Naringenin triacetateCAS# 3682-04-0 |
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| Cas No. | 3682-04-0 | SDF | Download SDF |
| PubChem ID | 14354984 | Appearance | Powder |
| Formula | C21H18O8 | M.Wt | 398.4 |
| Type of Compound | Flavonoids | Storage | Desiccate at -20°C |
| Solubility | Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc. | ||
| Chemical Name | [4-(5,7-diacetyloxy-4-oxo-2,3-dihydrochromen-2-yl)phenyl] acetate | ||
| SMILES | CC(=O)OC1=CC=C(C=C1)C2CC(=O)C3=C(C=C(C=C3O2)OC(=O)C)OC(=O)C | ||
| Standard InChIKey | HQZXCNZZVRAEPO-UHFFFAOYSA-N | ||
| Standard InChI | InChI=1S/C21H18O8/c1-11(22)26-15-6-4-14(5-7-15)18-10-17(25)21-19(28-13(3)24)8-16(27-12(2)23)9-20(21)29-18/h4-9,18H,10H2,1-3H3 | ||
| 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. Naringenin triacetate exhibits a better binding affinity with multiple crystal structures of first bromodomain BRD4 (BRD4 BD1) when compared with the known inhibitors. |
Naringenin triacetate Dilution Calculator
Naringenin triacetate Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 2.51 mL | 12.5502 mL | 25.1004 mL | 50.2008 mL | 62.751 mL |
| 5 mM | 0.502 mL | 2.51 mL | 5.0201 mL | 10.0402 mL | 12.5502 mL |
| 10 mM | 0.251 mL | 1.255 mL | 2.51 mL | 5.0201 mL | 6.2751 mL |
| 50 mM | 0.0502 mL | 0.251 mL | 0.502 mL | 1.004 mL | 1.255 mL |
| 100 mM | 0.0251 mL | 0.1255 mL | 0.251 mL | 0.502 mL | 0.6275 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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Effect of non-beta-lactams on stable variants of inhibitor-resistant TEM beta-lactamase in uropathogenic Escherichia coli: implication for alternative therapy.[Pubmed:29247576]
J Appl Microbiol. 2018 Mar;124(3):667-681.
AIMS: beta-lactamase inhibitor resistance (BLIR) among the uropathogenic Escherichia coli (UPEC) minimizes treatment options. This study aimed to identify inhibitor-resistant TEM (IRT) beta-lactamase that impart BLIR phenotype and explore non-beta-lactams as alternative therapeutics. METHODS AND RESULTS: Thirty BLIR UPEC isolates were detected by Kirby-Bauer disc diffusion technique using beta-lactam-beta-lactamase inhibitor combination. Conjugal transfer of BLIR was successful from 17 isolates. PCR and sequencing of the TEM beta-lactamases from the transconjugants indicated 14 TEM-84 (IRT) and three novel IRT variants (pUE184TEM, pUE203TEM, pUE210TEM). Three-dimensional models of the latter were predicted and validated. Molecular docking of selected non-beta-lactams (morin, catechin, Naringenin triacetate) with the variants using AutoDock 4.2 showed comparable docking scores with significant hydrogen bond and hydrophobic interactions. Molecular dynamics simulation study confirmed stability of the non-beta-lactams inside the catalytic pocket of the enzymes. Moreover, all three non-beta-lactams were found to inhibit the purified TEM beta-lactamase variants in vitro. Microbroth dilution method indicated Naringenin triacetate 64 mug ml(-1) in combination with ceftazidime (CAZ) 30 mug ml(-1) to be most effective against the BLIR transconjugants. CONCLUSIONS: BLIR phenotypes were primarily attributed to the production of IRT beta-lactamases. Administration of the non-beta-lactams with CAZ demonstrated an alternative therapeutic strategy against the IRT beta-lactamase producers. SIGNIFICANCE AND IMPACT OF THE STUDY: This study indicates high risk of transmission of IRT beta-lactamases and suggests beta-lactam-non-beta-lactam combination therapy to combat BLIR.
Simple Synthesis of Sakuranetin and Selinone via a Common Intermediate, Utilizing Complementary Regioselectivity in the Deacetylation of Naringenin Triacetate.[Pubmed:27373654]
Chem Pharm Bull (Tokyo). 2016;64(7):961-5.
Sakuranetin and selinone were successfully synthesized utilizing the regioselective deacetylation of Naringenin triacetate. Deacetylation of the latter at C-7 with imidazole in 1,4-dioxane at 40 degrees C furnished the corresponding diacetate in 80% yield. Methylation of the obtained free hydroxy group and subsequent removal of the remaining two acetyl groups gave sakuranetin, which was previously isolated as a phytoalexin against rice blast disease fungus, Pyricularia oryzae, in 71% overall yield. The same intermediate, Naringenin triacetate, was subjected to transesterification with 2-propanol in tetrahydrofuran, catalyzed by Candida antarctica lipase B. A contrasting regioselective preference for C-4' deacetylation was observed, giving an isomeric diacetate in 82% yield. Prenylation of the free hydroxy group under Mitsunobu conditions and subsequent deprotection furnished selinone, which was previously isolated from Monotes engleri and exhibits antifungal activity against Candida albicans, in 55% overall yield.
