Robinetin

CAS# 490-31-3

Robinetin

Catalog No. BCN5596----Order now to get a substantial discount!

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Chemical structure

Robinetin

3D structure

Chemical Properties of Robinetin

Cas No. 490-31-3 SDF Download SDF
PubChem ID 5281692 Appearance Yellow powder
Formula C15H10O7 M.Wt 302.2
Type of Compound Flavonoids Storage Desiccate at -20°C
Synonyms Norkanugin; 3,3',4',5',7-Pentahydroxyflavone
Solubility Soluble in chloroform and DMSO
Chemical Name 3,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)chromen-4-one
SMILES C1=CC2=C(C=C1O)OC(=C(C2=O)O)C3=CC(=C(C(=C3)O)O)O
Standard InChIKey SOEDEYVDCDYMMH-UHFFFAOYSA-N
Standard InChI InChI=1S/C15H10O7/c16-7-1-2-8-11(5-7)22-15(14(21)12(8)19)6-3-9(17)13(20)10(18)4-6/h1-5,16-18,20-21H
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 Robinetin

The leaves of Robinia pseudacacia

Biological Activity of Robinetin

Description1. Robinetin has antioxidant and antiradical activities, inhibits EYPC membrane lipid peroxidation and HbA glycosylation with high efficiency. 2. Robinetin leads to the occurrence of positive induced circular dichroism (ICD) bands in the near ultra-violet (UV) region. 3. Robinetin has anti-mutagenesis and anti-promotion effects, diminishes ornithine decarboxylase activity induction at 6 h after 12-O-tetradecanoyl phorbol-13-acetate.
TargetsHIV

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Preparing Stock Solutions of Robinetin

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 3.3091 mL 16.5453 mL 33.0907 mL 66.1813 mL 82.7267 mL
5 mM 0.6618 mL 3.3091 mL 6.6181 mL 13.2363 mL 16.5453 mL
10 mM 0.3309 mL 1.6545 mL 3.3091 mL 6.6181 mL 8.2727 mL
50 mM 0.0662 mL 0.3309 mL 0.6618 mL 1.3236 mL 1.6545 mL
100 mM 0.0331 mL 0.1655 mL 0.3309 mL 0.6618 mL 0.8273 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 Robinetin

Binding of the bioflavonoid robinetin with model membranes and hemoglobin: Inhibition of lipid peroxidation and protein glycosylation.[Pubmed:19914085]

J Photochem Photobiol B. 2010 Jan 21;98(1):12-9.

Recent years have witnessed burgeoning interest in plant flavonoids as novel therapeutic drugs targeting cellular membranes and proteins. Motivated by this scenario, we explored the binding of Robinetin (3,7,3',4',5'-pentahydroxyflavone, a bioflavonoid with remarkable 'two color' intrinsic fluorescence properties), with egg yolk phosphatidylcholine (EYPC) liposomes and normal human hemoglobin (HbA), using steady state and time resolved fluorescence spectroscopy. Distinctive fluorescence signatures obtained for Robinetin indicate its partitioning (K(p)=8.65x10(4)) into the hydrophobic core of the membrane lipid bilayer. HbA-Robinetin interaction was examined using both Robinetin fluorescence and flavonoid-induced quenching of the protein tryptophan fluorescence. Specific interaction with HbA was confirmed from three lines of evidence: (a) bimolecular quenching constant K(q)>>diffusion controlled limit; (b) closely matched values of Stern-Volmer quenching constant and binding constant; (c) tau(0)/tau=1 (where tau(0) and tau are the unquenched and quenched tryptophan fluorescence lifetimes, respectively). Absorption spectrophotometric assays reveal that Robinetin inhibits EYPC membrane lipid peroxidation and HbA glycosylation with high efficiency.

Anti-mutagenesis and anti-promotion by apigenin, robinetin and indole-3-carbinol.[Pubmed:3708757]

Carcinogenesis. 1986 Jun;7(6):959-63.

We assessed the anti-mutagenic and anti-promotion properties of two flavones, apigenin and Robinetin, and of indole-3-carbinol, because these compounds have been reported in vegetables, the consumption of which has been associated with reduced rates of cancer. However, the active components of these foods and their effects on carcinogenesis have not been established. Anti-mutagenicity was determined in the Salmonella typhimurium assay by measuring the effects of the test compounds on bacterial mutagenesis induced by methyl-nitrosourea (MNU), methyl-n-nitro-N-nitrosoguanidine (MNNG), benzo[a]pyrene (BaP) or 2-aminoanthracene (2-AA). Inclusion of apigenin resulted in a 62% and a 43% inhibition of mutagenicity with 13 nmol of 2-AA and 30 nmol BaP respectively. Robinetin caused an 87% inhibition of mutagenicity by 2-AA, but indole-3-carbinol had little or no effect on the mutagenicity of any of the compounds. None of the three compounds inhibited mutagenesis by MNU or MNNG and none were mutagenic or toxic when tested in the absence of mutagenic compounds at doses up to 20 micrograms/plate. Anti-promotion properties were assessed by measuring the effects of apigenin, Robinetin and indole-3-carbinol on induction of ornithine decarboxylase activity (ODC) in mouse epidermis by 17 nmol 12-O-tetradecanoyl phorbol-13-acetate (TPA). Pretreatment of the skin half an hour before TPA with apigenin, Robinetin, butylated hydroxyanisole, 13-cis-retinoic acid (all at 50 mumol) or di-fluoromethylornithine (1.6 mumol) inhibited ODC induction at 6 h after TPA by 67-80%. Pretreatment with 50 mumol indole-3-carbinol caused a 78% elevation in the TPA induction at this time. Dose response measurements were conducted with apigenin, indole-3-carbinol and Robinetin. Inhibition by 30-90% of TPA-induced ODC was observed at 6 h after TPA in mice pretreated with 12.5-100 mumol apigenin. Pretreatment with 37.5 or 50 mumol indole-3-carbinol or 0.5, 12.5 or 25 mumol Robinetin resulted in elevated induction of epidermal ODC by TPA at 6 h after TPA. However, treatment with 50 or 100 mumol Robinetin diminished ODC induction at 6 h after TPA. Treatment with 100 mumol apigenin or 50 or 100 mumol indole-3-carbinol in non-TPA-treated mouse skin caused elevations in epidermal ODC. In comparing the time course of ODC induction, indole-3-carbinol (50 mumol) pretreatment shifted the induction of epidermal ODC to earlier times, in addition to elevating ODC induction by TPA.(ABSTRACT TRUNCATED AT 400 WORDS)

Effect of beta-cyclodextrin nanocavity confinement on the photophysics of robinetin.[Pubmed:17951065]

J Photochem Photobiol B. 2007 Dec 14;89(2-3):88-97.

We have studied the confinement of Robinetin, a therapeutically active plant flavonol, in cyclodextrin (CDx) nanocavities, using steady state and time resolved fluorescence spectroscopy. Enhanced tautomer emission (arising from excited state intramolecular proton transfer (ESIPT)) as well as dramatically blue shifted (approximately 10 nm in beta-CDx and approximately 33 nm in SHP beta-CDx) normal fluorescence observed upon addition of the beta-CDxs indicate that Robinetin readily enters the doughnut-shaped hydrophobic cavity of beta-CDx where the chromone moiety is well shielded from external hydrogen bonding perturbations. Detailed analyses of the fluorescence data (emission profile, anisotropy, decay times) indicate that Robinetin forms 1:1 inclusion complexes with both natural and chemically modified beta-cyclodextrins (beta-CDx and SHP beta-CDx) with affinity constant values K=195+/-17 M(-1) and 1055+/-48 M(-1) respectively, indicating the prospective utility of SHP beta-CDx in particular as an effective drug carrier. Unlike beta-CDxs, alpha-CDxs do not form inclusion complexes with Robinetin. To further characterize the Robinetin/beta-CDxs complexes, circular dichroism (CD) spectroscopic studies have been performed, which reveal that incorporation of Robinetin molecules in the chiral environment of the beta-CDxs strongly affects the electronic transitions of Robinetin leading to the occurrence of positive induced circular dichroism (ICD) bands in the near ultra-violet (UV) region. Molecular mechanics calculations show that the inclusion complex with the chromone ring inserted into the beta-CDx cavity is most favorable, in agreement with our spectroscopic data.

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