3',4',7-TrihydroxyisoflavoneCAS# 485-63-2 |
Quality Control & MSDS
Number of papers citing our products
Chemical structure
3D structure
Cas No. | 485-63-2 | SDF | Download SDF |
PubChem ID | 5284648 | Appearance | Powder |
Formula | C15H10O5 | M.Wt | 270.2 |
Type of Compound | Flavonoids | Storage | Desiccate at -20°C |
Solubility | Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc. | ||
Chemical Name | 3-(3,4-dihydroxyphenyl)-7-hydroxychromen-4-one | ||
SMILES | C1=CC(=C(C=C1C2=COC3=C(C2=O)C=CC(=C3)O)O)O | ||
Standard InChIKey | DDKGKOOLFLYZDL-UHFFFAOYSA-N | ||
Standard InChI | InChI=1S/C15H10O5/c16-9-2-3-10-14(6-9)20-7-11(15(10)19)8-1-4-12(17)13(18)5-8/h1-7,16-18H | ||
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. |
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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. |
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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. |
Description | 3',4',7-Trihydroxyisoflavone has antioxidant, estrogenic, and chemoprotective activities, it inhibits the CK-II-mediated phosphorylation of 60S acidic ribosomal P proteins in vitro. CDKs and PI3K are the primary molecular targets of 3',4',7-Trihydroxyisoflavone in the suppression of EGF-induced cell proliferation. 3',4',7-Trihydroxyisoflavone nanoparticles are characterized by improved physicochemical properties, increased water solubility, and enhanced skin penetration, and these may have potential use in the future as a topical delivery formulation for the treatment of skin diseases. |
3',4',7-Trihydroxyisoflavone Dilution Calculator
3',4',7-Trihydroxyisoflavone Molarity Calculator
1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
1 mM | 3.701 mL | 18.5048 mL | 37.0096 mL | 74.0192 mL | 92.5241 mL |
5 mM | 0.7402 mL | 3.701 mL | 7.4019 mL | 14.8038 mL | 18.5048 mL |
10 mM | 0.3701 mL | 1.8505 mL | 3.701 mL | 7.4019 mL | 9.2524 mL |
50 mM | 0.074 mL | 0.3701 mL | 0.7402 mL | 1.4804 mL | 1.8505 mL |
100 mM | 0.037 mL | 0.185 mL | 0.3701 mL | 0.7402 mL | 0.9252 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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Pharmacological chaperones increase residual beta-galactocerebrosidase activity in fibroblasts from Krabbe patients.[Pubmed:24913062]
Mol Genet Metab. 2014 Aug;112(4):294-301.
Krabbe disease or globoid cell leukodystrophy is a degenerative, lysosomal storage disease resulting from the deficiency of beta-galactocerebrosidase activity. This enzyme catalyzes the lysosomal hydrolysis of galactocerebroside and psychosine. Krabbe disease is inherited as an autosomal recessive trait, and many of the 70 disease-causing mutations identified in the GALC gene are associated with protein misfolding. Recent studies have shown that enzyme inhibitors can sometimes translocate misfolded polypeptides to their appropriate target organelle bypassing the normal cellular quality control machinery and resulting in enhanced activity. In search for pharmacological chaperones that could rescue the beta-galactocerebrosidase activity, we investigated the effect of alpha-Lobeline or 3',4',7-trihydroxyisoflavone on several patient-derived fibroblast cell lines carrying missense mutations, rather than on transduced cell lines. Incubation of these cell lines with alpha-lobeline or 3',4',7-trihydroxyisoflavone leads to an increase of beta-galacocerebrosidase activity in p.G553R + p.G553R, in p.E130K + p.N295T and in p.G57S + p.G57S mutant forms over the critical threshold. The low but sustained expression of beta-galactocerebrosidase induced by these compounds is a promising result; in fact, it is known that residual enzyme activity of only 15-20% is sufficient for clinical efficacy. The molecular interaction of the two chaperones with beta-galactocerebrosidase is also supported by in silico analysis. Collectively, our combined in silico-in vitro approach indicate alpha-lobeline and 3',4',7-trihydroxyisoflavone as two potential pharmacological chaperones for the treatment or improvement of quality of life in selected Krabbe disease patients.
Production of a novel O-methyl-isoflavone by regioselective sequential hydroxylation and O-methylation reactions in Streptomyces avermitilis host system.[Pubmed:23592181]
Biotechnol Bioeng. 2013 Oct;110(10):2591-9.
Distinct isoflavone O-methyltransferases (IOMTs) from Streptomyces species were isolated and expressed using S. avermitilis host system. Previously reported isoflavone 7-O-methyltransferases (I7OMTs, E.C. 2.1.1.150) and two putative O-methyltransferases (OMTs) from Saccharopolyspora erythraea were selected by comparative sequence grouping and expressed in S. avermitilisDeltaSaOMT2 under the control of constitutive ermE promoter. During whole-cell biotransformation of 4',7-dihydroxyisoflavone (daidzein) by constructed recombinant strains, production of O-methylated daidzein was investigated. S. avermitilisDeltaSaOMT2::SeOMT3 (SeOMT3) produced 7-methoxy-4'-hydroxyisoflavone (7-OMD) with 4.5% of low conversion yield due to competitive oxidation reactions. However, SeOMT3 could produce a novel 4',7-dihydroxy-3'-methoxyisoflavone (3'-OMD) (<1%) resulted from subsequent 3'-O-methylation of 3',4',7-trihydroxyisoflavone (3'-OHD) which was a hydroxylated product catalyzed by oxygenases. Although external addition of SAM did not change the conversion yield of O-methylation reaction, co-expression of SAM synthetase gene (metK) with SeOMT3 greatly induced the regiospecific O-methylation reaction at 3'-hydroxyl group with final conversion of 12.1% using 0.1 mM of daidzein.
Transcriptomic study for screening genes involved in the oxidative bioconversions of Streptomyces avermitilis.[Pubmed:23474968]
Bioprocess Biosyst Eng. 2013 Nov;36(11):1621-30.
Streptomyces avermitilis is a well known organism producing avermectin antibiotics, and has been utilized as an industrial host for oxidation bioconversion processes. Recently, gene screening strategies related to bioconversions have received much focus, as attempts are made to optimize oxidation and biodegradation pathways to maximize yield and productivity. Here, we have demonstrated the oxidative metabolisms of three molecules, daidzein, p-coumaric acid and mevastatin, where S. avermitilis converted each substrate to 3',4',7-trihydroxyisoflavone, caffeic acid and hydroxyl-mevastatin to yield 9.3, 32.5 and 15.0 %, respectively. Microarray technology was exploited to investigate genome-wide analysis of gene expression changes, which were induced upon the addition of each substrate. Cytochrome P450 hydroxylases (pteC, cyp28 and olmB), diooxygenases (xylE, cdo1 and putatives) and LuxAB-like oxygenase were identified. One of them, cyp28, was indeed a gene encoding P450 hydroxylase responsible for the oxidative reaction of daidzein. Furthermore, possible electron transfer chain (fdrC --> pteE --> pteC) supporting cytochrome P450 dependent hydroxylation of daidzein has been suggested based on the interpretation of expression profiles. The result provided a potential application of transcriptomic study on uncovering enzymes involved in oxidative bioconversions of S. avermitilis.
Inhibitory effects of isoflavonoids on rat prostate testosterone 5alpha-reductase.[Pubmed:23265084]
J Acupunct Meridian Stud. 2012 Dec;5(6):319-22.
Testosterone 5alpha-reductase inhibitors represent important therapeutic drugs for use against androgen-dependent diseases such as benign prostatic hyperplasia, male pattern baldness, and acne. We have searched for inhibitors of rat prostate testosterone 5alpha-reductase in the cultured broths of many kinds of soil bacteria, and have found that cultured soybean-casein digest broths of certain bacterial strains have a potent inhibitory effect on the enzyme. We tested 10 selected isoflavonoids, including isoflavones and O-methylated isoflavones, for inhibitory effects on rat prostate testosterone 5alpha-reductase to determine the important structural elements for inhibition of the enzyme. Genistein, biochanin A, equol, and 3',4',7-trihydroxyisoflavone showed considerably higher inhibitory effects whereas daidzein, formononetin, glycitein, prunetin, ipriflavone, and 4',7-dimethoxyisoflavone showed lower inhibitory effects. The IC(50) values of genistein, biochanin A, equol, 3',4',7-trihydroxyisoflavone, and riboflavin, a positive control, for rat prostate testosterone 5alpha-reductase were 710 mum, 140 mum, 370 mum, 690 mum, and 17 mum, respectively. Daidzein, genistein, biochanin A, formononetin, and equol are already known to be testosterone 5alpha-reductase inhibitors, but this is the first characterization of 3',4',7-trihydroxyisoflavone as an inhibitor of the enzyme.
A-ring ortho-specific monohydroxylation of daidzein by cytochrome P450s of Nocardia farcinica IFM10152.[Pubmed:19918785]
Biotechnol J. 2009 Nov;4(11):1586-95.
The bioconversion of the isoflavonoid daidzein using whole cell Nocardia farcinica IFM10152 showed two kinds of major metabolic modifications, i.e. mono-hydroxylation and subsequent O-methylation. The major hydroxylated products of daidzein prior to the O-methylation reaction were 3',4',7-trihydroxyisoflavone (3'-ODI), 4',6,7-trihydroxyisoflavone (6-ODI) and 4',7,8-trihydroxyisoflavone (8-ODI), which are mono-hydroxylated at the ortho position of each hydroxyl group of daidzein. To identify monooxygenases playing a key role in the monohydroxylation of the A-ring of daidzein, all genes of 27 cytochrome P450s from N. farcinica IFM10152 were cloned and transformed into a E. coli BL21 (DE3) host system. By this enzymatic reaction using the mutants and the genome sequence analysis of N. farcinica IFM10152, it was revealed that nfa12130 and nfa33880 P450 genes clustered with their own ferredoxins and ferredoxin reductases (nfa12140+nfa12150 and nfa338870+nfa33860, respectively) are responsible for the hydroxylation of the A-ring of daidzein, and their major reaction products were 6-ODI and 8-ODI, respectively.
Regioselective hydroxylation of isoflavones by Streptomyces avermitilis MA-4680.[Pubmed:19577190]
J Biosci Bioeng. 2009 Jul;108(1):41-6.
Screening of bacterial whole cells was performed for regioselective hydroxylation of daidzein and genistein. Among the strains examined, Streptomyces avermitilis MA-4680 showed high ortho-dihydroxylation activity to produce 3',4',7-trihydroxyisoflavone and 3',4',5,7-tetrahydroxyisoflavone from daidzein (4',7-dihydroxyisoflavone) and genistein (4',5,7-trihydroxyisoflavone), respectively. Using 100 mg cells (wet wt.) and 1% (v/v) Triton X100 in 1 ml of total reaction volume, where 100 microl of the substrate solution (0.5 mM in 10% (v/v) mixed solvent of DMSO:MeOH = 3:7) was added to 900 microl of potassium phosphate buffer (100 mM, pH 7.2), a 16% molar conversion yield of 3',4',7-trihydroxyisoflavone was obtained from 0.5 mM daidzein after 24 h of reaction time at 28 degrees C and 200 rpm. Ketoconazole significantly (ca. 90%) inhibited the ortho-hydroxylation activity of daidzein, suggesting that cytochrome P450 enzymes putatively play roles in regiospecific daidzein hydroxylation. The analysis of the reaction products was determined by gas chromatography/mass spectrometry (GC/MS) and (1)H NMR.