Laurolitsine

CAS# 5890-18-6

Laurolitsine

Catalog No. BCN2634----Order now to get a substantial discount!

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Quality Control of Laurolitsine

Number of papers citing our products

Chemical structure

Laurolitsine

3D structure

Chemical Properties of Laurolitsine

Cas No. 5890-18-6 SDF Download SDF
PubChem ID 22179 Appearance Cryst.
Formula C18H19NO4 M.Wt 313.34
Type of Compound Alkaloids Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name (6aS)-1,10-dimethoxy-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline-2,9-diol
SMILES COC1=C(C=C2CC3C4=C(C2=C1)C(=C(C=C4CCN3)O)OC)O
Standard InChIKey KYVJVURXKAZJRK-LBPRGKRZSA-N
Standard InChI InChI=1S/C18H19NO4/c1-22-15-8-11-10(7-13(15)20)5-12-16-9(3-4-19-12)6-14(21)18(23-2)17(11)16/h6-8,12,19-21H,3-5H2,1-2H3/t12-/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.
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 Laurolitsine

The roots of Lindera aggregata (Sims) Kosterm

Protocol of Laurolitsine

Structure Identification
J Nat Prod. 2013 Mar 22;76(3):405-12.

Semisynthesis and myocardial activity of thaliporphine N-homologues.[Pubmed: 23305495]

The N-homologues and optical isomers of thaliporphine (5a), a potent antiarrhythmic agent, were prepared starting from Laurolitsine (1), an abundant aporphine present in Phoebe formosana.
METHODS AND RESULTS:
Treating N-propylnorglaucine with 90% H2SO4 yielded one additional product, an 11-sulfonyl-1,11-anhydroaporphine. Reaction of N-formylnorglaucine (3a) with 90% H2SO4, however, yielded the 9-sulfonyl-seco product as a major product. Treatment of 3a with 98% H2SO4 yielded pancordine (10), which, upon catalytic hydrogenation, yielded (±)-wilsonirine. (1)H NMR spectroscopic analysis was applied successfully to monitor the optical purity of the crystalline salt while undertaking optical resolution.
CONCLUSIONS:
Thaliporphine (5a) was demonstrated to possess better positive inotropic and less negative chronotropic effects than the left-hand optical isomer and showed the best activity on rat cardiac tissue among the N-homologues prepared.

Laurolitsine Dilution Calculator

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Laurolitsine Molarity Calculator

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Preparing Stock Solutions of Laurolitsine

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 3.1914 mL 15.9571 mL 31.9142 mL 63.8284 mL 79.7855 mL
5 mM 0.6383 mL 3.1914 mL 6.3828 mL 12.7657 mL 15.9571 mL
10 mM 0.3191 mL 1.5957 mL 3.1914 mL 6.3828 mL 7.9786 mL
50 mM 0.0638 mL 0.3191 mL 0.6383 mL 1.2766 mL 1.5957 mL
100 mM 0.0319 mL 0.1596 mL 0.3191 mL 0.6383 mL 0.7979 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 Laurolitsine

Semisynthesis and myocardial activity of thaliporphine N-homologues.[Pubmed:23305495]

J Nat Prod. 2013 Mar 22;76(3):405-12.

The N-homologues and optical isomers of thaliporphine (5a), a potent antiarrhythmic agent, were prepared starting from Laurolitsine (1), an abundant aporphine present in Phoebe formosana. Treating N-propylnorglaucine with 90% H2SO4 yielded one additional product, an 11-sulfonyl-1,11-anhydroaporphine. Reaction of N-formylnorglaucine (3a) with 90% H2SO4, however, yielded the 9-sulfonyl-seco product as a major product. Treatment of 3a with 98% H2SO4 yielded pancordine (10), which, upon catalytic hydrogenation, yielded (+/-)-wilsonirine. (1)H NMR spectroscopic analysis was applied successfully to monitor the optical purity of the crystalline salt while undertaking optical resolution. Thaliporphine (5a) was demonstrated to possess better positive inotropic and less negative chronotropic effects than the left-hand optical isomer and showed the best activity on rat cardiac tissue among the N-homologues prepared.

Description

Laurolitsine ((+)-Norboldine) is an alkaloid isolated from the leaves of Peumus boldus Molina.

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