule cells and correlate their antioxidant properties with their chemical structure. Our data clearly demonstrates, for the first time, that while both 3HF and 7HF protect renal cells from NIC-associated cytotoxicity, the mechanism of their action is different: 3HF elicits protective activity via the PKA/CREB/MnSOD pathway while 7HF does so via the ERK/Nrf2/HO-1 pathway. Molecular docking and dynamics simulations with two major signaling pathway proteins showed significant differences in the binding energies of 3HF (-5.67 and -7.39 kcal.mol-1) compared to 7HF (-5.41 and -8.55 kcal.mol-1) in the matrices of CREB and Keap1-Nrf2 proteins respectively, which corroborate with the observed differences in their protective properties in the renal cells.
CONCLUSIONS:
The implications of this novel explorative study is likely to promote the understanding of the mechanisms of the antioxidative functions of different flavones.
Cell Research:
J Pharm Pharmacol. 2017 Jul;69(7):865-874.
Inhibition of pro-inflammatory mediators in RAW264.7 cells by 7-hydroxyflavone and 7,8-dihydroxyflavone.[Pubmed: 28295316 ]
Flavonoids are a class of compounds that having the benzo-γ-pyrone skeleton, which possess anti-inflammatory properties in vitro and in vivo. The aim of this study was to investigate the inhibition of two flavonoids 7-Hydroxyflavone (HF) and 7,8-dihydroxyflavone (DHF) on the production of pro-inflammatory mediators in RAW264.7 cells activated by lipopolysaccharides (LPS).
METHODS AND RESULTS:
For this purpose, we selected four pro-inflammatory mediators including nitric oxide (NO), prostaglandin E2 (PGE2 ), tumour necrosis factor-α (TNF-α) and interleukin-6 (IL-6) as markers to evaluate the anti-inflammatory activity of HF and DHF. In this regard, we showed that HF and DHF dose-dependently reduced the production of NO, PGE2 , TNF-α and IL-6 through downregulating mRNA expression of inducible nitric oxide synthase (iNOS), cyclooxygenase 2 (COX2), TNF-α and IL-6, respectively. Moreover, DHF generally possesses more efficient than HF in reducing these markers secretion in this study.
CONCLUSIONS:
Consider together, these findings suggest that DHF and HF can inhibit LPS-induced inflammation via attenuating the production of NO, PGE2 , TNF-α and IL-6, indicating that they may be lead compounds for developing anti-inflammatory agent.
Structure Identification:
J Phys Chem A. 2014 May 1;118(17):3068-80.
7-hydroxyflavone revisited: spectral, acid-base properties, and interplay of the protolytic forms in the ground and excited states.[Pubmed: 24689737]
Spectral and acid-base properties of 7-Hydroxyflavone (7HF) in the ground and excited states were investigated with a purpose to enable reasonable application of this dye and its derivatives as fluorescent probes.
METHODS AND RESULTS:
Analysis of solvatochromic and solvatofluorochromic ability of 7HF in 20 solvents, investigations of 7HF spectral properties in the frozen solvents, spectrophotometric and spectrofluorimetric titrations in methanol-water (4:1 v/v) in the wide pH/H0 range (from pH = 11.0 to H0 = -4.5), analysis of the 3D fluorescence and time-resolved spectra, as well as quantum-chemical calculations were carried out. It has been found that 7HF can exist in three protolythic forms-neutral, anion, and cation-depending on the environment acidity or basicity. In the excited state, in methanol-water solutions, there are four forms: neutral, cation and anion, which can be formed by direct excitation of the ground-state anion or by photodissociation of the neutral form depending on pH, and only one phototautomer, which appears in the H0 range from 1.3 to -4.5.
CONCLUSIONS:
It has been shown that the mechanism of the phototautomer formation depends on medium acidity. The photoautomer can be formed by cation photodissociation as well as by photoanion protonation. Finally, it was concluded which of the 7HF protolytic forms can be used for fluorescent probing.
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