6-PrenylnaringeninCAS# 68236-13-5 |
- (S)-4',5,7-Trihydroxy-6-prenylflavanone
Catalog No.:BCN0338
CAS No.:68682-01-9
Quality Control & MSDS
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| Cas No. | 68236-13-5 | SDF | Download SDF |
| PubChem ID | 155094 | Appearance | Powder |
| Formula | C20H20O5 | M.Wt | 340.4 |
| Type of Compound | Flavonoids | Storage | Desiccate at -20°C |
| Synonyms | (2S)-6-Prenylnaringenin | ||
| Solubility | Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc. | ||
| Chemical Name | (2S)-5,7-dihydroxy-2-(4-hydroxyphenyl)-6-(3-methylbut-2-enyl)-2,3-dihydrochromen-4-one | ||
| SMILES | CC(=CCC1=C(C=C2C(=C1O)C(=O)CC(O2)C3=CC=C(C=C3)O)O)C | ||
| Standard InChIKey | YHWNASRGLKJRJJ-KRWDZBQOSA-N | ||
| 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 | 1. 6-Prenylnaringenin is an isomer of the potent phytoestrogen, 8-prenylnaringenin. 2. 6-Prenylnaringenin and 8-prenylnaringenin have anti-cancer potential , dose-dependent reduction of cellular proliferation of human PC-3 prostate cancer and UO.31 renal carcinoma cells upon treatment 3. 6-Prenylnaringenin can inhibit 12-O-tetradecanoylphorbol 13-acetate (TPA)-induced inflammation (1μg/ear) in mice, it also exhibits inhibitory effects on skin-tumor promotion in anin vivo two-stagemouse-skin carcinogenesis test based on 7,12-dimethylbenz[a]- anthracene (DMBA) as initiator and with TPA as promoter. 4. 6-Prenylnaringenin exhibits both mixed and non-competitive inhibitory characteristics against tyrosinase, tyrosinase is the rate-limiting enzyme for the production of melanin and other pigments via the oxidation of l-tyrosine. |
| Targets | Tyrosinase |
6-Prenylnaringenin Dilution Calculator
6-Prenylnaringenin Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 2.9377 mL | 14.6886 mL | 29.3772 mL | 58.7544 mL | 73.443 mL |
| 5 mM | 0.5875 mL | 2.9377 mL | 5.8754 mL | 11.7509 mL | 14.6886 mL |
| 10 mM | 0.2938 mL | 1.4689 mL | 2.9377 mL | 5.8754 mL | 7.3443 mL |
| 50 mM | 0.0588 mL | 0.2938 mL | 0.5875 mL | 1.1751 mL | 1.4689 mL |
| 100 mM | 0.0294 mL | 0.1469 mL | 0.2938 mL | 0.5875 mL | 0.7344 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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Anti-inflammatory and anti-tumor-promoting effects of 5-deprenyllupulonol C and other compounds from Hop (Humulus lupulus L.).[Pubmed:22700224]
Chem Biodivers. 2012 Jun;9(6):1045-54.
A new phloroglucinol derivative, 5-deprenyllupulonol C (1), along with four other phloroglucinol derivatives, 2-5, five chalcones, 6-10, four flavanones, 11-14, two flavonol glycosides, 15 and 16, and five triterpenoids, 17-21, were isolated from the female inflorescence pellet extracts of hop (Humulus lupulus L.). Upon evaluation of these compounds against the Epstein-Barr virus early antigen (EBV-EA) activation induced by 12-O-tetradecanoylphorbol 13-acetate (TPA) in Raji cells, twelve compounds, i.e., 1-4, 11-14, 17-19, and 21, showed potent inhibitory effects on EBV-EA induction, with IC(5)(0) values in the range of 215-393 mol ratio/32 pmol TPA. In addition, eleven compounds, i.e., 1-4, 6, 11, 12, 14, 17, 18, and 20, were found to inhibit TPA-induced inflammation (1 mug/ear) in mice, with ID(5)(0) values in the range of 0.13-1.06 mumol per ear. Further, lupulone C (2) and 6-Prenylnaringenin (14) exhibited inhibitory effects on skin-tumor promotion in an in vivo two-stage mouse-skin carcinogenesis test based on 7,12-dimethylbenz[a]anthracene (DMBA) as initiator and with TPA as promoter.
Phenols displaying tyrosinase inhibition from Humulus lupulus.[Pubmed:26162028]
J Enzyme Inhib Med Chem. 2016 Oct;31(5):742-7.
Tyrosinase is the rate-limiting enzyme for the production of melanin and other pigments via the oxidation of l-tyrosine. The methanol extract from Humulus lupulus showed potent inhibition against mushroom tyrosinase. The bioactivity-guided fractionation of this methanol extract resulted in the isolation of seven flavonoids (1-7), identified as xanthohumol (1), 4'-O-methylxanthohumol (2), xanthohumol C (3), flavokawain C (4), xanthoumol B (5), 6-Prenylnaringenin (6) and isoxanthohumol (7). All isolated flavonoids (1-7) effectively inhibited the monophenolase (IC50s = 15.4-58.4 microM) and diphenolase (IC50s = 27.1-117.4 microM) activities of tyrosinase. Kinetic studies using Lineweaver-Burk and Dixon-plots revealed that chalcones (1-5) were competitive inhibitors, whereas flavanones (6 and 7) exhibited both mixed and non-competitive inhibitory characteristics. In conclusion, this study is the first to demonstrate that the phenolic phytochemicals of H. lupulus display potent inhibitory activities against tyrosinase.
