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4'-Hydroxyflavanone

CAS# 6515-37-3

4'-Hydroxyflavanone

Catalog No. BCN6548----Order now to get a substantial discount!

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Quality Control of 4'-Hydroxyflavanone

Number of papers citing our products

Chemical structure

4'-Hydroxyflavanone

3D structure

Chemical Properties of 4'-Hydroxyflavanone

Cas No. 6515-37-3 SDF Download SDF
PubChem ID 165506 Appearance Powder
Formula C15H12O3 M.Wt 240.26
Type of Compound Flavonoids Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name 2-(4-hydroxyphenyl)-2,3-dihydrochromen-4-one
SMILES C1C(OC2=CC=CC=C2C1=O)C3=CC=C(C=C3)O
Standard InChIKey ZLHVIYHWWQYJID-UHFFFAOYSA-N
Standard InChI InChI=1S/C15H12O3/c16-11-7-5-10(6-8-11)15-9-13(17)12-3-1-2-4-14(12)18-15/h1-8,15-16H,9H2
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Source of 4'-Hydroxyflavanone

The aerial part of Lawsonia inermis.

Biological Activity of 4'-Hydroxyflavanone

Description4'-Hydroxyflavanone may have major potential as a pharmaceutical preparation against hepatic steatosis and dyslipidemia. 4'-Hydroxyflavanone shows full vasorelaxing effects; it also shows inhibition of nitric oxide production in lipopolysaccharide (LPS)-stimulated product of nitrite in RAW 264.7 cells with the IC50 value of 15.72 ug/mL.
TargetsNO | SREBPs
In vitro

Vasorelaxing effects of flavonoids: investigation on the possible involvement of potassium channels.[Pubmed: 15378228 ]

Naunyn Schmiedebergs Arch Pharmacol. 2004 Oct;370(4):290-8.

A flavonoid-rich diet has been associated with a lower incidence of cardiovascular diseases, probably because of the antioxidant and vasoactive properties of flavonoids. Indeed, many flavonoids show vasorelaxing properties, due to different and often not yet completely clarified mechanisms of action. Among them, the activation of vascular potassium channels has been indicated as a possible pathway, accounting, at least in part, for the vasodilatory action of some flavonoid derivatives, such as apigenin and dioclein.
METHODS AND RESULTS:
Therefore, this work aims at evaluating, on in vitro isolated rat aortic rings, the endothelium-independent vasorelaxing effects of a number of flavonoid derivatives, to identify a possible activation of calcium-activated and/or ATP-sensitive potassium channels and to indicate some possible structure-activity relationships. Among the several flavonoids submitted to the pharmacological assay, only baicalein and quercetagetin were almost completely ineffective, while quercetin, hesperidin, quercitrin and rhoifolin exhibited only a partial vasorelaxing effect. On the contrary, acacetin, apigenin, chrysin, hesperetin, luteolin, pinocembrin, 4'-Hydroxyflavanone, 5-hydroxyflavone, 5-methoxyflavone, 6-hydroxyflavanone and 7-hydroxyflavone, belonging to the chemical classes of flavones and flavanones, showed full vasorelaxing effects. The vasodilatory activity of hesperetin, luteolin, 5-hydroxyflavone and 7-hydroxyflavone were antagonised by tetraethylammonium chloride, indicating the possible involvement of calcium-activated potassium channels. Moreover, iberiotoxin clearly antagonised the effects of 5-hydroxyflavone, indicating the probable importance of a structural requirement (the hydroxy group in position 5) for a possible interaction with large-conductance, calcium-activated potassium channels.
CONCLUSIONS:
Finally, glibenclamide inhibited the vasorelaxing action of luteolin and 5-hydroxyflavone, suggesting that ATP-sensitive potassium channels may also be involved in their mechanism of action.

New Diphenol and Isocoumarins from the Aerial Part of Lawsonia inermis and Their Inhibitory Activities against NO Production.[Pubmed: 27689981]

Molecules. 2016 Sep 28;21(10).

Lawsonia inermis Linn (Lythraceae), also known as henna, is a small shrub or tree distributed throughout Taiwan's Lanyu Island, in North Africa, and in Australia. Its leaves are used as a folk medicine for the treatment of external hemorrhage and fingernail abscesses.
METHODS AND RESULTS:
Investigation of the ethyl acetate (EtOAc)-soluble fractions from methanol extract of the aerial part of Lawsonia inermis has led to the isolation of a new diphenol, (Z)-4,4'-(prop-1-ene-1,3-diyl)diphenol (1), two new isocoumarin carbonates, inermiscarbonates A (2) and B (3), and six known compounds, 4'-Hydroxyflavanone (4), apigenine (5), kampferol (6), luteolin (7), quercetin (8), and (-)-catechin (9). Their structures were determined by detailed analysis of spectroscopic data and comparison with the data of known analogues.
CONCLUSIONS:
Compounds 1 and 4-9 were evaluated for the inhibition of nitric oxide production in lipopolysaccharide (LPS)-stimulated product of nitrite in RAW 264.7 cells with IC50 values of 5.63, 15.72, 8.67, 6.67, 6.17, 7.61, and 14.52 μg/mL, respectively.

Protocol of 4'-Hydroxyflavanone

Kinase Assay

4'-Hydroxyflavanone suppresses activation of sterol regulatory element-binding proteins and de novo lipid synthesis.[Pubmed: 22634867 ]

FEBS Lett. 2012 Jun 21;586(13):1778-82.

Sterol regulatory element-binding proteins (SREBPs) are major transcription factors that regulate the expression of genes involved in fatty acid and cholesterol biosynthesis.
METHODS AND RESULTS:
Here we show that 4'-Hydroxyflavanone (4'-HF) impairs the fatty acid synthase promoter activity and reduces the activation of SREBPs and their target gene expression in human hepatoma Huh-7 cells. Moreover, 4'-HF suppresses de novo fatty acid and cholesterol synthesis.
CONCLUSIONS:
This study identifies 4'-HF as an inhibitor of SREBP maturation and lipid synthesis, and provides evidence that 4'-HF may have major potential as a pharmaceutical preparation against hepatic steatosis and dyslipidemia.

4'-Hydroxyflavanone Dilution Calculator

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4'-Hydroxyflavanone Molarity Calculator

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Preparing Stock Solutions of 4'-Hydroxyflavanone

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 4.1622 mL 20.8108 mL 41.6216 mL 83.2432 mL 104.0539 mL
5 mM 0.8324 mL 4.1622 mL 8.3243 mL 16.6486 mL 20.8108 mL
10 mM 0.4162 mL 2.0811 mL 4.1622 mL 8.3243 mL 10.4054 mL
50 mM 0.0832 mL 0.4162 mL 0.8324 mL 1.6649 mL 2.0811 mL
100 mM 0.0416 mL 0.2081 mL 0.4162 mL 0.8324 mL 1.0405 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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References on 4'-Hydroxyflavanone

4'-Hydroxyflavanone suppresses activation of sterol regulatory element-binding proteins and de novo lipid synthesis.[Pubmed:22634867]

FEBS Lett. 2012 Jun 21;586(13):1778-82.

Sterol regulatory element-binding proteins (SREBPs) are major transcription factors that regulate the expression of genes involved in fatty acid and cholesterol biosynthesis. Here we show that 4'-hydroxyflavanone (4'-HF) impairs the fatty acid synthase promoter activity and reduces the activation of SREBPs and their target gene expression in human hepatoma Huh-7 cells. Moreover, 4'-HF suppresses de novo fatty acid and cholesterol synthesis. This study identifies 4'-HF as an inhibitor of SREBP maturation and lipid synthesis, and provides evidence that 4'-HF may have major potential as a pharmaceutical preparation against hepatic steatosis and dyslipidemia.

New Diphenol and Isocoumarins from the Aerial Part of Lawsonia inermis and Their Inhibitory Activities against NO Production.[Pubmed:27689981]

Molecules. 2016 Sep 28;21(10). pii: molecules21101299.

Lawsonia inermis Linn (Lythraceae), also known as henna, is a small shrub or tree distributed throughout Taiwan's Lanyu Island, in North Africa, and in Australia. Its leaves are used as a folk medicine for the treatment of external hemorrhage and fingernail abscesses. Investigation of the ethyl acetate (EtOAc)-soluble fractions from methanol extract of the aerial part of Lawsonia inermis has led to the isolation of a new diphenol, (Z)-4,4'-(prop-1-ene-1,3-diyl)diphenol (1), two new isocoumarin carbonates, inermiscarbonates A (2) and B (3), and six known compounds, 4'-hydroxyflavanone (4), apigenine (5), kampferol (6), luteolin (7), quercetin (8), and (-)-catechin (9). Their structures were determined by detailed analysis of spectroscopic data and comparison with the data of known analogues. Compounds 1 and 4-9 were evaluated for the inhibition of nitric oxide production in lipopolysaccharide (LPS)-stimulated product of nitrite in RAW 264.7 cells with IC50 values of 5.63, 15.72, 8.67, 6.67, 6.17, 7.61, and 14.52 mug/mL, respectively.

Vasorelaxing effects of flavonoids: investigation on the possible involvement of potassium channels.[Pubmed:15378228]

Naunyn Schmiedebergs Arch Pharmacol. 2004 Oct;370(4):290-8.

A flavonoid-rich diet has been associated with a lower incidence of cardiovascular diseases, probably because of the antioxidant and vasoactive properties of flavonoids. Indeed, many flavonoids show vasorelaxing properties, due to different and often not yet completely clarified mechanisms of action. Among them, the activation of vascular potassium channels has been indicated as a possible pathway, accounting, at least in part, for the vasodilatory action of some flavonoid derivatives, such as apigenin and dioclein. Therefore, this work aims at evaluating, on in vitro isolated rat aortic rings, the endothelium-independent vasorelaxing effects of a number of flavonoid derivatives, to identify a possible activation of calcium-activated and/or ATP-sensitive potassium channels and to indicate some possible structure-activity relationships. Among the several flavonoids submitted to the pharmacological assay, only baicalein and quercetagetin were almost completely ineffective, while quercetin, hesperidin, quercitrin and rhoifolin exhibited only a partial vasorelaxing effect. On the contrary, acacetin, apigenin, chrysin, hesperetin, luteolin, pinocembrin, 4'-hydroxyflavanone, 5-hydroxyflavone, 5-methoxyflavone, 6-hydroxyflavanone and 7-hydroxyflavone, belonging to the chemical classes of flavones and flavanones, showed full vasorelaxing effects. The vasodilatory activity of hesperetin, luteolin, 5-hydroxyflavone and 7-hydroxyflavone were antagonised by tetraethylammonium chloride, indicating the possible involvement of calcium-activated potassium channels. Moreover, iberiotoxin clearly antagonised the effects of 5-hydroxyflavone, indicating the probable importance of a structural requirement (the hydroxy group in position 5) for a possible interaction with large-conductance, calcium-activated potassium channels. Finally, glibenclamide inhibited the vasorelaxing action of luteolin and 5-hydroxyflavone, suggesting that ATP-sensitive potassium channels may also be involved in their mechanism of action.

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