CanadineCAS# 5096-57-1 |
- Tetrahydroberberine
Catalog No.:BCN2648
CAS No.:522-97-4
Quality Control & MSDS
Number of papers citing our products
Chemical structure
3D structure
| Cas No. | 5096-57-1 | SDF | Download SDF |
| PubChem ID | 21171 | Appearance | Powder |
| Formula | C20H21NO4 | M.Wt | 339.4 |
| Type of Compound | Alkaloids | Storage | Desiccate at -20°C |
| Solubility | Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc. | ||
| SMILES | COC1=C(C2=C(CC3C4=CC5=C(C=C4CCN3C2)OCO5)C=C1)OC | ||
| Standard InChIKey | VZTUIEROBZXUFA-INIZCTEOSA-N | ||
| Standard InChI | InChI=1S/C20H21NO4/c1-22-17-4-3-12-7-16-14-9-19-18(24-11-25-19)8-13(14)5-6-21(16)10-15(12)20(17)23-2/h3-4,8-9,16H,5-7,10-11H2,1-2H3/t16-/m0/s1 | ||
| 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. Canadine has antioxidant activity with low-toxic effect. |
| Targets | P450 (e.g. CYP17) |
Canadine Dilution Calculator
Canadine Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 2.9464 mL | 14.7319 mL | 29.4638 mL | 58.9275 mL | 73.6594 mL |
| 5 mM | 0.5893 mL | 2.9464 mL | 5.8928 mL | 11.7855 mL | 14.7319 mL |
| 10 mM | 0.2946 mL | 1.4732 mL | 2.9464 mL | 5.8928 mL | 7.3659 mL |
| 50 mM | 0.0589 mL | 0.2946 mL | 0.5893 mL | 1.1786 mL | 1.4732 mL |
| 100 mM | 0.0295 mL | 0.1473 mL | 0.2946 mL | 0.5893 mL | 0.7366 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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Cloning and characterization of canadine synthase involved in noscapine biosynthesis in opium poppy.[Pubmed:24316226]
FEBS Lett. 2014 Jan 3;588(1):198-204.
Noscapine biosynthesis in opium poppy is thought to occur via N-methylCanadine, which would be produced through 9-O-methylation of (S)-scoulerine, methylenedioxy bridge formation on (S)-tetrahydrocolumbamine, and N-methylation of (S)-Canadine. Only scoulerine 9-O-methyltransferase has been functionally characterized. We report the isolation and characterization of a cytochrome P450 (CYP719A21) from opium poppy that converts (S)-tetrahydrocolumbamine to (S)-Canadine. Recombinant CYP719A21 displayed strict substrate specificity and high affinity (Km=4.63+/-0.71 muM) for (S)-tetrahydrocolumbamine. Virus-induced gene silencing of CYP719A21 caused a significant increase in (S)-tetrahydrocolumbamine accumulation and a corresponding decrease in the levels of putative downstream intermediates and noscapine in opium poppy plants.
Antioxidant and cytotoxic activities of canadine: biological effects and structural aspects.[Pubmed:18295494]
Bioorg Med Chem. 2008 Apr 1;16(7):3641-51.
The cytotoxic effects of four alkaloids, berberine, Canadine, anonaine, and antioquine were evaluated using three different cell cultures, a primary culture (rat hepatocytes) and two cell lines (HepG2 and HeLa). Our results indicate that berberine, anonaine, and antioquine possess a significant the cytotoxic effect. In contrast, Canadine does not possess cytotoxic effect at concentrations tested here. A molecular modeling study indicates that the quaternary nitrogen, the aromatic polycyclic and planar structure of berberine could be the pharmacophoric patron to produce the cytotoxic effect. In parallel our results demonstrated that Canadine possess a significant antioxidant activity. Stereoelectronic aspects of this alkaloid were found to be closely related to those displayed by alpha-tocopherol and its water-soluble analogue trolox. The antioxidant activities of Canadine, combined with its low-toxic effect, indicated that the potential of this alkaloid as a novel class of antioxidant agent is very interesting and deserves further research.
