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Catalog No. BCN3204
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20mg $298 In stock
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Quality Control of 13-Hydroxylupanine

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Chemical Properties of 13-Hydroxylupanine

Cas No. 15358-48-2 SDF Download SDF
SMILES C1C[C@@H]2[C@H]3C[C@@H](CN2C(=O)C1)[C@@H]4C[C@H](CCN4C3)O
Standard InChI InChI=1S/C15H24N2O2/c18-12-4-5-16-8-10-6-11(14(16)7-12)9-17-13(10)2-1-3-15(17)19/h10-14,18H,1-9H2/t10-,11-,12-,13+,14-/m0/s1
Type of Compound Alkaloids Appearance Powder
Formula C15H24N2O2 M.Wt 264.4
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
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.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other courier with RT , or blue ice upon request.

Preparing Stock Solutions of 13-Hydroxylupanine

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 3.7821 mL 18.9107 mL 37.8215 mL 75.643 mL 94.5537 mL
5 mM 0.7564 mL 3.7821 mL 7.5643 mL 15.1286 mL 18.9107 mL
10 mM 0.3782 mL 1.8911 mL 3.7821 mL 7.5643 mL 9.4554 mL
50 mM 0.0756 mL 0.3782 mL 0.7564 mL 1.5129 mL 1.8911 mL
100 mM 0.0378 mL 0.1891 mL 0.3782 mL 0.7564 mL 0.9455 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.

Preparation of 13-Hydroxylupanine

This product is isolated and purified from the herbs of Cytisus scoparius

References on 13-Hydroxylupanine

Disposition of lupanine and 13-hydroxylupanine in man.[Pubmed: 7810174]

1. The in vivo disposition of lupanine and 13-Hydroxylupanine was studied in subjects identified as poor metabolizers (PM, n = 4) and extensive metabolizers (EM, n = 7) phenotypes for cytochrome P4502D6 (CYP2D6). 2. After oral administration (40.26 mumol), the half-life (t1/2) of lupanine determined from urinary excretion rate studies in EM subjects was 6.2 +/- 0.5 h (mean +/- SEM) with 95.5 +/- 6.0% of the dose recovered unchanged within 72 h. Similarly, in PM subjects t1/2 = 6.5 +/- 0.9 h and recovery 89.9 +/- 4.5%. 3. For orally administered 13-Hydroxylupanine (37.83 mumol) the t1/2 in EM subjects was 6.8 +/- 1.0 h with a recovery of 100.5 +/- 5.3%, and in PM subjects t1/2 = 5.9 +/- 1.6 h with a recovery of 102.5 +/- 4.8%. 4. The t1/2s of both lupanine and 13-Hydroxylupanine respectively did not differ significantly between EM and PM phenotypes. In addition, total recovery of dose for both alkaloids was similar between phenotypes. 5. In most subjects, > 76% of lupanine and > 85% of 13-Hydroxylupanine was recovered as the unchanged compound. Significant apparent partial dehydroxylation of 13-hydroxy-lupanine was observed in one EM (14% of dose) and one PM (34% of dose) subject. 6. Overall, the finding of a high urinary recovery of unchanged lupanine or 13-Hydroxylupanine together with similar t1/2s for both alkaloids in EM and PM CYP2D6 phenotypes suggests that clinical toxicity is unlikely to result from the use of lupin seed in footstuffs.

Accumulation of quinolizidine alkaloids in plants and cell suspension cultures: genera lupinus, cytisus, baptisia, genista, laburnum, and sophora.[Pubmed: 17404991]

The patterns of quinolizidine alkaloids in cell cultures of 10 species of Fabaceae were analyzed by high-resolution GLC and GLC-MS and compared with the alkaloids present in the leaves of the respective plants. Lupanine was produced in all 10 cell suspension cultures as the main alkaloid. It was accompanied by sparteine, tetrahydrorhombifoline, 17-oxosparteine, 13-Hydroxylupanine, 4-hydroxylupanine, 17-oxolupanine, and 13-Hydroxylupanine esters as minor alkaloids in some species. The alkaloid patterns of the plants differed markedly in that alpha-pyridone alkaloids were the major alkaloids in the genera Cytisus, Genista, Laburnum and Sophora but were not accumulated in the cell cultures. These data further support the assumption that the pathway leading to lupanine is the basic pathway of quinolizidine alkaloids biosynthesis and that the other alkaloids are derived from lupanine.


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